阅读说明：本技术 感官改性剂 (Sensory modifier ) 是由 丹·S·加斯帕德 迈克尔·艾伦·莫滕森 亚当·T·察尔特 于 2020-04-03 设计创作，主要内容包括：本发明提供了一种感官改性剂,该感官改性剂可为甜菊醇糖苷组合物提供改变的感官属性,例如减轻的甜味余韵持续或减轻的苦味。一种此类感官改性剂包含盐级分和酸级分。该盐级分可包含单咖啡酰奎尼酸的盐和/或二咖啡酰奎尼酸的盐。该酸级分可包含单咖啡酰奎尼酸和/或二咖啡酰奎尼酸。该盐级分优选占感官改性剂的至少50重量％。(The present invention provides a sensory modifier that can provide a steviol glycoside composition with altered sensory attributes, such as reduced lingering sweet aftertaste or reduced bitterness. One such sensory modifier comprises a salt fraction and an acid fraction. The salt fraction may comprise a salt of monocaffeoylquinic acid and/or a salt of dicaffeoylquinic acid. The acid fraction may comprise monocaffeoylquinic acid and/or dicaffeoylquinic acid. The salt fraction preferably constitutes at least 50 wt.% of the sensory modifier.)

1. A steviol glycoside composition, which composition comprises:

a steviol glycoside component; and

a sensory modifier in an amount effective to reduce lingering sweet aftertaste, reduce bitterness, or both;

wherein the weight ratio of a) the steviol glycoside component to sensory modifier is from 1: 0.3 to 1: 3; or b) the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight, preferably from 50% to 90%, from 50% to 80% or from 60% to 90% by weight of the sensory modifier is in the salt form.

2. A steviol glycoside composition, which composition comprises:

a steviol glycoside component; and

a sensory modifier in an amount effective to reduce lingering sweet aftertaste, reduce bitterness, or both,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, and

wherein the weight ratio of a) the steviol glycoside component to sensory modifier is from 1: 0.3 to 1: 3; or b) the salt fraction constitutes at least 50 wt.% of the sensory modifier, preferably 50 to 90 wt.%, 50 to 80 wt.%, or 60 to 90 wt.% of the sensory modifier.

3. The steviol glycoside composition of claim 1 or claim 2, wherein the sensory modifier comprises one or more of: 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, 5-O-caffeoylquinic acid, 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid or 4, 5-dicaffeoylquinic acid and their salts.

4. A steviol glycoside composition according to claim 1, wherein the sensory modifier is a mixture of one or more monocaffeoylquinic acids or salts thereof and one or more dicaffeoylquinic acids or salts thereof.

5. The steviol glycoside composition of claim 2 or claim 4, wherein the monocaffeoylquinic acid is one or more of 3-O-caffeoylquinic acid, 4-O-caffeoylquinic acid, or 5-O-caffeoylquinic acid.

6. The steviol glycoside composition of claim 2 or claim 4, wherein the monocaffeoylquinic acid salt is one or more of a salt of 3-O-caffeoylquinic acid, a salt of 4-O-caffeoylquinic acid, or a salt of 5-O-caffeoylquinic acid.

7. The steviol glycoside composition of claim 2 or claim 4, wherein the dicaffeoylquinic acid is one or more of 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, or 4, 5-dicaffeoylquinic acid.

8. The steviol glycoside composition of claim 2 or claim 4, wherein the dicaffeoylquinic acid salt is one or more of a salt of 1, 3-dicaffeoylquinic acid, a salt of 1, 4-dicaffeoylquinic acid, a salt of 1, 5-dicaffeoylquinic acid, a salt of 3, 4-dicaffeoylquinic acid, a salt of 3, 5-dicaffeoylquinic acid, or a salt of 4, 5-dicaffeoylquinic acid.

9. A steviol glycoside composition according to any preceding claim, wherein 10% or more, 25% or more or 50% or more by weight of the sensory modifier is dicaffeoylquinic acid and salts thereof.

10. A steviol glycoside composition according to any preceding claim, wherein the sensory modifier is monocaffeoylquinic acid and a salt of monocaffeoylquinic acid: mixtures of dicaffeoylquinic acid and salts of dicaffeoylquinic acid in a ratio of from 3: 1 to 1: 20, in a ratio of from 3: 1 to 1: 3, in a ratio of from 2: 1 to 1: 2, in a ratio of from 3: 1 to 1: 1 or in a ratio of from 2: 1 to 1: 1.

11. A steviol glycoside composition according to any preceding claim, wherein the sensory modifier comprises from 40 to 60% by weight dicaffeoylquinic acid and salts thereof.

12. The steviol glycoside composition of any one of claims 1 and 3 to 9, wherein 50 to 90, 50 to 80, 60 to 90, 60 to 80, or 65 to 75 weight% of the sensory modifier is in salt form.

13. The steviol glycoside composition of any one of claims 1 and 3 to 9, wherein at least 10, at least 20, 20 to 40, or 25 to 35% by weight of the sensory modifier is in the acid form.

14. The steviol glycoside composition of any one of claims 2 to 11, wherein the salt fraction comprises at least 60 wt.% of the total sensory modifier.

15. The steviol glycoside composition of any one of claims 2 to 14, wherein the salt fraction comprises less than 90 wt.%, less than 80 wt.%, from 60 wt.% to 80 wt.%, or from 65 wt.% to 75 wt.% of the total sensory modifier.

16. The steviol glycoside composition of any one of claims 2 to 15, wherein the acid fraction comprises at least 10, at least 20, 20 to 40, or 20 to 40 weight percent of the total sensory modifier.

17. A steviol glycoside composition according to any preceding claim, wherein the sensory modifier comprises a sodium salt of caffeoylquinic acid, a potassium salt of caffeoylquinic acid or both.

18. A steviol glycoside composition according to any preceding claim, wherein the sensory modifier comprises a mixture of one or more potassium salts of caffeoylquinic acid and one or more sodium salts of caffeoylquinic acid.

19. A steviol glycoside composition according to any preceding claim, wherein the pH of the composition is greater than the pH at the half-equivalence point of the sensory modifier.

20. A steviol glycoside composition according to any preceding claim, wherein the pH of the composition is less than the pH at the equivalence point of the sensory modifier.

21. A steviol glycoside composition according to any preceding claim, wherein the pH of the composition is less than 4.0, for example from 1.7 to 4.0.

22. A steviol glycoside composition according to any preceding claim, wherein the pH of the composition is greater than 2.0 or greater than 2.5.

23. A steviol glycoside composition according to any preceding claim, wherein at least a portion of the sensory modifier is prepared from a plant source.

24. The steviol glycoside composition of claim 23, wherein the plant source is mate tea, rosemary, chicory, stevia, artichoke, coffee or a mixture thereof.

25. The steviol glycoside composition of any one of claims 1 to 22, wherein at least a portion of the sensory modifier is prepared from mate tea.

26. The steviol glycoside composition of any one of claims 1 to 22, wherein at least a portion of the sensory modifier is prepared from stevia rebaudiana.

27. The steviol glycoside composition of any preceding claim, wherein the steviol glycoside component comprises rebaudioside D, rebaudioside M or both.

28. The steviol glycoside composition of claim 1, wherein at least 80% or at least 90% by weight of the steviol glycoside component is rebaudioside M.

29. The steviol glycoside composition of any preceding claim, wherein the composition comprises from 100ppm to 1600ppm of the steviol glycoside component.

30. The steviol glycoside composition of any preceding claim, wherein the composition comprises at least 200ppm, at least 300ppm, from 200ppm to 1000ppm, or from 400ppm to 800ppm of the steviol glycoside component.

31. The steviol glycoside composition of any one of claims 1 to 29, wherein the composition comprises from 100ppm to 1600ppm of rebaudioside M.

32. The steviol glycoside composition of claim 1, wherein the composition comprises at least 200ppm, at least 300ppm, at least 500ppm, from 200ppm to 1000ppm, or from 400ppm to 800ppm of rebaudioside M.

33. A steviol glycoside composition according to any preceding claim, wherein the composition comprises from 100ppm to 1600ppm of the sensory modifier.

34. A steviol glycoside composition according to claim 1, wherein the composition comprises at least 200ppm, at least 300ppm, at least 500ppm, from 200ppm to 1000ppm or from 400ppm to 800ppm of the sensory modifier.

35. A steviol glycoside composition according to any preceding claim, wherein the composition comprises from 50ppm to 1400ppm of a salt of caffeoylquinic acid.

36. The steviol glycoside composition of any preceding claim, wherein the composition comprises at least 100ppm, at least 150ppm, at least 250ppm or from 100ppm to 900ppm of a salt of caffeoylquinic acid.

37. The steviol glycoside composition of claim 1, wherein the weight ratio of steviol glycoside component to sensory modifier is from 1: 0.3 to 1: 1.

38. The steviol glycoside composition of any one of claims 2 to 36, wherein the weight ratio of steviol glycoside component to organoleptic modifier is from 1: 0.3 to 1: 1.

39. The steviol glycoside composition of any preceding claim, wherein the amount effective to reduce sweet aftertaste lingering is determined by at least four panelists trained in tasting the steviol glycoside composition using the round table method using a scale of 0 to 6, wherein a score of 0 represents no sweet aftertaste lingering and a score of 6 represents extreme sweet aftertaste lingering, and wherein the sweet aftertaste lingering score is reduced by at least 1 unit, at least 2 units, or at least 3 units as compared to a control sample lacking the sensory modifier.

40. The steviol glycoside composition of claim 39, wherein the amount of sensory modifier reduces the sweet lingering score to less than 3 units compared to a control sample lacking the sensory modifier.

41. The steviol glycoside composition of any preceding claim, wherein the steviol glycoside composition has a reduced lingering sweet aftertaste as compared to a control sample lacking the sensory modifier.

42. A steviol glycoside composition according to any preceding claim, wherein the amount effective to reduce bitter taste is determined by at least four panelists trained in tasting the steviol glycoside composition using the round table method on a scale of 0 to 6, wherein a score of 0 indicates no bitter taste and a score of 6 indicates extreme bitter taste, and wherein the bitter taste score is reduced by at least 1 unit, at least 2 units or at least 3 units as compared to a control sample lacking the sensory modifier.

43. The steviol glycoside composition of claim 42, wherein the amount of sensory modifier reduces bitterness score to less than 2 units or less than 1 unit as compared to a control sample lacking the sensory modifier.

44. The steviol glycoside composition of any preceding claim, wherein the steviol glycoside composition has a reduced bitterness as compared to a control sample lacking the sensory modifier.

45. A steviol glycoside composition according to any preceding claim, wherein the composition is an aqueous solution.

46. A steviol glycoside composition according to any preceding claim, wherein the composition is in solid form.

47. A steviol glycoside composition according to any preceding claim, wherein the concentration of the steviol glycoside component is from 200ppm to 1000ppm and the sensory modifier is from 200ppm to 1000 ppm.

48. A steviol glycoside composition according to any preceding claim, wherein the concentration of the steviol glycoside component is from 400ppm to 800ppm and the sensory modifier is from 400ppm to 800 ppm.

49. A beverage comprising the steviol glycoside composition of any preceding claim.

50. A method for reducing the undesirable sensory attributes of an aqueous solution of steviol glycosides, which method comprises preparing an aqueous solution of a composition according to any preceding claim.

51. The method of claim 50, wherein the undesirable sensory attribute is bitterness, lingering sweetness linger, sharp taste, poor mouthfeel, astringency, or a rebaudioside M type attribute, or any combination thereof.

52. A method for reducing lingering sweet aftertaste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with an sensory modifier in an amount effective to reduce lingering sweet aftertaste of the steviol glycoside component,

wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form.

53. A method for reducing lingering sweet aftertaste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component with an sensory modifier in an amount effective to reduce lingering sweet aftertaste of the steviol glycoside component,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, and

wherein the salt fraction comprises at least 50 wt% of the total sensory modifier.

54. A method for reducing bitter taste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce the bitter taste of the steviol glycoside component,

wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in salt form.

55. A method for reducing bitter taste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce the bitter taste of the steviol glycoside component,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, and

wherein the salt fraction comprises at least 50 wt% of the total sensory modifier.

56. A method according to any one of claims 52 to 55, wherein the steviol glycoside component and the sensory modifier are added simultaneously.

57. An aqueous steviol glycoside solution having a reduced lingering sweet aftertaste, the aqueous steviol glycoside solution comprising:

a steviol glycoside component comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside A, wherein the total steviol glycoside component concentration is from 200ppm to 1000 ppm; and

a sensory modifier at a concentration of 200ppm to 1000ppm,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid,

wherein the salt fraction comprises from 50 wt% to 80 wt% of the total sensory modifier, wherein at least a portion of the sensory modifier is prepared from mate tea or stevia and

wherein the aqueous steviol glycoside solution has a reduced lingering sweet taste as compared to an aqueous steviol glycoside solution having the same concentration of the same steviol glycoside component without the sensory modifier.

58. An aqueous steviol glycoside solution having reduced bitter taste, comprising:

a steviol glycoside component comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside A, wherein the total steviol glycoside component concentration is from 400ppm to 800 ppm; and

a sensory modifier at a concentration of 400ppm to 800ppm,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid,

wherein the salt fraction comprises from 50 wt% to 80 wt% of the total sensory modifier and the acid fraction comprises from 20 wt% to 50 wt% of the total sensory modifier,

wherein at least a portion of the sensory modifier is prepared from mate tea or stevia rebaudiana, and

wherein the aqueous steviol glycoside solution has a reduced bitterness as compared to an aqueous steviol glycoside solution having the same concentration of the same steviol glycoside component without the sensory modifier.

59. A steviol glycoside composition comprising:

from about 200ppm to about 800ppm of a steviol glycoside component comprising rebaudioside D and rebaudioside M, wherein rebaudioside M comprises at least 80% by weight of the steviol glycoside component; and

from about 200ppm to about 400ppm of a sensory modifier, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight, preferably from 50% to 90%, from 50% to 80% or from 60% to 90% by weight of the sensory modifier is in the salt form.

Background

Steviol glycosides are a sweet class of glycosylated diterpene compounds, often obtained from the leaves of Stevia rebaudiana (Stevia rebaudiana). Various steviol glycosides are known, some of which provide sugar-like mouthfeel characteristics and are 150 to 450 times sweeter than sugar. Such compounds are typically characterized by a single steviol backbone and the presence of different arrangements of glycoside carbohydrate residues at positions C13 and C19.

Over the last several decades, consumers have increasingly sought low calorie alternatives to calorie-rich products. Steviol glycosides provide non-caloric substitutes for traditional caloric sweeteners such as sugar, glucose, sucrose, and/or fructose. However, in some instances, consumers may recognize that the sensory and temporal mouthfeel characteristics of steviol glycosides differ to some extent from traditional caloric sweeteners. For example, existing steviol glycoside compositions may provide relatively reduced sweetness intensity, enhanced lingering sweet aftertaste, accentuated bitterness, and unfamiliar organoleptic attributes (such as astringency and metallic taste) when compared to traditional sweeteners. These sensory attributes may limit the use of steviol glycosides in various consumer products, particularly those that attempt to use the highest concentrations of steviol glycosides. At the same time, consumers prefer steviol glycosides as low calorie sweeteners, in part because of the potential of such compounds to be naturally derived from plant sources.

Disclosure of Invention

The present disclosure provides, among other things, compositions containing a steviol glycoside component and an amount of an organoleptic modifier effective to reduce the lingering of a sweet aftertaste, reduce bitterness, or otherwise improve the organoleptic properties of the steviol glycoside component. The steviol glycoside component contains one or more steviol glycosides. The sensory modifier comprises one or more caffeoylquinic acids. One part of the sensory modifier is in the salt form (corresponding to the "salt fraction") and the other part is in the acid form (corresponding to the "acid fraction"). In various aspects, at least 50% by weight of the sensory modifier is in the salt form. The sensory modifier may also be characterized as having a salt fraction of at least 50 wt% of the total sensory modifier. Surprisingly, it has been found that the combination of the acid and salt forms reduces bitterness and reduces lingering sweet aftertaste, and mixtures with less than 50 mole% salt may not provide the same advantages, and mixtures with more than 90 mole% salt may provide lingering sweet aftertaste with only a slight reduction. The disclosure also provides compositions and methods of use thereof.

For example, the present disclosure provides a steviol glycoside composition having reduced lingering sweet aftertaste, which composition comprises a steviol glycoside component and an amount of a sensory modifier effective to reduce lingering sweet aftertaste, wherein the sensory modifier comprises one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the salt form.

The present disclosure also provides a steviol glycoside composition having reduced bitterness comprising a steviol glycoside component and an amount of sensory modifier effective to reduce sweetness, wherein the sensory modifier may comprise one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the salt form.

The present disclosure also provides a method for reducing lingering sweet aftertaste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce lingering sweet aftertaste of the steviol glycoside component, wherein the organoleptic modifier comprises one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the organoleptic modifier is in the salt form.

The present disclosure also provides a method for reducing bitterness from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of sensory modifier effective to reduce bitterness of the steviol glycoside component, wherein the sensory modifier comprises one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the form of a salt.

The present disclosure also provides an aqueous steviol glycoside solution with reduced lingering of sweet aftertaste, comprising: a steviol glycoside component comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside a, wherein the total steviol glycoside concentration is from 200ppm to 1000 ppm; and a sensory modifier at a concentration of 200ppm to 1000ppm, wherein the sensory modifier comprises a salt fraction and an acid fraction, wherein the salt fraction (in one embodiment) comprises a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid, wherein the acid fraction comprises monocaffeoylquinic acid and dicaffeoylquinic acid, wherein the salt fraction comprises from 50% to 80% by weight of the total sensory modifier, wherein at least a portion of the sensory modifier (in one embodiment) is prepared from mate tea or stevia, and wherein the aqueous steviol glycoside solution has a reduced lingering sweet taste as compared to an aqueous steviol glycoside solution having the same concentration of the same steviol glycoside component without the sensory modifier.

The present disclosure also provides an aqueous steviol glycoside solution with reduced bitter taste, the composition comprising: a steviol glycoside component comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside a, wherein the total steviol glycoside component concentration is from 400ppm to 800 ppm; and a sensory modifier at a concentration of 400ppm to 800ppm, wherein the sensory modifier comprises a salt fraction and an acid fraction, wherein the salt fraction (in one embodiment) comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid, wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, wherein the salt fraction corresponds to 50% to 80% by weight of the total sensory modifier, and the acid fraction corresponds to 20% to 50% by weight of the total sensory modifier, wherein at least a portion of the total sensory modifier (in one embodiment) is prepared from mate tea or stevia, and wherein an aqueous steviol glycoside solution has a reduced bitterness as compared to an aqueous steviol glycoside solution having the same concentration of the same steviol glycoside component without sensory modifier.

The advantages achieved by embodiments of the present disclosure, some of which are unexpected. In various embodiments, the use of the sensory modifiers described herein improves various sensory attributes of the steviol glycoside component compared to the same steviol glycoside component without the sensory modifier. For example, the sensory modifier can provide a fuller mouthfeel profile, reduced lingering sweetness linger, a sucrose-like mouthfeel, reduced bitterness, or a combination thereof, as compared to the steviol glycoside component alone. In some embodiments, the sensory modifier can suppress undesirable sensory attributes typical of Reb M and Reb N, such as astringency, metallic flavor, powder sensation, numbing sensation, or vapor sensation.

In various embodiments, the use of a sensory modifier with a salt fraction of 50% by weight or more of the total sensory modifier has the advantage of providing a reduced bitterness and/or a reduced lingering sweet aftertaste of the steviol glycoside component compared to a salt fraction of less than 50% by weight. In further embodiments, use of a sensory modifier with a salt fraction of 90 wt.% or less of the total sensory modifier can provide a reduced lingering sweet aftertaste compared to use of a sensory modifier with a salt fraction of greater than 90 wt.%.

Drawings

The drawings illustrate generally, by way of example, but not by way of limitation, various embodiments discussed herein.

Figure 1 shows the structures of various steviol glycosides.

Figure 2 shows a simplified titration curve showing how changes in the acid and salt fractions do not necessarily correlate with changes in pH, even in a simple example.

It should be understood that numerous other modifications and examples can be devised by those skilled in the art that will fall within the scope and spirit of the principles of this disclosure.

Detailed Description

Reference will now be made in detail to certain embodiments of the disclosed subject matter, examples of which are illustrated in part in the accompanying drawings. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the exemplified subject matter is not intended to limit the claims to the disclosed subject matter.

In this document, the terms "a," "an," or "the" are used to include one or more than one unless the context clearly dictates otherwise. The term "or" is used to refer to a non-exclusive "or" unless otherwise indicated. All publications, patents, and patent documents cited in this document are incorporated by reference herein in their entirety as if individually incorporated by reference. Usage in the incorporated references should be considered supplementary to usage in this document if usage is inconsistent between this document and those documents so incorporated by reference; for irreconcilable inconsistencies, the usage in this document controls.

The recitation of values by range format is to be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited. For example, a range of "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only about 0.1% to about 5%, but also include individual values (e.g., 1%, 2%, 3%, and 4%) and sub-ranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range. Unless otherwise indicated, the statement "about X to Y" has the same meaning as "about X to about Y". Likewise, unless otherwise indicated, the statement "about X, Y or about Z" has the same meaning as "about X, about Y, or about Z".

Ppm (parts per million) is based on weight unless explicitly indicated.

The present disclosure relates to various steviol glycoside compositions having improved sensory attributes, such as reduced lingering of sweet aftertaste and/or reduced bitterness. The present disclosure also relates generally to sensory modifiers and uses thereof. In various embodiments, the sensory modifier comprises one or more caffeoyl-substituted quinic acids and salts thereof, wherein at least 50% by weight of the total sensory modifier is in the salt form. The present disclosure also relates to methods of mitigating undesirable attributes associated with various steviol glycoside components, and methods of providing improved compositions relative to steviol glycoside compositions without organoleptic modifiers described herein.

Steviol glycosides

The present disclosure provides such compositions: the composition contains a steviol glycoside component and has various improvements for altering its sensory perception. The steviol glycoside components of the present disclosure may contain a variety of steviol glycosides.

The steviol glycoside component may comprise one or more steviol glycosides. In some aspects, the term "steviol glycoside" refers to rebaudioside A (CAS #58543-16-1), rebaudioside B (Reb B) (CAS #58543-17-2), rebaudioside C (Reb C) (CAS #63550-99-2), rebaudioside D (Reb D) (CAS #63279-13-0), rebaudioside E (Reb E) (CAS #63279-14-1), rebaudioside F (Reb F) (CAS #438045-89-7), rebaudioside M (Reb M) (CAS #1220616-44-3), rubusoside (CAS #63849-39-4), dulcoside A (CAS #64432-06-0), rebaudioside I (Reb I) (MassBank record: 000FU 332), rebaudioside Q (Reb Q), (Reb N), rebaudioside N (N), and rebaudioside D (REb), Rebaudioside O (Reb O), 1, 2-stevioside (CAS #57817-89-7), 1, 3-stevioside (Reb G), steviol-1, 2-diglycoside (MassBank record: FU000299), steviol-1, 3-diglycoside, steviol-13-O-glucoside (13-SMG), steviol-19-O-glucoside (19-SMG), OPS1-5 (corresponding to Compound 4 from WO 100689), steviol glycosides having 1, 2, 3, 4, 5, 6,7, 8, 9, 10 or more glycosides, and isomers thereof. See fig. 1. See also "Steviol Glycosides Chemical and Technical Association" by Harriet Wallin (Food age. OrR.), 82 nd JECFA conference, 2016.

Steviol glycosides generally have the formula shown in FIG. 1, wherein steviol (R)₁And R₂Is H) is an aglycone backbone, and R₁And R₂Each may be hydrogen or one or more sugar moieties. The most common of these sugar moieties are glucose, rhamnose or xylitol, but steviol glycosides have been reported to include fructose and deoxyglucose moieties.

Steviol glycosides are not only structurally different, but also the organoleptic properties of the various steviol glycosides may be different. For example, stevioside (comprising three glucose units) and rebaudioside a (comprising four glucose units) are more abundant in stevia extracts and have particular sweetness profiles. Both stevioside and rebaudioside a add sweetness, but can be perceived as having bitter attributes, particularly at higher concentrations. Rebaudioside a has a bitter taste profile that increases with increasing concentration, which may limit its use at higher concentrations (e.g., greater than 400 ppm).

Other steviol glycosides may comprise increased amounts of glycosides and are present in stevia extracts in much lower abundance. Such compounds may sometimes be referred to as "secondary" steviol glycosides, even when they are used as the primary component in the composition. For example, so-called minor steviol glycosides may include rebaudioside D and rebaudioside M, which are present in stevia extracts in lower abundance and have different sweetness profiles than the more abundant steviol glycosides. Some of the sweetness attributes of these secondary steviol glycosides may be preferred over the primary steviol glycosides. For example, rebaudioside D and rebaudioside M have reduced bitterness profile compared to rebaudioside a. These reduced bitterness attributes of rebaudioside D and rebaudioside M allow for a more favorable sensory experience and enable their use at higher concentrations. However, although the bitterness of rebaudioside D and rebaudioside M is reduced compared to rebaudioside a, the perception of bitterness can still be a limiting factor, particularly at higher concentrations. Other organoleptic attributes may also be limiting factors, for example, sweet aftertaste lingering may be limiting in these minor glycosides, especially at higher concentrations. The lingering sweet aftertaste can be perceived as a longer residence time of the sweet taste in the mouth than would be expected for a comparable sugar solution. The lingering sweet aftertaste of secondary steviol glycosides can limit their use, particularly at higher concentrations.

As described herein, the addition of the sensory modifier can alter the sensory attributes of the steviol glycoside composition. In addition, sensory modifiers can alter the sensory attributes associated with a particular steviol glycoside component. For example, sensory modifiers can surprisingly reduce the lingering sweet aftertaste in minor steviol glycosides, such as rebaudioside D and rebaudioside M. By mitigating the lingering sweet aftertaste, the sensory modifier may allow for a more favorable sensory experience with the secondary steviol glycoside and allow for the use of the secondary steviol glycoside at higher concentrations. Thus, the disclosed sensory modifiers can alter the sensory attributes associated with the secondary steviol glycosides.

In some aspects, the secondary steviol glycosides may also have particular sensory attributes associated with sweetness intensity. The perceived sweetness intensity may be reported as SEV (sucrose equivalent value), wherein an increase in sweetness intensity corresponds to a higher SEV. An SEV of 1 corresponds to a 1% sucrose solution, an SEV of 2 corresponds to a 2% sucrose solution, and so on. Although the perception of sweetness intensity generally increases with increasing concentration of the secondary steviol glycoside, the perceived sweetness intensity can plateau as it levels off despite increasing amounts of the secondary steviol glycoside. This sweetness intensity plateau may limit the use of secondary steviol glycosides, particularly where higher SEV is desired. It has been found that the addition of sensory modifiers surprisingly increases the perceived sweetness intensity of the secondary steviol glycosides above the commonly observed plateau and enables trace amounts of steviol glycosides to be used at higher concentrations than previously used. For example, by combining rebaudioside M and one or more sensory modifiers, a sweetness intensity greater than SEV 11 can be achieved. In various embodiments, increasing the concentration of rebaudioside M and one or more sensory modifiers can achieve an increase in sweetness intensity up to about SEV 13 at about 1400ppm of rebaudioside M; thus, the disclosed sensory modifiers can increase the sweetness intensity associated with the secondary steviol glycosides above that which would be perceived in the absence of the sensory modifier.

In various embodiments, the steviol glycoside component may comprise a mixture of two or more steviol glycosides, one of which predominates. For example, the steviol glycoside component may be predominantly rebaudioside M, rebaudioside N, rebaudioside D or rebaudioside a. The predominant steviol glycoside may constitute at least or about 50, 60, 70, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, or 99.5 wt% of the steviol glycoside component.

Exemplary steviol glycoside components may comprise rebaudioside M, rebaudioside N, rebaudioside D and rebaudioside a. In some aspects, one or more of the steviol glycosides are isolated from Stevia rebaudiana (Stevia rebaudiana). In some aspects, one or more of the steviol glycoside components are produced by fermentation of an engineered microorganism or enzymatically produced from a plant-derived steviol glycoside and further isolated. For example, rebaudioside D and M may be produced by an engineered organism and then separated to produce the steviol glycoside components, predominantly rebaudioside D and rebaudioside M, as the predominant steviol glycoside species. In some aspects, one or more of the steviol glycosides are produced by bioconversion of enzymes and leaf extracts.

In other aspects, the steviol glycoside compositions and steviol glycoside components may comprise rebaudioside D and rebaudioside M in amounts greater than other steviol glycosides.

Rebaudioside M, rebaudioside D, or both may be present in the steviol glycoside component in a total amount of about 80 wt.% or more (e.g., RM80), 90 wt.% or more (e.g., RM90), 95 wt.% or more (e.g., RM95), or 99 wt.% or more of the total amount of steviol glycosides in the steviol glycoside component. Rebaudioside M may be the predominant steviol glycoside in the steviol glycoside component, and may be present in an amount ranging, for example, from about 50% to about 95%, from about 70% to about 90%, or from about 75% to about 85% of the total amount of steviol glycosides in the steviol glycoside component. Rebaudioside D may be in an amount less than rebaudioside M, such as in an amount ranging from about 5% to about 25%, from about 10% to about 20%, or from about 10% to about 15% of the total amount of steviol glycosides in the steviol glycoside component. For example, the composition may predominantly comprise rebaudioside M and/or D, and may comprise one or more of rebaudioside a, rebaudioside B, or stevioside in an amount of about 5 wt.% or less, about 2 wt.% or less, or about 1 wt.% or less of the total amount steviol glycosides in the steviol glycoside component.

The steviol glycoside compositions may comprise various amounts of steviol glycosides. The steviol glycosides may be present in the composition in any amount required for a particular use. For example, steviol glycosides may be present in the composition at a total steviol glycoside concentration of from about 1ppm to about 1000ppm or from about 1ppm to about 2000 ppm; such concentrations may be particularly useful in the case where the composition is a beverage or food composition. In some aspects, steviol glycosides may be present in the composition at a total steviol glycoside concentration of about 100ppm to about 2000ppm, about 200ppm to about 2000ppm, 300ppm to about 2000ppm, 400ppm to about 2000ppm, 500ppm to about 2000ppm, 600ppm to about 2000ppm, 700ppm to about 2000ppm, 800ppm to about 2000ppm, 900ppm to about 2000ppm, or 1000ppm to about 2000 ppm. In some aspects, steviol glycosides can be present in the composition at a total steviol glycoside concentration equal to or greater than about 10ppm, 100ppm, 200ppm, 300ppm, 400ppm, 500ppm, 600ppm, 700ppm, 800ppm, 900ppm, 1000ppm, 110ppm, 1200ppm, 1300ppm, 1400ppm, 1500ppm, 1600ppm, 1700ppm, 1800ppm, 1900ppm, or 2000 ppm. In some aspects, steviol glycosides may be present in the composition at a total steviol glycoside concentration of about 100ppm to about 1000ppm, about 200ppm to about 1000ppm, 300ppm to about 1000ppm, 400ppm to about 1000ppm, 500ppm to about 1000ppm, 600ppm to about 1000ppm, 700ppm to about 1000ppm, 800ppm to about 1000ppm, or 900ppm to about 1000 ppm. In some aspects, steviol glycosides may be present in the composition at a total steviol glycoside concentration of about 100ppm to about 800ppm, about 200ppm to about 800ppm, 300ppm to about 800ppm, 400ppm to about 800ppm, 500ppm to about 800ppm, 600ppm to about 800ppm, or 700ppm to about 800 ppm. In some aspects, the steviol glycosides may be present in the composition at a total steviol glycoside concentration of from about 400ppm to about 800 ppm.

The steviol glycoside component may comprise various amounts of one or more individual steviol glycoside substances, each of which may be present independently at a defined concentration for each substance. For example, the individual steviol glycoside substances may be present in the composition in a concentration of from about 1ppm to about 1000ppm or from about 1ppm to about 2000 ppm. In some aspects, the individual steviol glycoside species may be present in the composition at a concentration of from about 100ppm to about 2000ppm, from about 200ppm to about 2000ppm, from 300ppm to about 2000ppm, from 400ppm to about 2000ppm, from 500ppm to about 2000ppm, from 600ppm to about 2000ppm, from 700ppm to about 2000ppm, from 800ppm to about 2000ppm, from 900ppm to about 2000ppm, or from 1000ppm to about 2000 ppm.

For example, Reb a, Reb M, Reb D, or any combination thereof, if present, may each individually have a concentration of about 1ppm to about 1400ppm, or about 1ppm to about 1000 ppm. In some aspects, Reb a, Reb M, Reb D, or any combination thereof, can each be individually present in the composition at a concentration of about 100ppm to about 1000ppm, about 200ppm to about 1000ppm, 300ppm to about 1000ppm, 400ppm to about 1000ppm, 500ppm to about 1000ppm, 600ppm to about 1000ppm, 700ppm to about 1000ppm, 800ppm to about 1000ppm, 900ppm to about 1000 ppm. In some aspects, Reb a, Reb M, Reb D, or any combination thereof, can each individually be present in the steviol glycoside composition at a concentration equal to or greater than about 10ppm, 50ppm, 100ppm, 200ppm, 300ppm, 400ppm, 500ppm, 600ppm, 700ppm, 800ppm, 900ppm, or 1000 ppm. In some aspects, Reb a, Reb M, Reb D, or any combination thereof, can each be present in the composition individually at a concentration of about 100ppm to about 800ppm, about 200ppm to about 800ppm, 300ppm to about 800ppm, 400ppm to about 800ppm, 500ppm to about 800ppm, 600ppm to about 800ppm, or 700ppm to about 800 ppm. In some aspects, Reb a, Reb M, Reb D, or any combination thereof may be present in the composition at a concentration of about 400ppm to about 800 ppm.

Sensory modifier

Organoleptic modifiers are compounds or compositions that alter the organoleptic properties or organoleptic attributes of a sweetened consumable (e.g., a beverage, food product, etc.) in an amount. Non-limiting examples of sensory characteristics that the sensory modifier can alter include bitter, sour, tingling, astringent, metallic, sweet, dry, sweet, temporal aspects of sweet, and flavor notes such as licorice, vanilla, dried plum, marshmallow, and molasses flavor notes. Sensory modifiers can enhance sensory properties, such as enhancing sweetness; can inhibit organoleptic properties, such as reducing bitterness; or the temporal aspect of the organoleptic properties may be altered, for example, by mitigating sweet lingering or a combination thereof. In some embodiments, the amount employed in a composition having a plurality of steviol glycosides and one or more sensory modifiers alters at least one sensory characteristic, e.g., the composition may have a reduced bitterness or sweetness compared to one or more of the steviol glycosides in the composition, which results in a better than expected sensory characteristic in the composition.

In one embodiment, the present disclosure provides a sensory modifier comprising one or more caffeoyl-substituted quinic acids and salts thereof. In various embodiments, caffeoyl-substituted quinic acids include esters of carboxylic acids derived from caffeic acid and alcohols of quinic acid. As used herein, the term "caffeoyl-substituted quinic acid" or "caffeoyl-quinic acid" includes mono-and dicaffeoylquinic acids and salts thereof. Monocaffeoylquinic acid includes esters derived from a single caffeic acid and quinic acid (e.g., chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), and cryptochlorogenic acid (4-O-caffeoylquinic acid) dicaffeoylquinic acid includes esters derived from two caffeic acids and quinic acid (e.g., 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, and 4, 5-dicaffeoylquinic acid) thus, the sensory modifier comprises both acid and salt forms of caffeoyl-substituted quinic acids the free acid forms of the various caffeoyl-substituted quinic acids are shown in table 1.

TABLE 1 Structure of various caffeoyl-substituted quinic acids。

In various embodiments, the sensory modifier further comprises one or more of the following: quinic acid, caffeic acid, ferulic acid, sinapic acid, p-coumaric acid, esters of quinic acid, esters of caffeic acid, esters of ferulic acid, esters of sinapic acid, esters of p-coumaric acid, esters of caffeic acid and quinic acid containing more than one caffeic acid moiety, esters of ferulic acid and quinic acid containing a single ferulic acid moiety, esters of ferulic acid and quinic acid containing more than one ferulic acid moiety, esters of sinapic acid and quinic acid containing a single sinapic acid moiety, esters of sinapic acid and quinic acid containing more than one sinapic acid moiety, esters of p-coumaric acid and quinic acid containing a single p-coumaric acid moiety, esters of p-coumaric acid and quinic acid containing more than one p-coumaric acid moiety, A quinic acid diester containing one caffeic acid moiety and one ferulic acid moiety, a caffeate of 3- (3, 4-dihydroxyphenyl) lactic acid, a caffeate of tartaric acid containing more than one caffeic acid moiety and/or isomers thereof and corresponding salts thereof.

In some aspects, the sensory modifier comprises one or more of the following: chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), cryptochlorogenic acid (4-O-caffeoylquinic acid), 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, 4, 5-dicaffeoylquinic acid, 3-O-feruloylquinic acid, 4-O-feruloylquinic acid, 5-O-feruloylquinic acid, 1, 3-diferuoylquinic acid, 1, 4-diferuoylquinic acid, 1, 5-diferuoylquinic acid, 3, 4-diferuoylquinic acid, 3, 5-diferuoylquinic acid, neochlorogenic acid (3-O-caffeoylquinic acid), cryptochlorogenic acid (4-O-caffeoylquinic acid), 3, 5-dicaffeoylquinic acid, 3, 4-diferuoylquinic acid, 3, 5-diferuoylquinic acid, and/or a, 4, 5-diferuloyl quinic acid, rosmarinic acid, caftaric acid (monocaffeoyltartaric acid), chicoric acid (dicaffeoyltartaric acid) and salts and/or their isomers and their corresponding salts.

In some embodiments, the sensory modifier consists essentially of one or more compounds selected from the group consisting of: chlorogenic acid (5-O-caffeoylquinic acid) and neochlorogenic acid (3-O-caffeine)Caffeoylquinic acid), cryptochlorogenic acid (4-O-caffeoylquinic acid), 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, and 4, 5-dicaffeoylquinic acid and any combination thereof, isomers thereof, and corresponding salts thereof. In various embodiments, one or more alcohols of the caffeoyl moiety are replaced with hydrogen or by C₁-C₁₀Alkyl (e.g., methyl, ethyl, propyl, etc.), C₁-C₁₀Alkenyl radical, C₆-C₁₀Aryl radical, C₂-C₁₀Acyl, acrylate, caffeoyl, o-coumaroyl, p-coumaroyl, m-coumaroyl, cinnamoyl, 4-hydroxycinnamoyl, feruloyl, isoferuloyl, sinapoyl, galloyl, sulfate, phosphate, or phosphonate substitutions. Thus, the modified and substituted caffeic acid moieties yield cinnamic acid, o-coumaroyl, p-coumaric acid, m-coumaric acid, ferulic acid, and their acyl and ester forms. In various embodiments, one or more alcohols of the quinic acid moiety are substituted with C₁-C₁₀Alkyl (e.g., methyl, ethyl, propyl, etc.), C₁-C₁₀Alkenyl radical, C₆-C₁₀Aryl radical, C₂-C₁₀Acyl, acrylate, caffeoyl, o-coumaroyl, p-coumaroyl, m-coumaroyl, cinnamoyl, 4-hydroxycinnamoyl, feruloyl, isoferuloyl, sinapoyl, galloyl, sulfate, phosphate, or phosphonate substitutions.

The sensory modifier may comprise one or more of the following: caffeate of 3- (3, 4-dihydroxyphenyl) lactic acid, caffeate of tartaric acid, ferulate of quinic acid or any other optionally substituted cinnamoyl ester of quinic acid other than caffeoylquinic acid. Examples of ferulic acid esters of quinic acid include 3-O-feruloylquinic acid, 4-O-feruloylquinic acid, 5-O-feruloylquinic acid, 1, 3-diferuloyylquinic acid, 1, 4-diferuloyylquinic acid, 1, 5-diferuloyylquinic acid, 3, 4-diferuloyylquinic acid, 3, 5-diferuloyylquinic acid, 4, 5-diferuloyylquinic acid, and combinations thereof. An example of a caffeate of 3- (3, 4-dihydroxyphenyl) lactic acid is rosmarinic acid. Examples of caffeic acid esters of tartaric acid include chicoric acid (dicaffeoyltartaric acid) and caftaric acid (monocaffeoyltartaric acid) and combinations thereof.

In an alternative embodiment, the sensory modifier is a mixture consisting of one or more of the following: caffeate of 3- (3, 4-dihydroxyphenyl) lactic acid, caffeate of tartaric acid, ferulate of quinic acid or any other optionally substituted cinnamoyl ester of quinic acid other than caffeoylquinic acid. Such organoleptic modifiers also comprise their salts so as to have a salt fraction and an acid fraction. Thus, it is also contemplated that each of the various embodiments described herein relating to caffeoylquinic acid and other sensory modifiers may be equally applicable to this alternative.

Caffeic acid has the following structure:

quinic acid has the following structure:

the structure provided above is D- (-) -quinic acid, and the numbers shown correspond to the current IUPAC numbering.

In various embodiments, the sensory modifier may be enriched in one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid. The term "enriched" refers to an increase in the amount of one of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid relative to one or more other compounds present in the sensory modifier. Sensory modifiers enriched in one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid may alter the sensory attributes of the steviol glycoside component of the composition.

Organoleptic modifiers enriched in one or more dicaffeoylquinic acids can alter the organoleptic properties of steviol glycoside compositions. The dicaffeoylquinic acid-enriched sensory modifier may comprise 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, 50% or more, 60% or more, 70% or more, 80% or more, or 90% or more of dicaffeoylquinic acid.

In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be monocaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be chlorogenic acid (5-O-caffeoylquinic acid) and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be neochlorogenic acid (3-O-caffeoylquinic acid) and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, or at least or about 50% by weight of the total sensory modifier can be cryptochlorogenic acid (4-O-caffeoylquinic acid) and salts thereof.

In various other embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be 1, 3-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be 1, 4-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be 1, 5-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be 3, 4-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be 3, 5-dicaffeoylquinic acid and salts thereof. In various embodiments, at least or about 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or at least or about 50% by weight of the total sensory modifier can be 4, 5-dicaffeoylquinic acid and salts thereof.

The weight ratio of total monocaffeoylquinic acid and salts thereof to total dicaffeoylquinic acid and salts thereof of the sensory modifier may, for example, be from 20: 1 to 1: 20 (e.g., from 3: 1 to 1: 20). In various embodiments, the sensory modifier has a weight ratio of monocaffeoylquinic acid and salts thereof to dicaffeoylquinic acid and salts thereof of from 15: 1 to 1: 15, from 10: 1 to 1: 10, from 5: 1 to 1: 5, from 3: 1 to 1: 3, from 2: 1 to 1: 2, from 1.5: 1 to 1: 1.5, from 5: 1 to 1: 1, from 3: 1 to 1: 1, from 2: 1 to 1: 1, from 1.5: 1 to 1: 1.1, from 1: 1 to 1: 20, from 1: 1 to 1: 15, from 1: 1 to 1: 10, from 1: 5 to 1: 20, from 1: 5 to 1: 15, from 1: 5 to 1: 10, from 1: 2 to 1: 20, from 1: 2 to 1: 15, from 1: 2 to 1: 10, from 1: 2 to 1: 5, from 1: 3, from 1: 2 to 1: 2, or from 1.5: 1. In some embodiments, the sensory modifier has a greater amount by weight of dicaffeoylquinic acid and salts of dicaffeoylquinic acid than the amount of monocaffeoylquinic acid and salts of monocaffeoylquinic acid. In various embodiments, the ratio of monocaffeoylquinic acid to dicaffeoylquinic acid (including their salts) of the sensory modifier is about 1: 1.

Salt forms of sensory modifiers

The sensory modifiers provided herein contain a moiety in the salt form (corresponding to the "salt fraction") and a moiety in the acid form (corresponding to the "acid fraction"). In various embodiments, the salt fraction comprises at least 50 wt% of the total sensory modifier. Thus, the main component is the compound in salt form, based on the weight of the total sensory modifier.

The sensory modifier may contain various types of salts, but will typically contain salts suitable for ingestion, typically containing salts derived from alkali metals (such as sodium and potassium), alkaline earth metals (such as magnesium and calcium), and nitrogen (such as amino acids).

As described herein, the sensory modifier comprises one or more caffeoyl-substituted quinic acids and their salt forms. Each salt of caffeoyl-substituted quinic acid may be a mixture of lithium, sodium, potassium, magnesium, calcium, ammonium salts, or any combination thereof. In various embodiments, each salt of caffeoyl-substituted quinic acid is a sodium salt, a potassium salt, or mixtures thereof. Thus, the sensory modifier may comprise a mixture of a sodium salt of monocaffeoylquinic acid, a sodium salt of dicaffeoylquinic acid, a potassium salt of monocaffeoylquinic acid, a potassium salt of dicaffeoylquinic acid, or any combination thereof. For example, the sensory modifier may comprise sodium and/or potassium salts of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, 4, 5-dicaffeoylquinic acid, or any combination thereof.

In various embodiments, the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the total sensory modifier is in the salt form.

For example, at least or about 50 wt%, 55 wt%, 60 wt%, 61 wt%, 62 wt%, 63 wt%, 64 wt%, 65 wt%, 66 wt%, 67 wt%, 68 wt%, 69 wt%, 70 wt%, 71 wt%, 72 wt%, 73 wt%, 74 wt%, 75 wt%, 80 wt%, 85 wt%, or at least or about 90 wt% of the total sensory modifier is in the form of a salt. In further embodiments, less than or about 60, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, or less than or about 90 weight percent of the total sensory modifier is in the form of a salt. In further embodiments, about 50% to 90%, 50% to 80%, 50% to 75%, 60% to 90%, 60% to 80%, 60% to 79%, 60% to 77%, 60% to 75%, 60% to 73%, 60% to 70%, 65% to 80%, 65% to 75%, 66% to 74%, 67% to 73%, 68% to 72%, 69% to 71%, 65% to 70%, 67% to 72%, 69% to 74%, or 70% to 75% by weight of the total sensory modifier is in salt form.

For example, at least or about 50, 55, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 80, 85, or at least or about 90 weight percent of the combined total of caffeoylquinic acid salt and caffeine quinic acid is in salt form. In further embodiments, less than or about 60, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, or less than or about 90 of the combined total of the salt of caffeoylquinic acid and caffeoylquinic acid is in the salt form. In further embodiments, about 50 to 90, 50 to 80, 50 to 75, 60 to 90, 60 to 80, 60 to 79, 60 to 77, 60 to 75, 60 to 73, 60 to 70, 65 to 80, 65 to 75, 66 to 74, 67 to 73, 68 to 72, 69 to 71, 65 to 70, 67 to 72, 69 to 74, or 70 to 75 weight percent of the combined total of caffeoylquinic acid salt and caffeoylquinic acid is in salt form. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.

As used herein, "salt form" refers to an ionizable compound in an anionic form so as to form an ion pair with a cation other than a hydrogen ion, such as a metal cation or a cationic ammonium compound. The compound may be a metal cation M⁺Or with ammonium compounds NR4⁺Ion-coordinated carboxylate-COO^-Wherein each R is H or alkyl. For example, in the solid state, the carboxylate may be ionically bound to the cation. Without being limited by theory, in solution, the ionic species may be tightly paired as a compact ion pair, or it may be isolated and solvated. However, when the dissolved salt form of the anion is separated from the solution, it is removed along with the paired cationic species. For example, after removing the carboxylic acid in salt form from the solution, the resulting compound will be a metal carboxylate salt or other ionic compound. In various embodiments, the salt form is an alkali metal salt, such as a sodium or potassium salt of one or more quinic acids. One difference in the differences between the salt form and the acid form is that the separation of the salt form results in an ionic compound that generally contains a metal cation, while the separation of the acid form results in a neutral species that is generally free of a metal cation. The salts and salt forms described herein may include mixed salts. Mixed salts include mixtures of two or more cationic species that share a common anionic partner, such as mixed potassium and sodium salts of caffeoylquinic acid.

As used herein, "acid form" refers to a carboxylic acid compound having a carboxylic acid group-COOH. In solution, -COOH can be deprotonated to provide ions that pair with protons or protonated speciesCarboxylate groups which are non-metallised but not metallised. Thus, the acid form may correspond to-COOH or-COO with a H + pair^-The compound of (1). For example, the dissolved acid form may provide a carboxylate that is electronically balanced by hydronium or other protonated solvent species, but the counterion is not a metal cation or ammonium salt. In the solid state, the acid form may be neutral and characterized as a fully covalent species.

In further examples, at least or about 5, 10, 15, 20, 25, 30, 35, 40, or at least or about 45 weight percent of the total sensory modifier is in the acid form. In further embodiments, less than or about 10, 15, 20, 25, 30, 35, 40, or less than about 50 weight percent of the total sensory modifier is in the acid form. In further embodiments, 5 to 50 wt%, 10 to 50 wt%, 15 to 50 wt%, 20 to 50 wt%, 5 to 40 wt%, 10 to 40 wt%, 15 to 40 wt%, 20 to 40 wt%, 5 to 35 wt%, 10 to 35 wt%, 20 to 35 wt%, 5 to 30 wt%, 10 to 30 wt%, 15 to 30 wt%, 20 to 30 wt%, 5 to 20 wt%, 10 to 20 wt%, 15 to 20 wt%, 5 to 15 wt%, 10 to 15 wt%, or 5 to 10 wt% of the total sensory modifier is in acid form.

In further examples, at least or about 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, or at least or about 45% by weight of the combined total amount of the salt of caffeoylquinic acid and caffeoylquinic acid is in the acid form. In further embodiments, less than or about 10, 15, 20, 25, 30, 35, 40, or less than about 50 weight percent of the combined total amount of the salt of caffeoylquinic acid and caffeoylquinic acid is in the acid form. In further embodiments, 5 to 50 weight%, 10 to 50 weight%, 15 to 50 weight%, 20 to 50 weight%, 5 to 40 weight%, 10 to 40 weight%, 15 to 40 weight%, 20 to 40 weight%, 5 to 35 weight%, 10 to 35 weight%, 15 to 35 weight%, 20 to 35 weight%, 5 to 30 weight%, 10 to 30 weight%, 15 to 30 weight%, 20 to 30 weight%, 5 to 20 weight%, 10 to 20 weight%, 15 to 20 weight%, 5 to 15 weight%, 10 to 15 weight%, or 5 to 10 weight% of the combined total amount of caffeoylquinic acid and caffeoylquinic acid is in acid form. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.

In various embodiments, the sensory modifier comprises a salt fraction and an acid fraction, wherein the salt fraction comprises one or more of a salt of monocaffeoylquinic acid and a salt of dicaffeoylquinic acid, wherein the acid fraction comprises one or more of monocaffeoylquinic acid and dicaffeoylquinic acid, and wherein the salt fraction comprises at least 50% by weight of the total sensory modifier.

For example, the salt fraction comprises at least or about 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, or at least or about 90 wt% of the total sensory modifier. In further embodiments, the salt fraction comprises less than or about 60%, 65%, 70%, 75%, 80%, 85% or less than or about 90% by weight of the total sensory modifier. In further embodiments, the salt fraction comprises from 50 wt% to 90 wt%, from 50 wt% to 80 wt%, from 50 wt% to 75 wt%, from 60 wt% to 90 wt%, from 60 wt% to 80 wt%, from 65 wt% to 80 wt%, or from 65 wt% to 75 wt% of the total sensory modifier. Unless otherwise indicated, the weight% of the salt fraction including the balancing cationic species should be calculated.

In further examples, the acid fraction comprises at least or about 5 wt%, 10 wt%, 15 wt%, 20 wt%, 25 wt%, 30 wt%, 35 wt%, 40 wt%, or at least or about 45 wt% of the total sensory modifier. In further embodiments, the acid fraction comprises less than or about 10, 15, 20, 25, 30, 35, 40, or less than about 50 weight percent of the total sensory modifier. In further embodiments, the acid fraction comprises 5 to 50 weight%, 10 to 50 weight%, 15 to 50 weight%, 20 to 50 weight%, 5 to 40 weight%, 10 to 40 weight%, 15 to 40 weight%, 20 to 40 weight%, 5 to 35 weight%, 10 to 35 weight%, 20 to 35 weight%, 5 to 30 weight%, 10 to 30 weight%, 15 to 30 weight%, 20 to 30 weight%, 5 to 20 weight%, 10 to 20 weight%, 15 to 20 weight%, 5 to 15 weight%, 10 to 15 weight%, or 5 to 10 weight% of the total sensory modifier.

As another example, the salt fraction comprises at least or about 50 wt%, 55 wt%, 60 wt%, 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, or at least or about 90 wt% of the combined total amount of the salt of caffeoylquinic acid and caffeoylquinic acid. In further embodiments, the salt fraction comprises less than or about 60%, 65%, 70%, 75%, 80%, 85%, or less than or about 90% by weight of the combined total amount of the salt of caffeoylquinic acid and caffeoylquinic acid. In further embodiments, the salt fraction comprises 50 to 90 wt%, 50 to 80 wt%, 50 to 75 wt%, 60 to 90 wt%, 60 to 80 wt%, 65 to 80 wt%, or 65 to 75 wt% of the combined total amount of the salt of caffeoylquinic acid and caffeoylquinic acid. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.

The sensory modifier may also be characterized in that at least 50 mole% of the total sensory modifier is in the salt form. For example, at least or about 50 mole%, 55 mole%, 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or at least or about 90 mole% of the total sensory modifier is in the salt form. In further embodiments, less than or about 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or less than or about 90 mole% of the total sensory modifiers are in the salt form. In further embodiments, 50 to 90, 50 to 80, 50 to 75, 60 to 90, 60 to 80, 60 to 75, 60 to 70, 65 to 80, or 65 to 75 mole% of the total sensory modifier is in the form of a salt.

In further examples, at least or about 5 mol%, 10 mol%, 15 mol%, 20 mol%, 25 mol%, 30 mol%, 35 mol%, 40 mol%, or at least or about 45 mol% of the total sensory modifier is in the acid form. In further embodiments, less than or about 10 mole%, 15 mole%, 20 mole%, 25 mole%, 30 mole%, 35 mole%, 40 mole%, or less than about 50 mole% of the total sensory modifiers are in the acid form. In further embodiments, 5 to 50 mole%, 10 to 50 mole%, 15 to 50 mole%, 20 to 50 mole%, 5 to 40 mole%, 10 to 40 mole%, 15 to 40 mole%, 20 to 40 mole%, 5 to 35 mole%, 10 to 35 mole%, 20 to 35 mole%, 5 to 30 mole%, 10 to 30 mole%, 15 to 30 mole%, 20 to 30 mole%, 5 to 20 mole%, 10 to 20 mole%, 15 to 20 mole%, 5 to 15 mole%, 10 to 15 mole%, or 5 to 10 mole% of the total sensory modifier is in acid form.

In further examples, at least 50 mole% of the sensory modifier (i.e., the combined total of the salt of caffeoylquinic acid and caffeoylquinic acid) is in the salt form. For example, at least or about 50 mole%, 55 mole%, 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or at least or about 90 mole% of the combined total of caffeoylquinic acid salt and caffeoylquinic acid is in the salt form. In further embodiments, less than or about 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or less than or about 90 mole% of the combined total of the salt of caffeoylquinic acid and caffeoylquinic acid is in the salt form. In further embodiments, 50 to 90 mole%, 50 to 80 mole%, 50 to 75 mole%, 60 to 90 mole%, 60 to 80 mole%, 60 to 75 mole%, 60 to 70 mole%, 65 to 80 mole%, or 65 to 75 mole% of the combined total of the salt of caffeoylquinic acid and caffeoylquinic acid is in the salt form. In some embodiments thereof, the salt is a sodium salt, a potassium salt, or both.

Similarly, the salt fraction can be characterized by mole% rather than weight%. In various embodiments, for example, the salt fraction comprises at least or about 50 mole%, 55 mole%, 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or at least or about 90 mole% of the total sensory modifier. In further embodiments, the salt fraction comprises less than or about 60 mole%, 65 mole%, 70 mole%, 75 mole%, 80 mole%, 85 mole%, or less than or about 90 mole% of the total sensory modifier. In further embodiments, the salt fraction comprises from 50 mol% to 90 mol%, from 50 mol% to 80 mol%, from 50 mol% to 75 mol%, from 60 mol% to 90 mol%, from 60 mol% to 80 mol%, from 65 mol% to 80 mol%, or from 65 mol% to 75 mol% of the total sensory modifier.

In further examples, the acid fraction comprises at least or about 5 mole%, 10 mole%, 15 mole%, 20 mole%, 25 mole%, 30 mole%, 35 mole%, 40 mole%, or at least or about 45 mole% of the total sensory modifier. In further embodiments, the acid fraction comprises less than or about 10 mole%, 15 mole%, 20 mole%, 25 mole%, 30 mole%, 35 mole%, 40 mole%, or less than about 50 mole% of the total sensory modifier. In further embodiments, the acid fraction comprises 5 to 50 mole%, 10 to 50 mole%, 15 to 50 mole%, 20 to 50 mole%, 5 to 40 mole%, 10 to 40 mole%, 15 to 40 mole%, 20 to 40 mole%, 5 to 35 mole%, 10 to 35 mole%, 20 to 35 mole%, 5 to 30 mole%, 10 to 30 mole%, 15 to 30 mole%, 20 to 30 mole%, 5 to 20 mole%, 10 to 20 mole%, 15 to 20 mole%, 5 to 15 mole%, 10 to 15 mole% or 5 to 10 mole% of the total sensory modifier.

The sensory modifier may, for example, have a weight or molar ratio of acid to salt of from 1: 1 to 1: 9, from 1: 1 to 1: 8, from 1: 1 to 1: 7, from 1: 1 to 1: 6, from 1: 1 to 1: 5, from 1: 1 to 1: 4, from 1: 1 to 1: 3, from 1: 1 to 1: 2, from 1: 1 to 1: 1.5.

The various mole%, weight ratios, mole ratios of the salt fractions and salt forms described herein can relate to the total sensory modifier, or in various embodiments, to a portion of the sensory modifier, such as a caffeoylquinic acid moiety, a monocaffeoylquinic acid moiety, a dicaffeoylquinic acid moiety, and corresponding salts.

The salt fraction, mole% and weight% of the salt form of the total sensory modifier can be determined by a variety of techniques available to the ordinarily skilled artisan. For example, the salt fraction, mole% and weight% of the total sensory modifier can be determined spectroscopically (e.g., NMR or ICP-MS), experimentally (e.g., by titration), or by calculation after determining the amount of each component added to the sensory modifier.

Each of the quinic acids described herein (including each of monocaffeoylquinic acid and dicaffeoylquinic acid) may be considered a weak acid, and they may each be present in at least one of their conjugate acid form, conjugate base form (e.g., in the form of a salt thereof), and mixed conjugate acid-conjugate base form, where a portion (e.g., a molar fraction) of the compound is present in the conjugate acid form and another portion is present in the conjugate base form. The fraction of conjugate acid forms to conjugate base forms of mono-and dicaffeoylquinic acids will depend on various factors, including the pKa of each compound and the pH of the composition.

In various embodiments, for example, in aqueous solution, the salt form of the total sensory modifier is present in equilibrium with the acid form. For example, a molecule in a particular salt form can be protonated and thus converted to the acid form, and the molecule in the acid form can be deprotonated to yield the salt form. Such interaction will not substantially alter the total weight% of a given form or fraction of the total sensory modifier after approaching or reaching equilibrium. For example, a composition having a salt fraction of 50% by weight or more of the total sensory modifier may maintain the same ratio of salt fraction to acid fraction even though various compounds may be exchanged from one fraction to another.

There are also situations where the equilibrium between the salt form and the acid form can shift in response to the addition of a component to the composition. For example, the addition of a buffer, salt, acid, or base can shift the equilibrium in favor of the salt fraction or acid fraction, thereby changing the weight% of the composition.

Furthermore, there may be a relationship between the pH of the composition and the ratio of salt fraction to acid fraction. For example, the salt fraction generally increases with increasing pH and generally decreases with decreasing pH. However, as shown in the titration curve of fig. 2, pH is a concept to distinguish between salt and acid fractions. This is clearly visible in the buffer of the titration curve, where a proportionally large change in the concentration of base (or acid) results in a very small or negligible change in pH. For example, an increase in the concentration of base does not meaningfully cause a rise in pH unless removal of the buffer is initiated. The titration curves of fig. 2 are simplified and compositions with more than one ionizable component will have more complex titration curves. The buffer is centered around a pH corresponding to the various pKa values of the compound or mixture being titrated. For reference, the pKa of quinic acid is about 3.46, while some quinic acid derivatives may have lower pKa. Common buffer solutions citric acid have pKa values (pKa1, pKa2, and pKa3) of about 3.10, 4.80, and 5.40, respectively. In various embodiments, the composition has a pH near the center of the buffer zone for the various caffeoylquinic acid compounds, such as a pH of from about 1 to about 4, from about 1 to about 3, from about 2 to about 4, from about 3 to about 4, from about 2 to about 3, from about 2.5 to about 3.5, from about 2.4 to about 3.6, from about 2.2 to about 3, from about 2.4 to about 3, from about 2.6 to about 3, from about 2.2 to about 3.2, from about 2.4 to about 3.4, from about 2.4 to about 3.2, from about 2.6 to about 3.0, from about 2.6 to about 3.4, from about 2.2 to about 2.9, from about 2.3 to about 3.1, from about 2.4 to about 3.2, from about 2.5 to about 2.9, from about 2.5 to about 3.6, from about 2.2 to about 2.9, from about 2.7.8 to about 2.9, or from about 2.4 to about 2.7.4. For example, the pH may be about 2.2, about 2.3, about 2.4, about 2.5, about 2.6, about 2.7, about 2.8, about 2.9, about 3.0, about 3.1, or about 3.2. In various other embodiments, the pH may be from about 3.2 to about 3.8, from about 3.3 to about 3.7, from about 3.3 to about 3.6, from about 3.4 to about 3.7, from about 3.4 to about 3.6, from about 3.4 to about 4, from about 3.4 to about 3.9, from about 3.4 to about 3.8, from about 3.4 to about 3.7, or from about 3.4 to about 3.6.

In further embodiments, the pH of the composition is less than or about 4, 3.9, 3.8, 3.7, 3.6, 3.5, 3.4, 3.3, 3.2, 3.1, 3.0, 2.9, 2.8, 2.7, 2.6, or 2.5. In further embodiments, the pH of the composition is greater than or equal to about 0.5, 0.75, 1, 1.5, 1.7, 2, 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 3, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, or 3.7. The pH value can be measured by, for example, an ISFET (ion-specific field effect transistor) meter.

In various other embodiments, the pH of the composition is greater than the half equivalence point of the total sensory modifier or the pH at Ka.

In various other embodiments, the pH of the composition is less than the pH at the equivalence point of the total sensory modifier.

In various other embodiments, for example in a solid composition, the salt form and the acid form can be solid, wherein the portion between the salt form and the acid form is solidified. It is to be understood that in various embodiments, the ratio of the salt fraction to the acid fraction in a solid composition (such as a granulated table sweetener) may be different than the ratio in the resulting solution to which the solid composition is added. For example, in some embodiments, a solid steviol glycoside composition, when dissolved, will result in a solution with sensory modifiers, at least 50% by weight of which are in the salt form.

An effective amount of an organoleptic modifier

The sweetness time profile of sucrose is considered highly desirable. The sweetness of some non-nutritive sweeteners, including rebaudioside a, is considered "stronger" than sucrose because its sweetness takes effect more slowly or longer. For example, it has a longer onset before any sweetness is perceived and then rapidly increases to maximum sweetness. Such slow-acting sweeteners may also be referred to as "sharp". In contrast, sucrose has a shorter onset time, but does not increase too quickly to maximum sweetness, which may be referred to as "rounded". Some non-nutritive sweeteners may have a longer duration of sweet aftertaste than sucrose, i.e., the flavor takes longer to dissipate from peak sweetness to a level where sweetness is no longer perceived. Sweetener compositions with sweetness temporal characteristics closer to sucrose are considered more desirable.

The compositions of the present disclosure comprise an amount of an organoleptic modifier effective to alter the organoleptic properties of one or more steviol glycosides in the steviol glycoside component. For example, the sensory attributes may be altered to more closely approximate the sensory characteristics of sucrose. In various embodiments, the sensory modifier is present in an amount effective to reduce the lingering sweet aftertaste, reduce the bitter taste, or both, of the steviol glycoside.

Sensory panel evaluations can be used to determine the amount of sensory modifier effective to reduce bitterness, reduce lingering sweetness linger, or both. Sensory panel evaluation is a scientific and reproducible method essential to the food science industry. Sensory panelists have involved a panel of three or more individual panelists. The panelist may be a trained, experienced, or even professional evaluator, but typically the panelist is not a consumer or a pre-evaluator for which criteria have not been determined (ii)assessor). Panelists were instructed to avoid the effects of personal subjectivity and enhance reproducibility according to industry accepted practices. For example, panelists will evaluate the objective sensory attributes of the tested products, but will not typically provide subjective attributesSuch as personal preferences. In various embodiments, sensory panel evaluations may be conducted by three, four, five or more panelists in a round table format, wherein the panelists discuss and evaluate each sensory attribute and agree on terms and attributes of each sample. The panel may provide a numerical scale to describe each attribute. For example, a zero may correspond to the attribute not being present, while another number (such as six) indicates that the upper extreme of the attribute is present. The round table format may also involve a panelist leader, directing discussions about terms and directing panelists to evaluate particular products and attributes.

For example, sensory panel evaluations or assays may be performed to characterize the sensory attributes of steviol glycoside compositions having various salt fractions of sensory modifiers. The organoleptic properties of the solution may be tested by a panel of at least three, but preferably four or more individuals experienced in tasting the steviol glycoside composition. Experienced panelists have experience in tasting steviol glycosides and are familiar with the sensory attributes of various steviol glycosides and steviol glycoside blends, including lingering sweet aftertaste and bitterness. These experienced panelists were also familiar with tasting steviol glycosides compared to the control sucrose solution. An experienced panelist may use a round table method to evaluate each sweetness profile. For example, to test each solution, an experienced panelist may dispense approximately 2mL of each solution into their mouth by pipette, dispense the solution by moving the tongue, and record the value of the particular sweetness attribute tested. For each sweetness attribute, the panelist agreed on a descriptive scale for each sweetness attribute, and then recorded the value of each sweetness attribute against that descriptive scale. If multiple solutions are tested in a secondary test, the panelist may purify the taste sensation with water. For example, a round table evaluation of sweet aftertaste lingering may specify a scale of 0 to 6, where a score of 0 indicates that no sweet aftertaste lingers, and a score of 6 indicates that extreme sweet aftertaste lingers. A round table assessment of bitterness may be assigned a scale of 0 to 6, where a score of 0 indicates a lingering sweet aftertaste, and a score of 6 indicates a lingering extreme sweet aftertaste (0: none, 1: weak, 2: slight, 3: moderate, 4: fixed, 5: strong, 6: extreme).

As another example, the sweetness intensity of a solution may be tested by a panel of at least four individuals who are experienced in tasting steviol glycoside compositions. Panelists may use sucrose solutions corresponding to the 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13% and 14% standard ranges of SEVs with values of 1, 2, 3, 4, 5, 6,7, 8%, 9%, 10%, 11%, 12%, 13% and 14%. To test each solution, an experienced panelist dispensed approximately 2mL of each solution into their own mouth by pipette, dispensed the solutions by moving the tongue, and recorded the SEV value of each solution based on comparison to 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13% and 14% sucrose solutions. Between tastings of different solutions, panelists were able to cleanse the taste with water. Panelists also had the option to taste sucrose solutions in the 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13% and 14% standard ranges between tasting test solutions to ensure that their recorded SEV values matched exactly with standard sucrose solutions.

The panelist may be a trained panelist. Trained panelists have been trained to understand the terminology and sensory phenomena associated with those sensory attributes associated with the products tested. For example, a panelist trained to test steviol glycoside compositions will understand the nomenclature and sensory phenomena of bitterness, lingering sweetness linger, astringency, the typical rebaudioside M and rebaudioside N phenomena, mouthfeel, tea/flower/green notes, and the sharp-rounded feel that can be produced by steviol glycoside compositions. In various embodiments, trained panelists have received training against reference samples corresponding to bitterness, lingering sweet aftertaste, astringency, typical rebaudioside M and rebaudioside N phenomena, mouthfeel, tea aroma/flower aroma/green notes, and a sharp-rounded sensation, and have therefore been calibrated to recognize and evaluate such criteria. Trained panelists have sufficient acuity to distinguish between the magnitude and nuances of various sensations.

Control samples are often used as reference points or for comparison purposes. For example, a control sample can be used to identify the effectiveness of the sensory modifier. The control sample may be a composition, such as a solution comprising the steviol glycoside component but in the absence of the organoleptic modifier. The control sample is otherwise identical except for the sensory modifier, and it should contain the same steviol glycoside component at the same concentration. Other standard samples are commonly used in sensory panelists, such as standard samples for assessing the intensity of sensory attributes. In other embodiments, the control sample may be a modified control sample containing different sensory modifiers such as competitive sensory modifiers for comparison purposes, sensory modifiers in all acid forms, or sensory modifiers in all salt forms.

The present disclosure is not limited to sensory testing by experienced or trained panelists. For example, untrained panelists may be utilized. However, with untrained panelists, a greater number of panelists are required to provide reproducible results, which will typically focus on subjective attributes such as preferences.

Additional exemplary sensory measures of sensory attributes and test criteria are described in the examples provided in this disclosure.

Additional description regarding round table sensory panels and sensory testing is shown in the following patent applications: PCT/US2018/054743 published as WO 2019/071220 on 11/4.2019; PCT/US2018/054691 published as WO 2019/071182 on 11/4.2019; us patent application 16/373,206 published as us patent application publication 2019/0223481 on 25.7.2019; and us patent application 16/374,422 published as us patent application publication 2019/0223483 at 25.7.2019, each of which is incorporated herein by reference in its entirety.

In some aspects, the amount of sensory modifier effective to reduce lingering sweet aftertaste may be an amount effective to reduce the lingering sweet aftertaste score by at least 1 unit, wherein the lingering sweet aftertaste score is determined by at least four panelists trained in tasting steviol glycoside solutions using a round table method using a scale of 0 to 6, wherein a score of 0 indicates lingering sweet aftertaste and a score of 6 indicates lingering extreme sweet aftertaste. In other aspects, an amount effective to reduce lingering sweet aftertaste comprises an amount effective to reduce the lingering sweet aftertaste score by at least 1 unit, 2 units, 3 units, 4 units, 5 units, or 6 units. In other aspects, an amount effective to reduce lingering sweet aftertaste comprises an amount effective to reduce the lingering sweet aftertaste score to less than 5, 4, 3,2, or 1 units. In some aspects, an amount effective to reduce lingering sweet aftertaste comprises an amount effective to reduce the lingering sweet aftertaste score to zero.

The composition may have various amounts of sensory modifiers. The sensory modifier may be present in the composition in any amount required for a particular use. For example, the sensory modifier may be present in the composition at a total concentration of about 1ppm to about 1000ppm or about 1ppm to about 2000 ppm. In some aspects, the sensory modifier may be present in the composition at a total concentration of about 100ppm to about 2000ppm, about 200ppm to about 2000ppm, 300ppm to about 2000ppm, 400ppm to about 2000ppm, 500ppm to about 2000ppm, 600ppm to about 2000ppm, 700ppm to about 2000ppm, 800ppm to about 2000ppm, 900ppm to about 2000ppm, or 1000ppm to about 2000 ppm. In some aspects, the sensory modifier can be present in the composition in a total concentration equal to or greater than about 10ppm, 100ppm, 200ppm, 300ppm, 400ppm, 500ppm, 600ppm, 700ppm, 800ppm, 900ppm, 1000ppm, 110ppm, 1200ppm, 1300ppm, 1400ppm, 1500ppm, 1600ppm, 1700ppm, 1800ppm, 1900ppm, or 2000 ppm. In various aspects, the sensory modifier may be present in the composition at a total concentration of about 100ppm to about 1000ppm, about 200ppm to about 1000ppm, 300ppm to about 1000ppm, 400ppm to about 1000ppm, 500ppm to about 1000ppm, 600ppm to about 1000ppm, 700ppm to about 1000ppm, 800ppm to about 1000ppm, or 900ppm to about 1000 ppm. In some aspects, the sensory modifier may be present in the composition at a total concentration of about 100ppm to about 800ppm, about 200ppm to about 800ppm, 300ppm to about 800ppm, 400ppm to about 800ppm, 500ppm to about 800ppm, 600ppm to about 800ppm, or 700ppm to about 800 ppm. In some aspects, the sensory modifier can be present in the composition at a total concentration of about 400ppm to about 800 ppm.

The amount of the individual sensory modifier materials in the various compositions described herein can each independently vary. For example, monocaffeoylquinic acid, dicaffeoylquinic acid, or both, may each be present in the composition individually at a concentration of from about 1ppm to about 1000 ppm. In some aspects, monocaffeoylquinic acid, dicaffeoylquinic acid, or both, may each be present individually at a concentration of from about 100ppm to about 1000ppm, from about 200ppm to about 1000ppm, from 300ppm to about 1000ppm, from 400ppm to about 1000ppm, from 500ppm to about 1000ppm, from 600ppm to about 1000ppm, from 700ppm to about 1000ppm, from 800ppm to about 1000ppm, from 900ppm to about 1000 ppm. In some aspects, monocaffeoylquinic acid, dicaffeoylquinic acid, or both, may each be present individually at a concentration equal to or greater than about 10ppm, 50ppm, 100ppm, 200ppm, 300ppm, 400ppm, 500ppm, 600ppm, 700ppm, 800ppm, 900ppm, or 1000 ppm. In some aspects, monocaffeoylquinic acid, dicaffeoylquinic acid, or both, may each be present in the composition individually at a concentration of from about 100ppm to about 800ppm, from about 200ppm to about 800ppm, from 300ppm to about 800ppm, from 400ppm to about 800ppm, from 500ppm to about 800ppm, from 600ppm to about 800ppm, or from 700ppm to about 800 ppm. In some aspects, the monocaffeoylquinic acid, dicaffeoylquinic acid, or both, may each be present in the composition individually at a concentration of from about 400ppm to about 800 ppm.

Plant source of sensory modifier

In various embodiments, the sensory modifier can be isolated from a plant source. The plurality of plant sources comprises the sensory modifier, and the sensory modifier can be isolated from these plant sources. Some examples of plant sources from which the sensory modifier may be isolated include eucommia ulmoides (eucommia ulmoides), honeysuckle, nicotiana benthamiana (nicotiana benthamiana), artichoke, stevia rebaudiana (stevia rebaudiana), luo han guo, coffee bean, green coffee bean, tea, white tea, yellow tea, green tea, oolong tea, black tea, rooibos tea, post-fermented tea, bamboo, southeast stonecrop, sunflower, blueberry cranberry, cowberry (bilberry), currant, vaccinium myrtillus (vaccinberry), vaccinium myrtillus (lingonberry), cowberry (cowberry), american cowberry (huckleberry), grape, chicory, echinacea orientalis (eastern purple coneflower), echinacea (echinacea), european parvietwork, pellith, agrimony (Common ivory), Common sage (Common nettle), Common nettle (Common leaf), Common nettle (Common nettle), Common nettle, Common root, Common potato (Common root, Common leaf, solanum torvum (Aubergine), Lycopersicum esculentum, cherry tomato, bitter apple, stramonium, sweet potato, apple, peach, nectarine, cherry, tart cherry, malpighia glabra, apricot, almond, plum, dried plum, ilex purpurea, Mate tea (Mate), Guashua tea, ilex latifolia, guarana, cacao bean, kola, cola, kola, ostrich, Eastern ostrich, bracken, lupinus, oriental ostrich, Asian royal fern, royal purple osmunda, European fern, phoenix-tail, common fern, Eastern brakenefem, clove, cinnamon, Indian bay leaf, nutmeg, bay leaf, basil, sage (Great basil), sage, jojobstearin, sage, rosemary, sage, and rosemary, Wild marjoram, sweet marjoram, multi-noded marjoram, potted marjoram, dill, anise, star anise, fennel, anise, sweet wormwood (Tarragon), Tarragon (Estragon), mugwort, licorice, soy (Soybean), soy (Soyabean), Soya vean, wheat, common wheat, rice, rapeseed, broccoli, cauliflower, cabbage, kale, cabbage, brussels sprouts, linxian bark, elderberry, chamomile, burdock, valerian, and chamomile.

Some plant sources can produce sensory modifiers that are rich in one or more of caffeic acid, monocaffeoylquinic acid, and dicaffeoylquinic acid. For example, sensory modifiers isolated from the yerba mate plant (Ilex paraguariensis) are rich in mono-and dicaffeoylquinic acids. In other aspects, the dicaffeoylquinic acid-rich sensory modifier isolated from mate tea plants may comprise 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more or 50% or more, 60% or more, 70% or more or 80% or more or 90% or more of 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, and 4, 5-dicaffeoylquinic acid, and combinations of one or more of their salts. For example, sensory modifiers isolated from other plant sources may be enriched in dicaffeoylquinic acid. In other aspects, the dicaffeoylquinic acid-rich sensory modifier isolated from other plant sources may comprise 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more or 50% or more, 60% or more, 70% or more or 80% or more or 90% or more of 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, and 4, 5-dicaffeoylquinic acid, and combinations of one or more of their salts.

The sensory modifier can be isolated in a variety of ways. Some suitable methods are disclosed in more detail in the following patent applications: us patent application 16/373,206 entitled "stevia sugar solublities Enhancers" filed 4.4.2019, which was published as us patent application publication 2019/0223481 25.7.2019; international application PCT/US2018/054691 entitled "stevia sugar solublities Enhancers" filed on 5.10.2018; us provisional application 62/569,279 entitled "stevia sugar solublities Enhancers" filed on 6.10.2017; us patent application 16/374,894 entitled "Methods for Making yuba Mate Composition" filed 4/2019, which was published as us patent application publication 2019/0231834 8/1/2019; international application PCT/US2018/054688 entitled "Methods for Making Yerba Mate Composition", filed on 5.10.2018; and filed 5 months and 25 days 2018 under the name of "Methods for Making YU.S. provisional application serial No. 62/676,722 to erbb Mate Extract Composition ". For example, the sensory modifier can be isolated from a plant source and comprise one or more of monocaffeoylquinic acid, dicaffeoylquinic acid, and salts thereof. For example, yerba mate biomass and stevia biomass can be used to prepare sensory modifiers. In one exemplary process, the sensory modifier is prepared from commercially available comminuted mate tea biomass. Briefly, mate tea biomass was suspended in 50% (v/v) ethanol/water, shaken for at least 1 hour, and the resulting mixture was filtered to obtain the initial extract. The initial extract was diluted with 35% (v/v) ethanol/water and filtered again. The re-filtered permeate was then applied to a solution which had been equilibrated in 35% (v/v) ethanol/waterThe FPA 53 resin column and the column permeate was discarded. The column was washed with 35% (v/v) ethanol/water and the column permeate was discarded. The column was then eluted with 10% (w/v) FCC grade sodium chloride in 50% (v/v) ethanol/water and the eluate was retained. Nitrogen was blown over the surface of the eluent at room temperature to remove the ethanol and reduce the eluent to 1/3 of its original volume. The volume-reduced eluate was then filtered through a 0.2 μm polyethersulfone filter and then decolorized by passing it through a 3kDa molecular weight cut-off membrane. The decolorized permeate is retained and desalted by passing it through a nanofiltration membrane. The desalted permeate was then freeze-dried to obtain the sensory modifier. The method is also applicable to obtaining sensory modifiers from stevia biomass, and may be applicable to obtaining sensory modifiers from other plant sources, such as those described above.

In some aspects, the sensory modifier can be a blend of sensory modifiers isolated from more than one plant source.

In some aspects, the compositions with steviol glycosides and sensory modifiers do not include above a particular cut-off weight% of certain compounds. For example, the composition may comprise less than 0.3% by weight of malonate, malonic acid, oxalate, oxalic acid, lactate, lactic acid, succinate, succinic acid, malate, or malic acid; or less than 0.05% by weight of pyruvate, pyruvic acid, fumarate, fumaric acid, tartrate, tartaric acid, sorbate, sorbic acid, acetate or acetic acid; or less than about 0.05 wt% chlorophyll.

Composition comprising a metal oxide and a metal oxide

The steviol glycosides, along with one or more sensory modifiers, can be incorporated into any known edible material (referred to herein as "sweetenable compositions") or other composition intended for ingestion by and/or contact with the mouth of a human or animal, such as, for example, pharmaceutical compositions, edible gel mixes and compositions, dental and oral hygiene compositions, foodstuffs (e.g., candies, condiments, chewing gums, cereal compositions, baked goods, culinary aids, dairy products, and tabletop sweetener compositions), beverages, and other beverage products (e.g., beverage mixes, beverage concentrates, and the like). Examples of such compositions and aspects thereof are shown in PCT international publications WO 2019/071220 and WO 2019/071182 and in U.S. patent application publications 2019/0223481 and 2019/0223483, each of which is incorporated herein by reference in its entirety.

Pharmaceutical compositions comprise a pharmaceutically active substance and a pharmaceutically acceptable carrier or excipient material. The dental composition comprises an active dental substance that improves the aesthetic or health status of at least a portion of the oral cavity and a base material that is an inactive substance that acts as a vehicle.

The steviol glycoside composition may be a tabletop sweetener composition. The tabletop sweetener compositions can also comprise a variety of other ingredients, such as one or more bulking agents, additives, anti-caking agents, functional ingredients, or any combination thereof. Suitable "bulking agents" include, but are not limited to, maltodextrin (10DE, 18DE or 5DE), corn syrup solids (20DE or 36DE), sucrose, fructose, glucose, invert sugar, sorbitol, xylose, ribulose, mannose, xylitol, mannitol, galactitol, erythritol, maltitol, lactitol, isomalt, maltose, tagatose, lactose, inulin, glycerol, propylene glycol, polyols, polydextrose, fructooligosaccharides, cellulose and cellulose derivatives, and the like, and mixtures thereof. In addition, according to other aspects, granulated sugar (sucrose) or other caloric sweeteners, such as crystalline fructose, other carbohydrates, or sugar alcohols, can be used as bulking agents because they provide good content uniformity without adding significant calories. The tabletop sweetener compositions can also be presented in liquid form, wherein the sweetener composition comprising a steviol glycoside component and comprising one or more organoleptic modifiers is combined with a liquid carrier. Non-limiting examples of carrier agents suitable for use in a liquid table functional sweetener include water, alcohols, polyols, glycerin or citric acid matrices dissolved in water, and mixtures thereof. Additional aspects of table sweeteners are shown in PCT international publications WO 2019/071220 and WO 2019/071182 and in U.S. patent application publications 2019/0223481 and 2019/0223483, each of which is incorporated herein by reference in its entirety.

The steviol glycoside composition may be a beverage. As used herein, "beverage product" includes, but is not limited to, a ready-to-drink beverage, beverage concentrate, beverage syrup, frozen beverage, or powdered beverage. Suitable ready-to-drink beverages include carbonated beverages and non-carbonated beverages. Carbonated beverages include, but are not limited to, fortified carbonated waters, colas, orange-flavored carbonated waters, grape-flavored carbonated waters, strawberry-flavored carbonated waters, pineapple-flavored carbonated waters, ginger-flavored beverages, soft drinks, and wheatroot sauries. Non-carbonated beverages include, but are not limited to, fruit juices, fruit flavored juices, fruit juice drinks, nectars, vegetable juices, vegetable flavored juices, sport drinks, energy drinks, energized water drinks, vitamin energized water, near water drinks (e.g., water with natural or synthetic flavors), coconut water, tea beverages (e.g., black tea, green tea, rooibos tea, oolong tea), coffee, cocoa drinks, beverages containing milk ingredients (e.g., milk drinks, coffee containing milk ingredients, cappuccino, milk tea, fruit milk drinks), beverages containing grain extracts, smoothies, and combinations thereof. Examples of frozen beverages include, but are not limited to, shaved ice, frozen cocktails, gehri, sorbet, margarita, milkshakes, frozen coffee, frozen lemonade, granita, and slush (slushes). Beverage concentrates and beverage syrups can be prepared with an initial volume of liquid base (e.g., water) and the desired beverage ingredients. A full strength beverage is then prepared by adding an additional volume of water. Powdered beverages are prepared by dry mixing all beverage ingredients in the absence of a liquid base. A full strength beverage is then prepared by adding the entire volume of water.

In one embodiment, the beverage contains a sweetener composition comprising a steviol glycoside component and an organoleptic modifier. Any sweetener composition comprising a steviol glycoside and an organoleptic modifier as detailed herein can be used in the beverage. In another embodiment, a method of making a beverage includes combining a liquid base, a steviol glycoside component and an organoleptic modifier. The method may further comprise adding one or more sweeteners, additives and/or functional ingredients. In yet another embodiment, a method of making a beverage includes combining a liquid base and a sweetener composition comprising a steviol glycoside component and an organoleptic modifier.

In another embodiment, the beverage contains a sweetener composition containing steviol glycosides, where the steviol glycosides are present in the beverage in an amount in the range of from about 1ppm to about 10,000ppm (such as, for example, from about 25ppm to about 800 ppm). In another embodiment, the steviol glycosides are present in the beverage in an amount in the range of about 100ppm to about 600 ppm. In other aspects, the steviol glycosides are present in the beverage in an amount in the range of about 100ppm to about 200ppm, about 100ppm to about 300ppm, about 100ppm to about 400ppm, or about 100ppm to about 500 ppm. In yet another embodiment, the steviol glycosides are present in the beverage in an amount in the range of from about 300ppm to about 700ppm, such as for example from about 400ppm to about 600 ppm. In a particular embodiment, the steviol glycosides are present in the beverage in an amount of about 500 ppm.

In one embodiment, the composition is a beverage and the total glycoside content in the beverage is about 50ppm to 1500ppm or 100ppm to 1200ppm, 200ppm to 1000ppm, 300ppm to 900ppm, 350ppm to 800ppm, 400ppm to 600ppm or 450ppm to 550 ppm. In one embodiment, steviol glycosides (e.g., sensory modifiers) other than Reb D, Reb M, Reb B, and/or Reb a, or other than Reb D and/or Reb B, and optionally other than Reb G, Reb O, Reb N, and/or Reb E, are present in the beverage in an amount of about at least 1ppm to about 600ppm (e.g., about 50ppm to about 500ppm, including at least 1ppm, 5ppm, 10ppm, 20ppm, 30ppm, 40ppm, 50ppm, 125ppm, 150ppm, 175ppm, or 200 ppm). In one embodiment, steviol glycosides other than Reb D, Reb M, Reb B, and/or Reb a, or other than Reb D and/or Reb B, and optionally other than Reb G, Reb O, Reb N, and/or Reb E, are present in the beverage at about 1ppm to 600ppm, 10ppm to 400ppm, 50ppm to 200ppm, 75ppm to 150ppm, 5ppm to 200ppm, 10ppm to 100ppm, 20ppm to 90ppm, 30ppm to 80ppm, and so forth. In one embodiment, steviol glycosides other than Reb D, Reb M, Reb B, and/or Reb a are present in the beverage at about 1ppm to 600ppm, 10ppm to 400ppm, 50ppm to 200ppm, 75ppm to 150ppm, 5ppm to 200ppm, 10ppm to 100ppm, 20ppm to 90ppm, 30ppm to 80ppm, and so on.

Additional Components

In some aspects, the compositions having a steviol glycoside component and an organoleptic modifier also contain one or more additional non-steviol glycoside sweetener compounds. The non-steviol glycoside sweetener compound may be any type of sweetener, for example, a sweetener obtained from a plant or plant product or a physically or chemically modified sweetener obtained from a plant or a synthetic sweetener. Exemplary non-steviol glycoside sweeteners include sucrose, fructose, glucose, erythritol, maltitol, lactitol, sorbitol, mannitol, xylitol, tagatose, trehalose, galactose, rhamnose, cyclodextrins (e.g., alpha-cyclodextrin, beta-cyclodextrin, and gamma-cyclodextrin), ribulose, threose, arabinose, xylose, lyxose, allose, altrose, mannose, idose, lactose, maltose, invert sugar, isohexide, neotrehalose, palatinose, or isomaltulose, erythrose, deoxyribose, gulose, idose, talose, erythrulose, xylulose, psicose, turanose, cellobiose, glucosamine, mannosamine, fucose, fucoidan, glucuronic acid, gluconic acid, gluconolactone, abicortole, galactosamine, xylooligosaccharides (xylotriose, xylooligosaccharide, xylotriose, and beta-cyclodextrin, Xylobiose, etc.), gentiooligosaccharides (gentiobiose, gentiotriose, gentiotetraose, etc.), galactooligosaccharides, sorbose, ketotriose (dihydroxyacetone), aldotriose (glyceraldehyde), nigerooligosaccharide, fructooligosaccharides (kestose, nystotetraose, etc.), maltotetraose, maltotrioitol, tetrasaccharides, oligomannose, maltotriose (maltotriose, maltotetraose, maltopentaose, maltohexaose, maltoheptaose, etc.), dextrin, lactulose, melibiose, raffinose, rhamnose, ribose, sucralose, isomerized liquid sugars such as high fructose corn/starch syrup (HFCS/HFSS) (e.g., HFCS55, HFCS42, or HFCS90), conjugated sugars, soy oligosaccharides, glucose syrups, and combinations thereof. When applicable, either the D-configuration or the L-configuration may be used. Non-steviol glycoside sweeteners and aspects thereof are also described in PCT international publications WO 2019/071220 and WO 2019/071182 and in U.S. patent application publications 2019/0223481 and 2019/0223483, each of which is incorporated herein by reference in its entirety.

In various embodiments, the steviol glycoside compositions may also optionally comprise a liquid carrier, a binder matrix, additional additives, or the like. In some aspects, the sweetener composition contains additives including, but not limited to, carbohydrates, polyols, amino acids and their corresponding salts, polyamino acids and their corresponding salts, sugar acids and their corresponding salts, nucleotides, organic acids, inorganic acids, organic salts (including organic acid salts and organic base salts), inorganic salts, bitter compounds, flavoring and flavor ingredients, astringent compounds, proteins or protein hydrolysates, surfactants, emulsifiers, weighting agents, gums, antioxidants, colorants, flavonoids, alcohols, polymers, and combinations thereof. In some aspects, the additives are used to improve the temporal and flavor characteristics of the sweetener to provide a favorable taste to the sweetener composition, such as a sucrose-like taste. Examples of such ingredients and aspects thereof are shown in PCT international publications WO 2019/071220 and WO 2019/071182 and in U.S. patent application publications 2019/0223481 and 2019/0223483, each of which is incorporated herein by reference in its entirety.

Sweetener compositions comprising a steviol glycoside component and an organoleptic modifier may also contain one or more functional ingredients that provide a real or perceived health benefit to the composition. Functional ingredients include, but are not limited to, saponins, antioxidants, dietary fiber sources, fatty acids, vitamins, glucosamine, minerals, preservatives, hydrating agents, probiotics, prebiotics, weight control agents, osteoporosis control agents, phytoestrogens, long chain primary aliphatic saturated alcohols, phytosterols, and combinations thereof. Examples of functional ingredients and aspects thereof are shown in PCT international publications WO 2019/071220 and WO 2019/071182 and in U.S. patent application publications 2019/0223481 and 2019/0223483, each of which is incorporated herein by reference in its entirety.

The invention may be better understood by reference to the following examples which are provided by way of illustration. The present invention is not limited to the embodiments given herein.

Examples

Materials and methods

Various steviol glycoside components were tested.

The sensory modifiers tested were a mixture of monocaffeoylquinic acid and dicaffeoylquinic acid prepared from mate tea, and subsequently adjusted to have various salt fractions. Table 2 lists the content and source of the various components.

Solutions containing the steviol glycoside component alone (used as a control sample) or the steviol glycoside component and sensory modifier (in a molar ratio of 2: 1, which also corresponds to a weight ratio of 2: 1) were prepared. Solutions were prepared by dissolving the steviol glycoside component and sensory modifier into reverse osmosis water at the specified concentrations and/or ratios.

Table 2.

Assays were performed to characterize the sensory attributes of the steviol glycoside compositions with various salt fractions of sensory modifiers. The organoleptic properties of the solutions were tested by a panel of at least four individuals experienced in tasting steviol glycoside compositions. An experienced panelist used the round table method to evaluate each sweetness profile. To test each solution, an experienced panelist dispensed approximately 2mL of each solution into their mouth by pipette, dispensed the solution by moving the tongue, and recorded the value of the particular sweetness profile tested. Between tastings of different solutions, panelists were able to cleanse the taste with water. For each sweetness attribute, the panelists agreed on a descriptive scale of the relative intensity assigned to each sweetness attribute, and then recorded the value of each sweetness attribute against that descriptive scale. Table 3 lists the scoring criteria for various sensory attributes.

Table 3.

Example 1 aqueous test sample

A mixture of monocaffeoylquinic acid and dicaffeoylquinic acid is obtained from mate tea to provide the sensory modifier in acid form. The mixture of monocaffeoylquinic acid and dicaffeoylquinic acid is adjusted with sodium hydroxide or potassium hydroxide, independently of the steviol glycoside component, to obtain sodium or potassium salts (each corresponding to 100% salt form). The resulting samples were freeze dried to provide the Sensory Modifier (SM) in the form of a ready-to-use powder. A series of samples were prepared from the sensory modifier. The final concentration of sensory modifier was 470ppm to 500ppm (weight/weight) for each sample, including the contribution of salt mass. The preparation of each sample including the amount of each ingredient is shown in tables 4-6. Steviol glycoside components examples a and B were used alone as control samples and also as starting points for sensory modified samples.

Table 4.

Table 5.

Table 6.

For each sample, its flavor profile was compared to the steviol glycoside solution alone and to samples with different salt compositions.

Both the potassium and sodium salt forms of the sensory modifier showed an improvement over Reb M alone. Table 7 shows the reported sensory attributes for each of the tested compositions. Table 8 shows the reported SEV values for each of the tested compositions and provides a review of the tasters. As shown in table 7, for Reb M, the potassium salt form and the sodium salt form resulted in a substantially more rounded sweetness profile. For both Reb M and Reb N, the potassium salt form and the sodium salt form result in a substantially reduced duration of sweet aftertaste and a greatly reduced bitterness. As shown in table 8, the potassium salt form and the sodium salt form resulted in slightly reduced SEV. The potassium salt imparts slightly more astringency than the sodium salt form of the total sensory modifier. There was a light cherry fruit flavor introduced with the potassium salt. Thus, it was shown that the sodium salt form and the potassium salt form of the sensory modifier resulted in a significant modulation of the sensory characteristics of the steviol glycoside component. In view of the number of various sensory attributes that can each be varied independently, it is surprising that the sensory modifier in salt form provided the desired results in each test and overall without significant drawbacks in any one regard. Furthermore, a very significant improvement in bitterness reduction and a sustained reduction in sweet aftertaste was shown compared to the samples lacking the sensory modifier.

Table 7.

Typical Reb M and Reb N attributes are astringency, metallic flavor, powder sensation, numbing sensation, vapor sensation

ND is not detected

Table 8.

Example 2-simulated beverage testing

Simulated beverages were prepared using a steviol glycoside component, an organoleptic modifier, and a simulated beverage system.

To prepare a simulated beverage system, citric acid (anhydrous, final concentration 0.1 wt%) and potassium citrate (monohydrate, final concentration 0.026 wt%) were dissolved in deionized water. To this buffer system was added the steviol glycoside component example C in order to give a final concentration of 350ppm (weight/weight) and allowed to dissolve. Steviol glycoside component embodiment C comprises rebaudiosides M and D.

A mixture of monocaffeoylquinic acid and dicaffeoylquinic acid in acid form (i.e., at 100 mole% acid fraction) was treated with sodium hydroxide to introduce salt fractions and adjust the salt mole% fractions to various mole fractions as shown in table 9. Thus, the resulting caffeoylquinic acid mixture contains monocaffeoylquinic acid in acid form, dicaffeoylquinic acid in acid form, monocaffeoylquinic acid in salt form, and dicaffeoylquinic acid in salt form. The resulting mixture was freeze-dried to provide several ready-to-use sensory modifiers in powder form. These sensory modifiers are described in table 9 in terms of mole% of sodium (which is equivalent to the salt fraction in this example). Due to the similarity in molecular weight between the acid and salt forms, the mole% of Na can be interpreted as approximately equal to the weight%.

Next, a series of test beverages were prepared by combining the beverage system described above with a sensory modifier. For each of the resulting simulated beverage samples, the final concentration of sensory modifier was 250ppm (weight/weight) and was adjusted based on the total mass of sensory modifier (not including the contribution of salt mass). For each sample, its flavor profile was compared to the steviol glycoside solution alone and to samples with different salt fractions. After tasting each sample, the panelists voted based on personal preference as to which salt score provided better sweetness profile.

As shown in the table, to some extent, individuals prefer all samples in the 50 mole% to 80 mole% salt fraction range, with the optimal composition being 70 mole%. At high salt levels (80 mol% salt to 100 mol% salt), the product is not effective in reducing the lingering sweet aftertaste of Reb M and has an unpleasant musty, earthy taste. Products with salt contents between 60 and 80 mole% are very effective in reducing the lingering sweet aftertaste and reducing the bitterness of Reb M, and have an unpleasant musty taste diminished. At a salt content of 70 mol%, the musty taste is very mild, and the sweetness is preceded with a pure and rounded taste profile, and the sweet aftertaste is continuously reduced. At a salt content of less than 60 mole%, the astringency, together with tongue coating and tingling, becomes more and more prominent.

The data show that a particular range of salt fractions (salt mole%) of the sensory modifier provides significantly reduced bitterness and significantly reduced lingering sweet aftertaste. This result is particularly surprising as it cannot be predicted by looking at the acid form alone or the salt form alone. For example, the acid form alone (0 mole% salt) results in undesirable sour and astringent tastes. The salt form alone (100 mole% salt) provided similar results as the case without any organoleptic modifiers at all. Neither the acid form alone nor the salt form alone provides any significant reduction in bitterness or sustained sweetness linger. Thus, it is surprising that the combination of acid and salt introduces the sustained beneficial effect of reduced bitterness and reduced sweet aftertaste. It is also surprising that this advantage is not achieved in all cases where both salt and acid are present, for example, mixtures with a salt content of less than 50 mole% do not provide the same advantage, and mixtures with a salt content above 90 mole% begin to provide only a slightly reduced lingering sweet aftertaste.

TABLE 9 influence of salt number on sensory attributes and preferences

Exemplary embodiments

The present disclosure provides the following embodiments, the numbering of which should not be construed as specifying the level of importance:

embodiment 1 relates to a steviol glycoside composition comprising:

a steviol glycoside component; and

a sensory modifier in an amount effective to reduce lingering sweet aftertaste, reduce bitterness, or both,

wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the salt form.

Embodiment 2 relates to a steviol glycoside composition with reduced lingering of sweet aftertaste, which composition comprises:

a steviol glycoside component; and

a sensory modifier in an amount effective to reduce lingering sweet aftertaste, reduce bitterness, or both,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid, and

wherein the salt fraction comprises at least 50 wt% of the total sensory modifier.

Embodiment 3 relates to the steviol glycoside composition of embodiments 1 or 2, wherein the sensory modifier comprises one or more of: chlorogenic acid (5-O-caffeoyl quinic acid), neochlorogenic acid (3-O-caffeoyl quinic acid), cryptochlorogenic acid (4-O-caffeoyl quinic acid), 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid or 4, 5-dicaffeoylquinic acid and their salts.

Embodiment 4 relates to a steviol glycoside composition according to any one of embodiments 1 to 3, wherein the sensory modifier is a mixture of one or more monocaffeoylquinic acids, one or more dicaffeoylquinic acids, and salts thereof.

Embodiment 5 relates to a steviol glycoside composition of any one of embodiments 2 to 4, wherein the monocaffeoylquinic acid is one or more of chlorogenic acid (5-O-caffeoylquinic acid), neochlorogenic acid (3-O-caffeoylquinic acid), or cryptochlorogenic acid (4-O-caffeoylquinic acid).

Embodiment 6 relates to a steviol glycoside composition of any one of embodiments 2 to 5, wherein monocaffeoylquinic acid salt is one or more of a salt of 3-O-caffeoylquinic acid, a salt of 4-O-caffeoylquinic acid, or a salt of 5-O-caffeoylquinic acid.

Embodiment 7 relates to a steviol glycoside composition of any one of embodiments 2 to 5, wherein dicaffeoylquinic acid salt is one or more of a salt of 1, 3-dicaffeoylquinic acid, a salt of 1, 4-dicaffeoylquinic acid, a salt of 1, 5-dicaffeoylquinic acid, a salt of 3, 4-dicaffeoylquinic acid, a salt of 3, 5-dicaffeoylquinic acid, or a salt of 4, 5-dicaffeoylquinic acid.

Embodiment 8 relates to a steviol glycoside composition of any one of embodiments 2 to 5, wherein dicaffeoylquinic acid is one or more of 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, or 4, 5-dicaffeoylquinic acid.

Embodiment 9 relates to the steviol glycoside composition of any one of embodiments 1 to 8, wherein 10% or more by weight of the sensory modifier is dicaffeoylquinic acid and salts thereof.

Embodiment 10 relates to steviol glycoside compositions according to any one of embodiments 1 to 9, wherein 25% or more by weight of the sensory modifier is dicaffeoylquinic acid and salts thereof.

Embodiment 11 relates to the steviol glycoside composition of any one of embodiments 1 to 10, wherein 50% or more by weight of the sensory modifier is dicaffeoylquinic acid and salts thereof.

Embodiment 12 relates to a steviol glycoside composition according to any one of embodiments 1 to 11, wherein the sensory modifier is a mixture of monocaffeoylquinic acid and salts of monocaffeoylquinic acid: dicaffeoylquinic acid and salts of dicaffeoylquinic acid in a ratio of from 3: 1 to 1: 3.

Embodiment 13 relates to a steviol glycoside composition of any one of embodiments 1 to 12, wherein the ratio of monocaffeoylquinic acid and salts of monocaffeoylquinic acid to salts of dicaffeoylquinic acid and dicaffeoylquinic acid of the sensory modifier is about 1: 1.

Embodiment 14 relates to a steviol glycoside composition of any one of embodiments 1 to 13, wherein the sensory modifier is a mixture of dicaffeoylquinic acid and salts thereof from 40 to 60% by weight.

Embodiment 15 relates to the steviol glycoside composition of any one of embodiments 1 to 14, wherein 90% or less by weight of the sensory modifier is in salt form.

Embodiment 16 relates to the steviol glycoside composition of any one of embodiments 1 to 15, wherein 80% or less by weight of the sensory modifier is in the form of a salt.

Embodiment 17 relates to the steviol glycoside composition of any one of embodiments 1 to 16, wherein 50 to 90% by weight of the sensory modifier is in salt form.

Embodiment 18 relates to the steviol glycoside composition of any one of embodiments 1 to 17, wherein 60 to 80% by weight of the sensory modifier is in salt form.

Embodiment 19 relates to the steviol glycoside composition of any one of embodiments 1 to 18, wherein 65 to 75 wt.% of the sensory modifier is in salt form.

Embodiment 20 relates to the steviol glycoside composition of any one of embodiments 1 to 19, wherein at least 10% by weight of the sensory modifier is in the acid form.

Embodiment 21 relates to the steviol glycoside composition of any one of embodiments 1 to 20, wherein at least 20% by weight of the sensory modifier is in the acid form.

Embodiment 22 relates to the steviol glycoside composition of any one of embodiments 1 to 21, wherein 20 to 40 wt.% of the sensory modifier is in acid form.

Embodiment 23 relates to the steviol glycoside composition of any one of embodiments 1 to 22, wherein 25 to 35% by weight of the sensory modifier is in the acid form.

Embodiment 24 relates to the steviol glycoside composition of any one of embodiments 2 to 23, wherein the salt fraction comprises at least 60 wt.% of the total sensory modifier.

Embodiment 25 relates to the steviol glycoside composition of any one of embodiments 2 to 23, wherein the salt fraction comprises less than 90 wt.% of the total sensory modifier.

Embodiment 26 relates to the steviol glycoside composition of any one of embodiments 2 to 23, wherein the salt fraction comprises less than 80 wt.% of the total sensory modifier.

Embodiment 27 relates to the steviol glycoside composition of any one of embodiments 2 to 23, wherein the salt fraction comprises from 60 to 80 wt.% of the total sensory modifier.

Embodiment 28 relates to the steviol glycoside composition of any one of embodiments 2 to 23, wherein the salt fraction comprises from 65 to 75 weight% of the total sensory modifier.

Embodiment 29 relates to the steviol glycoside composition of any one of embodiments 2 to 28, wherein the acid fraction comprises at least 10 wt.% of the total sensory modifier.

Embodiment 30 relates to the steviol glycoside composition of any one of embodiments 2 to 29, wherein the acid fraction comprises at least 20 wt.% of the total sensory modifier.

Embodiment 31 relates to the steviol glycoside composition of any one of embodiments 2 to 30, wherein the acid fraction comprises from 20 to 40 weight% of the total sensory modifier.

Embodiment 32 relates to the steviol glycoside composition of any one of embodiments 2 to 31, wherein the acid fraction comprises from 25 to 35 weight% of the total sensory modifier.

Embodiment 33 relates to the steviol glycoside composition of any one of embodiments 1 to 32, wherein the sensory modifier comprises one or more salts selected from sodium, potassium, magnesium and calcium.

Embodiment 34 relates to the steviol glycoside composition of any one of embodiments 1 to 33, wherein the sensory modifier comprises one or more sodium salts.

Embodiment 35 relates to the steviol glycoside composition of any one of embodiments 1 to 34, wherein the sensory modifier comprises one or more potassium salts.

Embodiment 36 relates to the steviol glycoside composition of any one of embodiments 1 to 35, wherein the sensory modifier comprises a mixture of one or more potassium salts and one or more sodium salts.

Embodiment 37 relates to the steviol glycoside composition of any one of embodiments 1 to 36, wherein the pH of the composition is greater than the pH at the half-equivalence point of the sensory modifier.

Embodiment 38 relates to the steviol glycoside composition of any one of embodiments 1 to 37, wherein the pH of the composition is less than the pH at the equivalence point of the sensory modifier.

Embodiment 39 relates to the steviol glycoside composition of any one of embodiments 1 to 38, wherein the pH of the composition is less than 4.0.

Embodiment 40 relates to the steviol glycoside composition of any one of embodiments 1 to 39, wherein the pH of the composition is from 1.7 to 4.0.

Embodiment 41 relates to a steviol glycoside composition according to any one of embodiments 1 to 40, wherein the pH of the composition is greater than 2.0.

Embodiment 42 relates to a steviol glycoside composition according to any one of embodiments 1 to 41, wherein the pH of the composition is greater than 2.5.

Embodiment 43 relates to the steviol glycoside composition of any one of embodiments 1 to 42, wherein at least a portion of the sensory modifier is prepared from a botanical source.

Embodiment 44 relates to the steviol glycoside composition of any one of embodiments 1 to 43, wherein the plant source is mate tea, rosemary, chicory, stevia, artichoke, coffee or a mixture thereof.

Embodiment 45 relates to the steviol glycoside composition of any one of embodiments 1 to 44, wherein at least a portion of the sensory modifier is prepared from mate tea.

Embodiment 46 relates to the steviol glycoside composition of any one of embodiments 1 to 45, wherein at least a portion of the sensory modifier is prepared from stevia.

Embodiment 47 relates to the steviol glycoside composition of any one of embodiments 1 to 46, wherein the steviol glycoside component comprises one or more of rebaudioside D, rebaudioside M, rebaudioside O, rebaudioside N, rebaudioside A or a combination thereof.

Embodiment 48 relates to the steviol glycoside composition of any one of embodiments 1 to 47, wherein the steviol glycoside component comprises rebaudioside D, rebaudioside M or a combination thereof.

Embodiment 49 relates to the steviol glycoside composition of any one of embodiments 1 to 48, wherein at least 80% by weight of the steviol glycoside component is rebaudioside M, based on the total weight of steviol glycosides in the steviol glycoside composition.

Embodiment 50 relates to the steviol glycoside composition of any one of embodiments 1 to 49, wherein at least 90% by weight of the steviol glycoside component in the steviol glycoside composition is rebaudioside M.

Embodiment 51 is directed to the steviol glycoside composition of any one of embodiments 1 to 50, wherein the composition comprises from 100ppm to 1600ppm steviol glycosides.

Embodiment 52 relates to the steviol glycoside composition of any one of embodiments 1 to 51, wherein the composition comprises at least 200ppm of the steviol glycoside component.

Embodiment 53 relates to a steviol glycoside composition according to any one of embodiments 1 to 52, wherein composition comprises from 200ppm to 1000ppm of the steviol glycoside component.

Embodiment 54 relates to the steviol glycoside composition of any one of embodiments 1 to 53, wherein the composition comprises at least 300ppm of the steviol glycoside component.

Embodiment 55 relates to the steviol glycoside composition of any one of embodiments 1 to 54, wherein the composition comprises from 400ppm to 800ppm of the steviol glycoside component.

Embodiment 56 relates to the steviol glycoside composition of any one of embodiments 1 to 55, wherein the composition comprises at least 300ppm of the steviol glycoside component.

Embodiment 57 relates to the steviol glycoside composition of any one of embodiments 1 to 56, wherein the composition comprises from 100ppm to 1600ppm of rebaudioside M.

Embodiment 58 relates to the steviol glycoside composition of any one of embodiments 1 to 57, wherein the composition comprises at least 200ppm of rebaudioside M.

Embodiment 59 relates to the steviol glycoside composition of any one of embodiments 1 to 58, wherein the composition comprises from 200ppm to 1000ppm of rebaudioside M.

Embodiment 60 relates to a steviol glycoside composition according to any one of embodiments 1 to 59, wherein the composition comprises at least 300ppm of rebaudioside M.

Embodiment 61 relates to a steviol glycoside composition according to any one of embodiments 1 to 60, wherein the composition comprises from 400ppm to 800ppm of rebaudioside M.

Embodiment 62 is directed to the steviol glycoside composition of any one of embodiments 1 to 61, wherein the composition comprises at least 500ppm of rebaudioside M.

Embodiment 63 relates to a steviol glycoside composition according to any one of embodiments 1 to 62, wherein composition comprises from 100ppm to 1600ppm of an organoleptic modifier.

Embodiment 64 relates to a steviol glycoside composition according to any one of embodiments 1 to 63, wherein the composition comprises at least 200ppm of an organoleptic modifier.

Embodiment 65 relates to the steviol glycoside composition of any one of embodiments 1 to 64, wherein the composition comprises from 200ppm to 1000ppm of the organoleptic modifier.

Embodiment 66 relates to the steviol glycoside composition of any one of embodiments 1 to 65, wherein the composition comprises at least 300ppm of the sensory modifier.

Embodiment 67 relates to the steviol glycoside composition of any one of embodiments 1 to 66, wherein the composition comprises from 400ppm to 800ppm of the sensory modifier.

Embodiment 68 relates to the steviol glycoside composition of any one of embodiments 1 to 67, wherein the composition comprises at least 500ppm of the sensory modifier.

Embodiment 69 relates to the steviol glycoside composition of any one of embodiments 1 to 68, wherein the composition comprises from 50ppm to 1400ppm of the salt of caffeoylquinic acid.

Embodiment 70 relates to the steviol glycoside composition of any one of embodiments 1 to 69, wherein the composition comprises at least 100ppm of a salt of caffeoylquinic acid.

Embodiment 71 relates to the steviol glycoside composition of any one of embodiments 1 to 70, wherein the composition comprises from 100ppm to 900ppm of the salt of caffeoylquinic acid.

Embodiment 72 relates to the steviol glycoside composition of any one of embodiments 1 to 71, wherein the composition comprises at least 150ppm of the salt of caffeoylquinic acid.

Embodiment 73 relates to the steviol glycoside composition of any one of embodiments 1 to 72, wherein the composition comprises from 200ppm to 720ppm of the salt of caffeoylquinic acid.

Embodiment 74 relates to the steviol glycoside composition of any one of embodiments 1 to 73, wherein the composition comprises at least 250ppm of a salt of caffeoylquinic acid.

Embodiment 75 relates to the steviol glycoside composition of any one of embodiments 1 to 74, wherein the weight ratio of steviol glycoside component to sensory modifier in the composition is from 1: 0.3 to 1: 3.

Embodiment 76 relates to the steviol glycoside composition of any one of embodiments 1 to 75, wherein the weight ratio of steviol glycoside component to sensory modifier in the composition is from 1: 0.3 to 1: 1.

Embodiment 77 relates to the steviol glycoside composition of any one of embodiments 1 to 76, wherein the weight ratio of steviol glycoside component to organoleptic modifier in the composition is about 2: 1.

Embodiment 78 relates to the steviol glycoside composition of any one of embodiments 1 to 77, wherein the amount effective to reduce sweet aftertaste lingering is determined by at least four panelists trained in tasting the steviol glycoside composition using the round table method using a scale of 0 to 6, wherein a score of 0 indicates no sweet aftertaste lingering and a score of 6 indicates extreme sweet aftertaste lingering, and wherein the sweet aftertaste lingering score is reduced by at least 1 unit as compared to a control sample lacking the sensory modifier.

Embodiment 79 relates to the steviol glycoside composition of any one of embodiments 1 to 78, wherein the effective amount reduces the sweet lingering score by at least 2 units compared to a control sample lacking the sensory modifier.

Embodiment 80 relates to the steviol glycoside composition of any one of embodiments 1 to 79, wherein the effective amount reduces the sweet lingering score by at least 3 units as compared to a control sample lacking the sensory modifier.

Embodiment 81 relates to the steviol glycoside composition of any one of embodiments 1 to 80, wherein the effective amount reduces the sweet lingering score to less than 3 units compared to a control sample lacking the sensory modifier.

Embodiment 82 relates to the steviol glycoside composition of any one of embodiments 1 to 81, wherein the steviol glycoside composition has a reduced lingering sweet aftertaste as compared to steviol glycosides without organoleptic modifiers.

Embodiment 83 is directed to the steviol glycoside composition of any one of embodiments 1 to 82, wherein the amount effective to reduce bitter taste is determined by at least four panelists trained to taste steviol glycoside compositions using a round table method using a scale of 0 to 6, wherein a score of 0 indicates no bitter taste and a score of 6 indicates extreme bitter taste, and wherein the bitter taste score is reduced by at least 1 unit as compared to a control sample lacking the sensory modifier.

Embodiment 84 relates to the steviol glycoside composition of any one of embodiments 1 to 83, wherein the effective amount reduces bitterness score by at least 2 units as compared to a control sample lacking the sensory modifier.

Embodiment 85 relates to the steviol glycoside composition of any one of embodiments 1 to 83, wherein the effective amount reduces bitterness score by at least 3 units compared to a control sample lacking the sensory modifier.

Embodiment 86 relates to the steviol glycoside composition of any one of embodiments 1 to 83, wherein the effective amount reduces the bitterness score to less than 2 units compared to a control sample lacking the sensory modifier.

Embodiment 87 relates to the steviol glycoside composition of any one of embodiments 1 to 83, wherein the effective amount reduces the bitterness score to less than 1 unit compared to a control sample lacking the sensory modifier.

Embodiment 88 relates to the steviol glycoside composition of any one of embodiments 1 to 87, wherein the steviol glycoside composition has a reduced bitterness as compared to a control sample lacking the sensory modifier.

Embodiment 89 relates to the steviol glycoside composition of any one of embodiments 1 to 88, wherein the composition is an aqueous solution.

Embodiment 90 relates to the steviol glycoside composition of any one of embodiments 1 to 89, wherein the composition is in solid form.

Embodiment 91 relates to the steviol glycoside composition of any one of embodiments 1 to 90, wherein the composition is a freeze-dried powder.

Embodiment 92 relates to the steviol glycoside composition of any one of embodiments 1 to 91, wherein the concentration of steviol glycoside component is from 200ppm to 1000ppm and the concentration of sensory modifier is from 200ppm to 1000 ppm.

Embodiment 93 relates to the steviol glycoside composition of any one of embodiments 1 to 92, wherein the concentration of steviol glycoside component is from 400ppm to 800ppm and the concentration of sensory modifier is from 400ppm to 800 ppm.

Embodiment 94 relates to the steviol glycoside composition of any one of embodiments 1 to 93, wherein the composition has a reduced lingering sweet aftertaste compared to the same composition lacking the sensory modifier.

Embodiment 95 relates to the steviol glycoside composition of any one of embodiments 1 to 94, wherein the composition has a reduced bitterness as compared to the same composition lacking the sensory modifier.

Embodiment 96 relates to the steviol glycoside composition of any one of embodiments 1 to 95, wherein the sensory modifier is in an amount effective to reduce the lingering sweet aftertaste.

Embodiment 97 relates to the steviol glycoside composition of any one of embodiments 1 to 96, wherein the sensory modifier is in an amount effective to reduce bitter taste.

Embodiment 98 relates to the steviol glycoside composition of any one of embodiments 1 to 97, wherein the lingering sweet aftertaste, the bitter taste, or both, is associated with rebaudioside M, rebaudioside N, rebaudioside O, rebaudioside D or a combination thereof.

Embodiment 99 relates to a beverage comprising the steviol glycoside composition of any one of embodiments 1 to 98.

Embodiment 100 relates to a pharmaceutical composition, dental composition, chewing gum or solid foodstuff comprising the steviol glycoside composition according to any one of embodiments 1 to 98.

Embodiment 101 relates to a method for reducing undesirable sensory attributes of an aqueous steviol glycoside solution, the method comprising dissolving a composition according to any one of embodiments 1 to 98 in an aqueous steviol glycoside solution.

Embodiment 102 relates to the method of embodiment 99, wherein the undesirable sensory attribute is bitterness, lingering sweetness linger, sharp taste, poor mouthfeel, astringency, or a rebaudioside M attribute.

Embodiment 103 relates to the method of embodiment 101, wherein the undesirable sensory attribute is bitter taste.

Embodiment 104 relates to the method of embodiment 101, wherein the undesirable sensory attribute is sweet lingering.

The embodiment 105 relates to the method of embodiment 101, wherein the undesirable sensory attribute is a rebaudioside M attribute selected from one or more of a metallic attribute, a powder attribute, a numb attribute, and a vapor attribute.

Embodiment 106 relates to a method for reducing the lingering sweet aftertaste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce the lingering sweet aftertaste of the steviol glycoside component,

wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the salt form.

Embodiment 107 relates to a method for reducing the lingering sweet aftertaste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce the lingering sweet aftertaste of the steviol glycoside component,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid, and

wherein the salt fraction comprises at least 50 wt% of the total sensory modifier.

Embodiment 108 relates to a method for reducing bitter taste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce the bitter taste of the steviol glycoside component,

wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the salt form.

Embodiment 109 relates to a method for reducing bitter taste from a steviol glycoside component in an edible composition, the method comprising combining the steviol glycoside component and an amount of an organoleptic modifier effective to reduce the bitter taste of the steviol glycoside component,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid, and

wherein the salt fraction comprises at least 50 wt% of the total sensory modifier.

Embodiment 110 relates to the method of any one of embodiments 99 to 107, wherein the steviol glycoside component and the organoleptic modifier are added simultaneously.

Embodiment 111 relates to an aqueous steviol glycoside solution with reduced lingering sweet aftertaste comprising:

a steviol glycoside component comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside a, wherein the total steviol glycoside component concentration is from 200ppm to 1000 ppm; and

a sensory modifier at a concentration of 200ppm to 1000ppm,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid,

wherein the salt fraction comprises from 50 wt% to 80 wt% of the total sensory modifier, wherein at least a portion of the sensory modifier is prepared from mate tea or stevia, and

wherein the aqueous steviol glycoside solution has a reduced lingering sweet aftertaste as compared to an aqueous steviol glycoside solution having the same concentration of the same steviol glycoside component without the sensory modifier.

Embodiment 112 relates to an aqueous steviol glycoside solution with reduced bitter taste comprising:

a steviol glycoside component comprising at least one of rebaudioside D, rebaudioside M, and rebaudioside a, wherein the total steviol glycoside concentration is from 400ppm to 800 ppm; and

a sensory modifier at a concentration of 400ppm to 800ppm,

wherein the sensory modifier comprises a salt fraction and an acid fraction,

wherein the salt fraction comprises one or more compounds selected from the group consisting of salts of monocaffeoylquinic acid and salts of dicaffeoylquinic acid,

wherein the acid fraction comprises one or more compounds selected from the group consisting of monocaffeoylquinic acid and dicaffeoylquinic acid,

wherein the salt fraction comprises from 50 to 80 wt% of the total sensory modifier and the acid fraction comprises from 20 to 50 wt% of the total sensory modifier,

wherein at least a portion of the sensory modifier is prepared from mate tea or stevia rebaudiana, and

wherein the aqueous steviol glycoside solution has a reduced bitterness as compared to an aqueous steviol glycoside solution having the same concentration of the same steviol glycoside component without the organoleptic modifier.

Embodiment 113 relates to a steviol glycoside composition comprising:

from about 200ppm to about 800ppm of a steviol glycoside component comprising rebaudioside D and rebaudioside M, wherein rebaudioside M comprises at least 80% by weight of the steviol glycoside component; and

from about 200ppm to about 400ppm of a sensory modifier, wherein the sensory modifier is a mixture comprising one or more caffeoyl-substituted quinic acids and one or more salts thereof, and at least 50% by weight of the sensory modifier is in the salt form.

Embodiment 114 is directed to a steviol glycoside composition of claim 113, wherein composition has a rounded mouthfeel profile, only a weak sweet aftertaste lingering, a sucrose-like mouthfeel, only a slight astringent taste, and only a trace amount of bitter taste.

Embodiment 115 relates to the steviol glycoside composition of claim 113, wherein the composition has a rounded mouthfeel profile, only a weak sweet aftertaste lingering, a sucrose-like mouthfeel, only a slight astringent taste and only a trace amount of bitter taste.