Cooling composition
阅读说明：本技术 清凉组合物 (Cooling composition ) 是由 A·胡布克斯 W·菲波 P·比乌索布莱 于 2018-07-12 设计创作，主要内容包括：本发明涉及调味料或香料领域。更具体而言,涉及一种物质组合物,包含：i)至少一种式(I)的化合物,<Image he="376" wi="700" file="DDA0002364045060000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>该化合物为其任何立体异构体的形式；其中R<Sup>1</Sup>代表可选地被一个或两个C<Sub>1-3</Sub>烷基或烷氧基或被一个或两个卤基取代的苯基；R<Sup>2</Sup>和R<Sup>3</Sup>彼此独立地代表杂环基,其包含1-3个选自氮、氧和硫的杂原子,其可选地被一个或两个C<Sub>1-3</Sub>烷基取代；和ii)至少一种C<Sub>1-6</Sub>直链或支化的乳酸烷基酯。所述物质组合物在调味料或香料组合物中的用途也是本发明的一部分。因此,按照本文所述,本发明包括作为调味或加香组合物的一部分或调味或加香消费品的一部分的本发明的物质组合物。制备本发明的物质组合物和式(I)化合物特别是N-(1H-吡唑-3-基)-N-(噻吩-2-基甲基)-2-(对甲苯氧基)乙酰胺的多晶型物的方法也是本发明的目的。(The present invention relates to the field of flavours or fragrances. More specifically, it relates to a composition of matter comprising: i) at least one compound of formula (I), the compound is any ofThe stereoisomeric forms; wherein R is 1 Represents optionally one or two C 1‑3 Alkyl or alkoxy or phenyl substituted with one or two halo; r 2 And R 3 Independently of one another, represents a heterocyclic radical comprising 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, which may optionally be interrupted by one or two C 1‑3 Alkyl substitution; and ii) at least one C 1‑6 Linear or branched alkyl lactate. The use of the composition of matter in a flavour or fragrance composition is also part of the invention. Thus, as described herein, the present invention includes the composition of matter of the present invention as part of a flavoring or perfuming composition or as part of a flavoring or perfuming consumer product. The process for preparing the composition of matter of the invention and the polymorphic forms of the compound of formula (I), in particular N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) -2- (p-tolyloxy) acetamide, are also an object of the invention.)
1. A composition of matter comprising:
i) at least one compound of formula (I),
the compound is in the form of any of its stereoisomers; wherein R is1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo; r2And R3Independently of one another, represents a heterocyclic radical containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3Alkyl substitution; and
ii) at least one C1-6Linear or branched alkyl lactate.
2. Composition according to claim 1, characterized in that R1Representing one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo groups.
3. Composition according to any one of claims 1 to 2, characterized in that R1RepresentsBy one or two C1-2Alkyl or alkoxy or phenyl substituted with one or two fluoro groups.
4. Composition according to any one of claims 1 to 3, characterized in that R1Represents phenyl substituted by one or two methyl, ethyl, methoxy or one fluoro groups.
5. Composition according to any one of claims 1 to 4, characterized in that R2And R3Independently of one another, represents a heterocyclic radical comprising 1 to 3 heteroatoms selected from nitrogen and sulfur.
6. Composition according to any one of claims 1 to 5, characterized in that R2Represents a heterocyclic group containing one or two nitrogen atoms.
7. Composition according to any one of claims 1 to 6, characterized in that R2Represents pyrazolyl.
8. Composition according to any one of claims 1 to 7, characterized in that R3Represents a heterocyclic group containing one or two sulfur atoms.
9. Composition according to any one of claims 1 to 8, characterized in that R3Represents a thienyl group.
10. Composition according to any one of claims 1 to 9, characterized in that C is1-6The linear or branched alkyl lactate is ethyl lactate.
11. Composition according to any one of claims 1 to 10, characterized in that it comprises from 0.1% to 20% by weight, relative to the total weight of the composition, of at least one compound of formula (I) as defined in claims 1 to 9, and from 80% to 99.1% by weight, relative to the total weight of the composition, of at least one C1-6Straight-chain or branched lactic acid alkylAnd (3) an ester.
12. Composition according to any one of claims 1 to 11, characterized in that the compound of formula (I) is N- (1H-pyrazol-5-yl) -N- (thien-2-ylmethyl) -2- (p-tolyloxy acetamide, N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) -2- (p-tolyloxy) acetamide, 2- (4-ethylphenoxy) -N- (1H-pyrazol-5-yl) -N- (thiophen-2-ylmethyl) acetamide or 2- (4-ethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide.
13. A flavoring composition comprising:
i) at least one compound comprising at least one compound of formula (I) and at least one C as defined in claims 1 to 121-6A composition of matter of linear or branched alkyl lactate;
ii) at least one ingredient selected from the group consisting of flavor carriers, flavor co-ingredients, and mixtures thereof; and
iii) optionally, at least one flavor adjuvant.
14. Flavouring composition according to claim 13, characterized in that it comprises at least one cooling agent.
15. Seasoning composition according to claim 14, characterized in that the cooling agent is selected from the group consisting of: menthol, menthol methyl ether, menthone glycerol acetal (FEMA GRAS'3807), menthone glycerol ketal (FEMA GRAS 3808), menthyl lactate (FEMA GRAS 3748), menthol ethylene carbonate (FEMA GRAS 3805), menthol propylene carbonate (FEMA GRAS 3806), menthyl-N-ethyl oxalate, monomenthyl succinate (FEMA GRAS3810), glutamic acid monomenthyl ester (FEMA GRAS 4006), menthoxy-1, 2-propanediol (FEMA GRAS 3784), menthoxy-2-methyl-1, 2-propanediol (FEMA GRAS 3849), (1R,2S,5R) -N- (4- (cyanomethyl) phenyl) menthyl carboxamide (FEMA GRAS4496), (1R,2S,5R) -N- (2- (pyridin-2-yl) ethyl) menthyl carboxamide (FEMA GRAS4549), menthane carboxylic acid esters and amides WS-3, WS-4, WS-5, WS-12, WS-14, WS-23 (2-isopropyl-N, 2, 3-trimethylbutanamide, FEMA GRAS 3804) WS-30 and mixtures thereof.
16. A flavoured consumer product comprising a composition of matter as defined in any of claims 1 to 12 or a flavouring composition as defined in claims 13 to 15.
17. A flavoured consumer product according to claim 16, characterized in that the flavoured consumer product is a seasoning, a condiment, a meat product, a soup, a carbohydrate product, a dairy or fat product, a salty product, a confectionery, an oral care product, an artificial food, a pet or animal food, or a beverage.
18. A flavoured consumer product according to claim 17, characterized in that the flavoured consumer product is a soup base, a stock bar, a powder mixture, a sauce, a dressing, a barbecue sauce, a dressing, a gravy, a sweet sauce, a sour sauce, a salad dressing or a mayonnaise, a poultry, beef or pork meat product, seafood, surimi, or fish sausage, broth, a cream soup, a chicken or beef soup, or a tomato or asparagus soup, instant noodles, rice, pasta, potato chips or chips, pizza, tortillas, noodles, spreads, cheese, regular or low fat margarine, a butter/margarine mixture, butter, peanut butter, shortening, processed or flavoured cheese, snacks, snack foods, potato chips, egg products, potato/corn chips, microwave oven popcorn, nuts, pretzels, rice cake, artificial dairy product, artificial seafood, artificial meat, pet or animal food, ready-to-drink beverage, powdered soft drink, hot drink, tea, soft drink, carbonated soft drink, alcoholic beverage, ready-to-drink or powdered soft drink, baked confectionery, tara peel, cake, confectionery, candy, sweet nut, chocolate, chewing gum, bubble gum, confection, candy piece, sugar-free candy, chocolate candy, toothpaste, mouthwash, dental care product, denture adhesive, dental water, oral spray or dental floss.
19. A perfuming composition comprising:
i) at least one compound comprising at least one compound of formula (I) and at least one C as defined in claims 1 to 121-6A composition of matter of linear or branched alkyl lactate;
ii) at least one ingredient selected from the group consisting of a fragrance carrier, a perfuming co-ingredient, and mixtures thereof; and
iii) optionally, at least one flavor adjuvant.
20. A perfumed consumer product comprising the composition of matter as defined in any one of claims 1 to 12 or the perfuming composition as defined in claim 19.
21. A perfumed consumer product according to claim 20, characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin care product, an air care product or a home care product.
22. A perfumed consumer product according to claim 21, characterized in that the perfumed consumer product is a fine perfume, an eau de toilette or eau de toilette, a cologne, a shaving or after-shave lotion, a liquid or solid detergent, a fabric softener, a liquid or solid odour enhancer, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain care product, a shampoo, a colourant, a hair spray, a colour care product, a hair styling product, a dental care product, a disinfectant, a personal care product, a skin cream or lotion, a vanishing cream, a body balm or antiperspirant, a depilatory, a tanning or sun-care product, a nail product, a skin cleaner, a cosmetic, a perfumed soap, a bath mousse, a bath or oil or gel, a foot/hand care product, a hygiene product, an air freshener, a "ready to use" powdered air freshener, a mould remover, Furniture care products, wipes, dishwashing or hard-surface detergents, leather care products, automotive care products.
23. A method of imparting, enhancing, improving or modifying the taste properties of a flavouring composition or a flavoured article or surface, which method comprises adding to said composition or article an effective amount of a composition of matter according to the invention as defined in any of claims 1 to 12.
24. A method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or surface, which method comprises adding to said composition or article an effective amount of a composition of matter as defined in any one of claims 1 to 12.
25. A process for preparing a composition of matter as defined in claims 1 to 12, comprising the steps of:
a) preparing a compound of formula (I) as defined in claim 1 by reacting a compound of formula (II) with a compound of formula (III),
wherein R is1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo; x represents hydroxy, C1-10An alkoxy group or a chlorine atom;
wherein R is2And R3Independently of one another, represents a heterocyclic radical containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3Alkyl substitution;
b) crystallizing the reaction mixture obtained in step a);
c) filtering the solution of the crystalline product obtained in step b);
d) drying the crystalline product obtained in step c); and
e)dissolving the dried crystalline product obtained in step d) in C1-6Linear or branched alkyl lactate.
26. The method of claim 25, wherein X represents C1-5Alkoxy, preferably C1-3An alkoxy group.
27. Process according to any one of claims 25 to 26, characterized in that step a) is carried out in the presence of a base.
28. A process according to claim 27, characterised in that the base is an alkali metal alkoxide, carbonate or hydroxide.
29. Process according to any one of claims 25 to 28, characterized in that steps c) to e) of the process according to the invention are carried out in the same apparatus.
30. A crystalline form of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide characterized by its main peaks at 6.86,12.46,15.87,17.38,17.70,17.93,18.43,19.46,20.61,22.08,23.03,23.43,24.36,26.11,27.59,34.68 obtained by irradiation with copper K- α in a powder X-ray diffraction pattern.
Technical Field
The invention relates to the field of seasonings (edible essence) or spices (daily chemical essence). More particularly, the invention relates to a composition comprising at least one compound of formula (I) and at least one C1-6Linear or branched alkyl lactate, and the use of said composition of matter in a flavour or fragrance composition. Thus, as described herein, the present invention includes the composition of matter of the present invention as part of a flavoring or perfuming composition or as part of a flavoring or perfuming consumer product. The process for preparing the composition of matter of the invention and the polymorphic forms of the compound of formula (I), in particular N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) -2- (p-tolyloxy) acetamide, are also an object of the invention.
Background
One of the most desirable ingredients in the field of perfumery and flavoring is an ingredient that imparts a freshness and clean feel to consumer products, which is used in a variety of perfumed and flavored consumer products. For decades, many efforts have been made to obtain compounds having this effect.
In this respect, very intense novel cooling substances have been reported in WO2012/061698 and WO2017/058594, which are modulators of the transient receptor potential channel type M member 8(TRPM8), which is a channel specifically involved in cooling sensation. These compounds are particularly effective and provide a cooling effect at very low concentrations. In fact, a cooling effect can be observed with only a trace amount of this powder. However, the compounds are in the form of very fine powders at room temperature and atmospheric pressure. Due to the strength of these compounds, they should be diluted in solvents, in particular solvents approved in flavoured consumer products. However, the compounds have low solubility in the most common flavor solvents.
Thus, it is desirable to solubilize these compounds to provide them in a diluted form. The present invention provides a solution to the above problems by using alkyl lactate.
Disclosure of Invention
The present invention relates to a novel composition comprising at least one compound of formula (I) and at least one C1-6Linear or branched alkyl lactate which may facilitate the use and handling of the compound of formula (I).
Accordingly, a first object of the present invention is a composition of matter comprising:
i) at least one compound of formula (I),
the compound is in the form of any of its stereoisomers; wherein R is1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo; r2And R3Independently of one another, represents a heterocyclic radical containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3Alkyl substitution; and
ii) at least one C1-6Linear or branched alkyl lactate.
A second object of the invention is a flavouring composition comprising:
i) at least one composition of matter comprising at least one compound of formula (I) and at least one C1-6Linear or branched alkyl lactate;
ii) at least one ingredient selected from the group consisting of flavor carriers, flavor co-ingredients, and mixtures thereof; and
iii) optionally, at least one flavor adjuvant.
A third object of the present invention is a flavoured consumer product comprising a composition of matter as defined above or a flavouring composition as defined above.
Another object of the present invention is a perfuming composition comprising:
i) at least one composition of matter comprising at least one compound of formula (I) and at least one C1-6Linear or branched alkyl lactate;
ii) at least one ingredient selected from the group consisting of a fragrance carrier, a perfuming co-ingredient, and mixtures thereof; and
iii) optionally, at least one flavor adjuvant.
Another object of the present invention is a perfumed consumer product comprising a composition of matter as defined above or a perfuming composition as defined above.
Another object of the present invention is a method of imparting, enhancing, improving or modifying the taste properties of a flavouring composition or a flavoured article or surface, which method comprises adding to said composition or article an effective amount of a composition of matter according to the present invention, for example to impart typical notes thereto.
Another object of the present invention is a method to confer, enhance, improve or modify the odor properties of a perfuming composition or of a perfumed article or surface, which method comprises adding to said composition or article an effective amount of a composition of matter as defined above.
Another object of the present invention is a process for preparing a composition of matter as defined above, comprising the following steps:
a) preparing a compound of formula (I) as defined in claim 1 by reacting a compound of formula (II) with a compound of formula (III),
wherein R is1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo; x represents hydroxy, C1-10An alkoxy group or a chlorine atom;
wherein R is2And R3Independently of one another, represents a heterocyclic radical containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3Alkyl substitution;
b) crystallizing the reaction mixture obtained in step a);
c) filtering the solution of the crystalline product obtained in step b);
d) drying the crystalline product obtained in step c); and
e) dissolving the dried crystalline product obtained in step d) in C1-6Linear or branched alkyl lactate.
A final object of the invention is a crystalline form of N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, characterized by its main peaks located at 6.86,12.46,15.87,17.38,17.70,17.93,18.43,19.46,20.61,22.08,23.03,23.43,24.36,26.11,27.59,34.68, obtained by irradiation with copper K- α in its powder X-ray diffraction diagram.
Drawings
FIG. 1 shows the 13C solid state NMR spectrum obtained as described in example 3.
Figure 2 shows the X-ray powder diffraction spectrum obtained as described in example 3.
Detailed Description
Surprisingly, it has now been found that the compounds of formula (I) can be readily dissolved in C1-6In linear or branched alkyl lactate, this allows the use of the compounds at very low levels, while reducing the handling of these compounds in solid form.
Accordingly, a first object of the present invention is a composition of matter comprising:
i) at least one compound of formula (I),
the compound is in the form of any one of its stereoisomers; wherein R is1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo; r2And R3Independently of one another, represents a heterocyclic radical containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionally substituted by one or two C1-3Alkyl substitution; and
ii) at least one C1-6Linear or branched alkyl lactate.
For the sake of clarity, the expression "any one of its stereoisomers" or similar terms is used to indicate the normal meaning understood by a person skilled in the art, i.e. the compound of formula (I) is in the form of any diastereoisomer, enantiomer or mixture thereof. In other words, the compounds of formula (I) have amide functionality which may be cis or trans, or mixtures thereof. Furthermore, the compounds of formula (I) may additionally have at least one stereogenic center, which may have different stereochemistry (i.e., when one stereogenic center is present, compound (I) may have either the (R) or (S) configuration). Each of said stereogenic centers may be in the relative configuration R or S or a mixture thereof. The compounds of formula (I) may be in the form of pure enantiomers or diastereomers, or in the form of mixtures of stereoisomers.
According to any of the above embodiments, R1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo groups. Preferably, R1Representing one or two C1-3Alkyl or alkoxy groups or phenyl groups substituted with one or two halogen atoms. Preferably, R1Representing one or two C1-2Alkyl or alkoxy or phenyl substituted with one or two fluoro. Even more preferably, R1Represents phenyl substituted by one or two methyl, ethyl, methoxy or by one fluoro group. Relative to oxygen atom and R1The bonds between the groups, the substituents of the phenyl groups may be in the ortho and/or meta and/or para positions. Preferably, R1May be selected from p-tolyl, 4-ethylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 3, 4-dimethylphenyl and m-tolyl. Even more preferably, R1It may be p-tolyl or 4-ethylphenyl. Even more preferably, R1May be p-tolyl.
The terms "ortho", "meta" and "para" refer to the normal meanings in the art. I.e. the ortho-positions correspond to the two substituents on the phenyl group occupying positions adjacent to each other; the meta position corresponds to two substituents on the phenyl group occupying the 1 and 3 positions, while the para position corresponds to two substituents on the phenyl group occupying the 1 and 4 positions.
According to any of the above embodiments, R2And R3Independently of one another, represents a heterocyclic radical containing 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, which may optionally be interrupted by one or two C1-3Alkyl substitution. Preferably, R2And R3Independently of one another, represents a heterocyclic radical comprising 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur. Even more preferably, R2And R3Independently of one another, represents a heterocyclic radical comprising 1 to 3 heteroatoms selected from nitrogen and sulfur.
According to any of the above embodiments, R2Represents a heterocyclic group containing one or two nitrogen atoms. Preferably, R2Represents pyrazolyl.
According to any of the above embodiments, R3Represents a heterocyclic group containing one or two sulfur atoms. Preferably, R3Represents a thienyl group.
According to any of the above embodiments, the compound of formula (I) may be selected from N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, 2- (4-fluorophenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide, 2- (4-ethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide, 2- (4-methoxyphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide, n- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (m-tolyloxy) acetamide and 2- (3, 4-dimethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) acetamide. The compound has a pyrazolyl group. It is well known that this group exists in two tautomeric forms. Namely 1H-pyrazol-3-yl and 1H-pyrazol-5-yl. The two forms equilibrate very rapidly. In other words, when the composition of matter of the invention comprises N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, the composition inevitably also comprises N- (1H-pyrazol-5-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide. The same is true for the other compounds listed above. I.e. 2- (4-fluorophenoxy) -N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) acetamide is in equilibrium with 2- (4-fluorophenoxy) -N- (1H-pyrazol-5-yl) -N- (thien-2-ylmethyl) acetamide, 2- (4-ethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) acetamide is in equilibrium with 2- (4-ethylphenoxy) -N- (1H-pyrazol-5-yl) -N- (thien-2-ylmethyl) acetamide, 2- (4-methoxyphenoxy) -N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) acetamide is in equilibrium with 2- (4-methoxyphenoxy) -N- (1H-pyrazol-5-yl) -N- (thien-2-ylmethyl) acetamide, N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) -2- (m-tolyloxy) acetamide is in equilibrium with N- (1H-pyrazol-5-yl) -N- (thien-2-ylmethyl) -2- (m-tolyloxy) acetamide, while 2- (3, 4-dimethylphenoxy) -N- (1H-pyrazol-3-yl) -N- (thien-2-ylmethyl) acetamide is in equilibrium with 2- (3, 4-dimethylphenoxy) -N- (1H-pyrazol-5-yl) -N- (thien-2-ylmethyl) acetamide. Preferably, the compound of formula (I) is N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide.
According to any of the above embodiments, the composition of matter comprises C1-6Linear or branched alkyl lactate. Preferably, the composition of matter comprises C1-4Linear or branched alkyl lactate. Even more preferably, the composition of matter comprises C1-4A linear alkyl lactate. Even more preferably, the composition of matter comprises ethyl lactate.
According to any one of the above embodiments, the composition of matter comprises from 0.1% to 20% by weight, relative to the total weight of the composition, of at least one compound of formula (I), and from 80% to 99.9% by weight, relative to the total weight of the composition, of at least one C1-6Linear or branched alkyl lactate. Preferably, the composition of matter comprises from 0.5% to 15% by weight, relative to the total weight of the composition, of at least one compound of formula (I), and from 85% to 99.5% by weight, relative to the total weight of the composition, of at least one C1-6Linear or branched alkyl lactate. Even more preferably, the composition of matter comprises from 1% to 10% by weight, relative to the total weight of the composition, of at least one compound of formula (I), and from 90% to 99% by weight, relative to the total weight of the composition, of at least one C1-6Linear or branched alkyl lactate.
The composition of matter of the invention can be used as a flavouring ingredient. The invention relates to a pharmaceutical composition comprising at least one compound of formula (I) and at least one C1-6Use of a composition of matter of linear or branched alkyl lactate as a flavouring ingredient. In other words, it relates to a method or process of imparting, enhancing, improving or modifying the taste properties of a flavouring composition or a flavoured article or surface, which method comprises adding to said composition or article an effective amount of a composition of matter according to the invention, for example to impart typical notes thereto.
By "use of a composition of matter", it must also be understood herein that the composition comprises at least one compound of formula (I) and at least one C1-6Use of linear or branched alkyl lactate, and any composition that can be advantageously used in the flavor industry.
By "taste" is meant specifying taste perception and taste sensation.
Said composition, which can in fact be advantageously used as a flavouring ingredient, is also an object of the present invention.
Therefore, another object of the present invention is a flavouring composition comprising:
i) at least one compound as defined above comprising at least one compound of formula (I) and at least one C1-6A composition of matter of linear or branched alkyl lactate;
ii) at least one ingredient selected from the group consisting of flavor carriers, flavor co-ingredients, and mixtures thereof; and
iii) optionally, at least one flavor adjuvant.
By "flavor carrier" is meant a material that is substantially neutral from a flavor standpoint, so long as it does not significantly alter the organoleptic properties of the flavor ingredient. The carrier may be a liquid or a solid.
Suitable liquid carriers include, for example, emulsifying systems, i.e., solvent and surfactant systems, or solvents commonly used in flavorings. A detailed description of the nature and type of solvents commonly used in flavors is not exhaustive. Suitable solvents include, for example, propylene glycol, triacetin, neobee, triethyl citrate, benzyl alcohol, ethanol, vegetable oils such as linseed oil, sunflower oil or coconut oil or terpenes.
Suitable solid carriers include, for example, absorbent gums or polymers, or even encapsulating materials. Examples of such materials may include wall-forming materials and plasticizing materials, such as mono-, di-or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinyl alcohols, proteins or pectins, or as described in references such as H.Scherz, Hydrokolloides: Stabilisatoren, Dicklungs-und Geliermentil in Lebensmittel, Band2der Schriferenreihe Lebensmittellchemie,
By "flavor co-ingredient" is meant herein a compound that is used in a flavor formulation or composition to impart a hedonic effect. In other words, such a co-ingredient to be considered as a flavouring co-ingredient must be recognized by a person skilled in the art as being able to impart or modify in an active or pleasant way the taste of the composition, and not just as having a taste. The flavouring ingredient is not a compound of formula (I).
The nature and type of the flavouring co-ingredients present in the flavouring composition are not described in more detail here and the skilled person will be able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these flavor co-ingredients fall into the following chemical classes: alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. In any event, many of these co-ingredients are listed in references such as the works per and flavour chemicals of s.arctander, 1969, montcalair, New Jersey, USA or other works of a newer version or similar nature, and in a large number of patent documents in the field of flavorings. It will also be appreciated that the co-ingredients may also be compounds known to release various types of flavouring compounds in a controlled manner.
In particular, flavoring co-ingredients commonly used in flavoring formulations can be cited: essential oils obtained from mint plants, such as peppermint (peppermint), spearmint and peppermint from Japanese, peppermint (mint pepper) oil and other extracts (Absolute), oleoresin, washed (washed) oil, refined peppermint (mintperita Rectified India) oil and other extracts (Absolute, oleoresin, washed oil), peppermint native (spica native) oil and other extracts (Absolute, oleoresin, washed oil), peppermint american (spica) oil and other extracts (Absolute, oleoresin, washed oil), peppermint (mint arvensis) oil and other extracts (Absolute, oleoresin, washed oil), spearmint (mint cardiaca) oil and other extracts (Absolute, oleoresin, washed oil), oil from all mint varieties obtainable from breeding, such as the hybrid mint plants known as S3513-12, oil from the mint species (known as peppermint-3513-12), oil from the mint species of mint species known as peppermint-oil and other extracts from breeding 13-39-9, 13-a36-13, 07-A3-11, 09-6-2, 11-a35-3, 07-A3-5A, 14-27-71, 08-6-10, 14-41-16, 08-a20-3, 14-27-89, 05-19-1) oils, eucalyptus globulus (eucalyptus globulus) oil and other extracts (neat oil, oleoresin, washed oil), eucalyptol, anethole (Anethol) (natural and synthetic), anise oil, basil oil, clove oils of all types (bud, stem, leaf), eugenol, cinnamaldehyde, cassia seed oil, cinnamon bark oil, cinnamon leaf oil, cinnamon bud oil, menthol (all grades: l and DL (racemic), pine oil (all types and sources), sage oil and other extracts (neat oil, oleoresin, washed oil), chamomile and other extracts (neat oil, oleoresin, washed oil), vanillin (natural and synthetic) and other extracts (neat oil, oleoresin, washed oil), lemon oil, orange oil and other extracts (neat oil, oleoresin, washed oil), lime oil and other extracts (neat oil, oleoresin, washed oil), citrus oil, tangerine oil, maltol, ethyl maltol, furanone, benzophenone, all lactones, ethyl butyrate, licorice extract, (Z) -3-hexenyl acetate, (Z) -3-hexen-1-ol, (E) -2-hexen-1-ol or methyl salicylate. It is well recognized by those skilled in the art that natural oils can be replaced by synthetic and artificial blends that mimic the sensory characteristics of natural oils. The blends may also be used as flavor co-ingredients.
By "flavor adjuvant" is meant herein an ingredient capable of imparting additional added benefits such as color, specific lightfastness, chemical stability, and the like. A detailed description of the nature and type of adjuvants commonly used in flavouring compositions is not exhaustive. However, such adjuvants are well known to the person skilled in the art and they will be able to select them on the basis of their general knowledge and according to the intended use or application.
In addition to a composition comprising at least one compound of formula (I), at least one C1-6A linear or branched alkyl lactate, at least one flavor carrier,At least one compound of formula (I), at least one C, in addition to the flavor composition of at least one flavor co-ingredient and optionally at least one flavor adjuvant1-6A composition of linear or branched alkyl lactate and at least one flavor carrier also represents a specific embodiment of the present invention.
Non-limiting examples of suitable cooling agents according to any of the above embodiments include methyl-7- (2-isopropyl-N, 2, 3-trimethylbutanamide), ethyl-3- (N-ethyl-p-menthane-3-carboxamide), methyl-3- (FEMA-3-ethyl) -3-carboxamide, ethyl-3- (FEMA-3-ethyl) -5- [3- (p-menthane-3-carboxamido) acetic acid ethyl ester, FEMA 4309, WS-12- (1R,2S,5R) -N- (4-methoxyphenyl) -p-menthane carboxamide, FEMA 4681, WS-27 (N-ethyl-2, 2-diisopropylbutanamide), FEMA 57, N-cyclopropyl-5-methyl-2-isopropylcyclohexanecarboxamide, FEMA 4693, WS-116(N- (1, 1-dimethyl-2-hydroxyethyl) -2, 2-diethylcarbamimidoyl) -2, 3-methyl-2-4- (3, 7, 3-propyl) -2-methyl-2-ethyl-3-menthyl) menthyl-2- (FEMA-propyl) -2,3- (FEMA-methyl-ethyl) -2-methyl-2-propyl-2-menthyl) 2- (FEMA-ethyl) -2-methyl-ethyl-3-menthyl) benzoic acid ester, 2- (FEMA-ethyl-2- (FEMA-propyl) -2- (FEMA-2-ethyl) -2-methyl-ethyl) -2-ethyl-2-methyl-ethyl-4- (FEN-methyl-ethyl) ethyl-2-methyl-7, FEMA-methyl-ethyl-methyl-2- (FEN-methyl-2-methyl-ethyl-2-methyl-ethyl-methyl-ethyl-2-ethyl-methyl-ethyl-2-methyl-3-ethyl-methyl-ethyl-4- (FEN-ethyl) ethyl-2-methyl-2-ethyl-methyl-ethyl-2-4- (FEN-ethyl-methyl-2-methyl-ethyl) ethyl-methyl-ethyl-methyl-ethyl-4- (FEN-ethyl) ethyl-4- (FEN-2-4-7, 2-ethyl) ethyl-2-methyl-2-methyl-ethyl-methyl-4-ethyl-methyl-4- (FER-4-methyl-2-7, 2-methyl-4-methyl-2-methyl-ethyl-methyl-ethyl-2-methyl-4-2-4-methyl-4-methyl-2-methyl-7-methyl-2-methyl-4-methyl-ethyl-4-methyl-4-methyl-ethyl-methyl-2-methyl-4-2-methyl-4-ethyl-2-4-ethyl-4-methyl-ethyl-methyl-4-ethyl-2-ethyl-2-methyl-ethyl-methyl-4-methyl-4-methyl-2-methyl-2-methyl-2-methyl-propyl-methyl-2-methyl-4-ethyl-4-propyl-ethyl-methyl-propyl-methyl-ethyl-4-methyl-propyl-methyl-ethyl-methyl-2-methyl-propyl-methyl-propyl-2-methyl-4-ethyl-methyl-2-methyl-propyl-methyl-propyl-methyl-4-methyl-4-ethyl-4-ethyl-methyl-2-4-ethyl-2-4-ethyl-4-methyl-ethyl-2-ethyl-methyl-2-propyl-4-methyl-ethyl-4-ethyl-methyl-ethyl-4-ethyl-4-methyl-ethyl-4-2-ethyl-methyl-4-propyl-4-methyl-4-methyl-2-propyl-methyl-propyl-2-propyl-methyl-2-methyl-4-methyl-4-propyl-methyl-4-methyl-propyl-methyl-4-methyl-2-methyl-ethyl-2-methyl-4-methyl-2-methyl-4-methyl-4-methyl-2-4-ethyl-methyl-4-methyl-ethyl-methyl-4-methyl-propyl-methyl-4-ethyl-methyl-ethyl-methyl-propyl-4-methyl-4-methyl-4-methyl-ethyl-4-methyl-4-methyl-4-methyl-4-methyl-4-propyl-4-methyl-4-methyl-4-methyl-4-propyl-4-propyl-methyl-4-ethyl-4-methyl.
According to any of the above embodiments, the composition of the invention may comprise a sweetener. Non-limiting examples of suitable sweeteners include common sugar sweeteners such as sucrose, fructose (e.g., D-fructose), glucose (e.g., D-glucose); sweetener compositions containing natural sugars, such as stevia (all types and grades), corn syrup (including high fructose corn syrup) or other syrups or sweetener concentrates from natural fruit and vegetable sources; semi-synthetic "sugar alcohol" sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol, xylitol, maltodextrin, glycerol, threitol, arabitol, ribitol, and galactitol; artificial sweeteners such as miraculin, aspartame, super-aspartame, saccharin sodium salt, acesulfame potassium, cyclamate sodium, and alitame; other sweeteners, such as trehalose, melezitose, melibiose, raffinose, palatinose, lactulose, cyclamic acid, mogroside, tagatose (e.g., D-tagatose), maltose, galactose (e.g., D-galactose), L-rhamnose, D-sorbose, mannose (e.g., D-mannose (D-maunose)), lactose, L-arabinose, D-ribose, D-glyceraldehyde, curculin, brazzein, mogroside, neohesperidin dihydrochalcone (NHDC), neotame and other aspartame derivatives, D-tryptophan, D-leucine, D-threonine, glycine, D-asparagine, D-phenylalanine, L-proline, maltitol, Hydrogenated Glucose Syrup (HGS), magap, sucralose, N- (4-cyanophenyl) -N- (2, 3-methylenedioxybenzyl) guanidinoacetic acid (Lugduname), sucronate, sucrootate, monatin, ganache, Hydrogenated Starch Hydrolysate (HSH), stevioside, rebaudioside a, rebaudioside D, rebaudioside M, and other sweet steviol glycosides, luo han guo, thaumatin, monellin, carrelame, and other guanidine-based sweeteners.
According to any of the above embodiments, the flavored composition may further comprise ingredients that impart warmth, tingling, salivation, cleansing, or an alcohol-enhancing effect, such as pepper extract, spice extract (e.g., ginger, cantaloupe (mangguette), various types of pepper, including Sichuan pepper (Sichuan), piperine, capsaicin, jambu (jambu) extract, and spilanthol (spilanthol).
According to any of the above embodiments, the flavouring composition of the invention may be in the form of a confectionery (confection), such as chewing gum, bubble gum, sugar tablets (pastillage), sugar-free candy or an oral care product, such as toothpaste, mouthwash, dental care product, denture adhesive, dental water, oral spray or dental floss.
Furthermore, the composition of matter of the invention can also be advantageously used in all fields of flavouring to actively impart or modify the taste of a consumer product to which said composition of matter is added. Thus, another object of the present invention is represented by a flavoured consumer product comprising the composition of the present invention as defined above.
The composition of matter of the invention may be added as such or as part of the flavouring composition of the invention.
For clarity, "flavoured consumer product" refers to an edible product, which may be a food or beverage, which may be fried or non-fried, and frozen and non-frozen, low-fat or fat-free, infused, mashed, refrigerated, dehydrated, ready-to-eat, canned, reconstituted, retorted or preserved. Thus, a flavoured article according to the present invention comprises the composition of the present invention, and optionally a benefit agent, which corresponds to the taste and flavour profile of a desired edible product, such as a soup cube.
The nature and type of the ingredients of the food or beverage do not warrant a more detailed description here, which the skilled person would be able to select on the basis of his general knowledge and according to the nature of the product in question.
Typical examples of said flavored consumer products include:
seasonings or dressings, such as soups (stock), bouillon cubes (savory cube), powder mixes, dressing oils, sauces (such as dressing, barbecue sauce, dressing, gravy or sweet and/or sour sauce), salad dressing or mayonnaise;
meat products, such as poultry, beef or pork meat products, seafood, surimi or fish sausages;
soups, such as broth, cream, chicken or beef, or tomato or asparagus;
carbohydrate products such as instant noodles, rice, pasta, potato or french fries, noodles, pizza, tortillas, curls;
dairy or fat products such as spreads, cheeses, low or normal fat margarines, butter/margarine mixtures, butter, peanut butter, shortening, processed or flavoured cheese;
savory products such as snacks, biscuits (such as potato chips or chips) or egg products, potato/corn tortilla chips, microwave oven popcorn, nuts, pretzels, rice cakes and the like;
confectionery (confectioneries), such as baked goods (e.g. tara or cake), confectionery (e.g. sweets, candies, sweet nuts, chocolates, chewing and bubble gums, preserves, candy pieces, sugar-free candies) or chocolate candies;
oral care products such as toothpaste, mouthwash, dental care products (such as denture adhesives), mouthwashes, mouth sprays, tooth powders, tooth gels or dental floss;
artificial food (animation product), such as dairy products (e.g. modified cheese made of oil, fat and thickener) or seafood or meat (e.g. vegetarian meat substitutes, vegetarian hamburgers) or the like;
a pet or animal food; or
Beverages, such as hot beverages (e.g. tea), soft drinks including carbonated soft drinks, alcoholic beverages, ready-to-drink or powdered soft drinks.
Particularly preferred flavored consumer products in which the compositions of the present invention are useful include confectionery and oral care products, preferably oral care products.
Some of the flavoured consumer products mentioned above may represent an aggressive medium for the composition of matter of the invention and may therefore need to be protected from premature decomposition, for example by encapsulation or by chemically binding them to another chemical substance suitable for releasing the composition of matter of the invention upon exposure to a suitable external stimulus, such as an enzyme, light, heat or a change in pH.
The proportions in which the composition of matter of the invention can be incorporated into the various aforementioned products vary within wide limits. These values depend on the nature and the desired organoleptic effect of the article to be flavored and on the nature of the co-ingredients in a given base, when the composition according to the invention is mixed with perfuming or flavoring ingredients, solvents or additives commonly used in the art.
For example, in the case of flavoring compositions, typical concentrations of the composition of matter of the present invention are on the order of 0.001ppm to 1000ppm by weight, based on the weight of the composition into which it is incorporated. In the case of flavored consumer products, typical concentrations of the compositions of matter of the present invention are on the order of 0.001ppm to 1000ppm by weight, more preferably 0.5ppm to 500ppm, most preferably 1 to 350ppm, based on the weight of the consumer product into which they are incorporated.
The composition of matter of the invention can also be used as perfuming ingredient. The present invention therefore relates to a composition comprising at least one compound of the formula (I) and at least one C1-6Use of a composition of matter of linear or branched alkyl lactate as perfuming ingredient. In other words, it concerns a method or a process for imparting, enhancing, improving or modifying the odor properties of a perfuming composition or of a perfumed article or surface, which method comprises adding to said composition or article an effective amount of a composition of matter according to the invention, for example to impart typical notes thereto.
By "use of a composition of matter", it must also be understood herein that the composition comprises at least one compound of formula (I) and at least one C1-6Linear or branched alkyl lactate, and can be advantageously used in the perfumery industry.
Said compositions, which can in fact be advantageously used as perfuming ingredients, are also an object of the present invention.
Therefore, another object of the present invention is a perfuming composition comprising:
i) at least one compound as defined above comprising at least one compound of formula (I) and at least one C1-6A composition of matter of linear or branched alkyl lactate;
ii) at least one ingredient selected from the group consisting of a fragrance carrier, a perfuming co-ingredient, and mixtures thereof; and
iii) optionally, at least one flavor adjuvant.
By "perfume carrier" is meant here a material that is practically neutral from the perfume point of view; i.e. without significantly altering the organoleptic properties of the perfuming ingredients. The carrier may be a liquid or a solid.
As liquid carrier there may be mentioned, as non-limiting examples, emulsifying systems, i.e. solvent and surfactant systems, or solvents commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery is not exhaustive. However, mention may be made, as non-limiting examples, of solvents such as butanediol or propylene glycol, glycerol, dipropylene glycol and its monoethers, 1,2, 3-propanetriester triacetate, dimethyl glutarate, dimethyl adipate, 1, 3-diacetoxypropan-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2- (2-ethoxyethoxy) -1-ethanol, triethyl citrate or mixtures thereof, which are most commonly used. For compositions comprising both a fragrance carrier and a perfuming co-ingredient, other suitable fragrance carriers than those specified above may also be ethanol, a water/ethanol mixture, limonene or other terpenes, isoparaffins, e.g. under the trademark Resilience TM, e.g. an isoalkaneThose known per se (source: Exxon Chemical), or glycol ethers and glycol ether esters, e.g. under the trade mark
By solid carrier is meant a material, to which a perfuming composition or some of the ingredients of a perfuming composition can be chemically or physically associated. Typically, such solid carriers are used to stabilize the composition, or to control the evaporation rate of the composition or certain ingredients. Solid carriers are currently used in the art, and the skilled person knows how to achieve the desired effect. However, as non-limiting examples of solid carriers there may be mentioned absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood-based materials, organic or inorganic gels, clays, gypsum, talc or zeolites.
As other non-limiting examples of solid carriers, encapsulating materials may be cited. Examples of such materials may include wall-forming materials and plasticizing materials, such as monosaccharides, disaccharides or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinyl alcohols, proteins or pectins, or as described in references such as H.Scherz, Hydrokolloides: Stabilisatoren, Dickungs-und Geliermentil in Lebensmittel, Band2der Schrieftereue Lebensmittemel,
As non-limiting examples of solid carriers, mention may be made in particular of core-shell capsules using resins of the aminoplast, polyamide, polyester, polyurea or polyurethane type or mixtures thereof, all of which are well known to those skilled in the art, by phase separation processes initiated by the use of polymerization, interfacial polymerization, coacervation, and the like techniques or these techniques together, all of which have been described in the prior art, and optionally in the presence of polymeric stabilizers or cationic copolymers.
The resins may be produced by the polycondensation of aldehydes (such as formaldehyde, 2-dimethoxyacetaldehyde, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with amines such as urea, benzoguanamine, glycoureido, melamine, methylolmelamine, methylated methylolmelamine, guanazol and the like and mixtures thereof. Alternatively, a preformed resin alkylation (alkylola) may be usedted) polyamines, e.g. under the trade mark
Other resins are prepared by reacting a polyol such as glycerol with a polyisocyanate such as a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate or xylylene diisocyanate or a biuret of hexamethylene diisocyanate, or a trimer of xylylene diisocyanate with trimethylolpropane (under the trade name
Some research literature relating to the encapsulation of fragrances by polycondensation of amino resins, i.e. melamine-based resins, with aldehydes includes articles such as Acta Polymerica,1989, vol.40, pages 243,325 and 683 and 1990, vol.41, page 91, published by k. These articles have described various parameters affecting the preparation of such core-shell microcapsules according to prior art processes, which are also further detailed and exemplified in the patent literature. US 4'396'670 to Wiggins TeapGroup Limited is a related early example of the latter. Since then, many other authors have enriched the literature in this area, and it is not possible here to cover all published developments, but the general knowledge of encapsulation techniques is of great importance. More recent targeted publications, which also relate to suitable uses of such microcapsules, e.g.Journal of Microencapsidation, 2002, vol.19, pages559-569, International patent publication WO01/41915 or S, by H.Y.Lee et al.
By "perfuming co-ingredient", it is meant here a compound which is used in a perfuming formulation or composition to impart a hedonic effect. In other words, such a co-ingredient to be considered as being a perfuming co-ingredient must be recognized by a person skilled in the art as being capable of imparting or modifying in an active or pleasant way the odor of a composition, and not just as having an odor. Said perfuming co-ingredient is not a compound of formula (I).
The nature and type of the perfuming co-ingredients present in the perfuming compositions do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect. In general, these perfuming co-ingredients belong to different chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and can be of natural or synthetic origin.
In particular, mention may be made of the perfuming co-ingredients commonly used in perfumery formulations, such as:
-aldehyde fragrance component: decanal, dodecanal, 2-methylundecanal, 10-undecenal, octanal and/or nonenal;
-aromatic herbs ingredients including eucalyptus oil, camphor, eucalyptol, menthol and/or α -pinene;
-a balm component: coumarin, ethyl vanillin and/or vanillin;
-citrus flavour components: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, auraptene, limonene, 1-p-menthen-8-yl acetate and/or 1,4(8) -p-menthadiene;
floral constituents methyl dihydrojasmonate, linalool, citronellol, phenethyl alcohol, 3- (4-tert-butylphenyl) -2-methylpropanal, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4 (2H) -pyranol, β -ionone, methyl 2- (methylamino) benzoate, (E) -3-methyl-4- (2,6, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one, hexyl salicylate, 3, 7-dimethyl-1, 6-nonadien-3-ol, 3- (4-isopropylphenyl) -2-methylpropanal, tricyclodecenyl acetate, geraniol, p-menth-1-en-8-ol, 4- (1, 1-dimethylethyl) -1-cyclohexyl acetate, 1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, pentyl salicylate, methyl homodihydrojasmonate, 3-methyl-5-phenyl-1-phenylethyl acetate, 1, 4-dimethyldecyl acetate, 2-methylpentyl acetate, 2-methylpropyl methacrylate, 2-isopropyl methacrylate, 2-ethyl methacrylate, 3-isopropyl methacrylate, 3-methyl-2-ethyl methacrylate, 3-1, 3-ethyl methacrylate, 4-methyl-2-methyl-2-butyl methacrylate, 4-ethyl methacrylate, 4-isopropyl methacrylate, 4-methyl-2-ethyl methacrylate, 4-isopropyl methacrylate, 4-methyl-2-ethyl methacrylate, 4-isopropyl methacrylate, 4-2-isopropyl methacrylate, 4-methyl-2-methyl-2-methyl-ethyl methacrylate, 4-ethyl;
-fruit aroma components: gamma-undecalactone, 4-decalactone, ethyl 2-methyl-valerate, hexyl acetate, ethyl 2-methylbutyrate, gamma-nonalactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1, 3-dioxolane-2-acetate and/or diethyl 1, 4-cyclohexanedicarboxylate;
-green components: 2, 4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styryl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z) -3-hexen-1-ol and/or 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one;
-a musk component: 1, 4-dioxa-5, 17-cyclopentadecanedione, pentadecenolide, 3-methyl-5-cyclopentadecen-1-one, 1,3,4,6,7, 8-hexahydro-4, 6,6,7,8, 8-hexamethylcyclopenta [ G ] -2-benzopyran, propionic acid (1S,1'R) -2- [1- (3',3 '-dimethyl-1' -cyclohexyl) ethoxy ] -2-methylpropyl ester, pentadecanolide and/or propionic acid (1S,1'R) - [1- (3',3 '-dimethyl-1' -cyclohexyl) ethoxycarbonyl ] methyl ester;
-a woody component: 1- (octahydro-2, 3,8, 8-tetramethyl-2-naphthyl) -1-ethanone, patchouli oil, terpene fractions of patchouli oil, (1'R, E) -2-ethyl-4- (2',2',3' -trimethyl-3 '-cyclopenten-1' -yl) -2-buten-1-ol, 2-ethyl-4- (2,2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, cedar wood ketone, 5- (2,2, 3-trimethyl-3-cyclopentenyl) -3-methylpentan-2-ol, 1- (2,3,8, 8-tetramethyl-1, 2,3,4,6,7,8,8 a-octahydronaphthalen-2-yl) ethan-1-one and/or isobornyl acetate;
other ingredients (e.g. amber, pink, spicy or watery): dodecahydro-3 a,6,6,9 a-tetramethylnaphtho [2,1-b ] furan and any of its stereoisomers, piperonal, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3- (1, 3-benzodioxol-5-yl) -2-methylpropionaldehyde, and/or 3- (3-isopropyl-1-phenyl) butanal.
The perfuming co-ingredients according to the invention may not be limited to the above-mentioned ingredients, and many other such co-ingredients are in any case listed in the literature references, such as s.arctander, Perfume and flavour Chemicals,1969, Montclair, New Jersey, USA or newer versions thereof, or other works of similar nature, as well as a large body of patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.
By "perfumery adjuvant" we mean here an ingredient capable of imparting additional benefits such as colour, specific light fastness, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfuming compositions is not exhaustive, but it must be mentioned that said ingredients are well known to the person skilled in the art. Specific non-limiting examples may be listed as follows: viscosity agents (e.g., surfactants, thickeners, gelling and/or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, heat/light stabilizers or buffers or chelating agents, such as BHT), colorants (e.g., dyes and/or pigments), preservatives (e.g., antibacterial or antimicrobial or antifungal or anti-irritant agents), abrasives, skin cooling agents, fixatives, insect repellents, ointments, vitamins and mixtures thereof.
It is understood that the person skilled in the art is fully capable of designing optimal formulations for the desired effect, simply by applying the standard knowledge in the field and by mixing the above-mentioned components of the perfuming composition by trial and error.
In addition to a composition comprising at least one compound of formula (I), at least one C1-6Linear or branched alkyl lactate, at least one perfumery carrier, at least one perfuming co-ingredient and optionally at least one perfumery adjuvant, in addition to a perfuming composition consisting of at least one compound of formula (I), at least one C1-6The inventive composition of linear or branched alkyl lactate and at least one fragrance carrier also represents a particular embodiment of the invention.
According to any of the above embodiments, the perfuming composition of the invention may be a shampoo, a colorant, a hair spray, a color care product, a hair styling product, a dental care product, a disinfectant, a personal care product, a skin cream or lotion, a vanishing cream, a body balm or antiperspirant, a depilatory, a tanning or sunscreen product, a nail product, a skin cleanser, a cosmetic product, a perfumed soap, a bath mousse, a bath or shower gel, a foot/hand care product, a hygiene product, an air freshener, a "ready to use" powdered air freshener, a mould remover, a furniture care product, a wipe, a dish detergent or hard-surface detergent, a leather care product. Preferably, the perfuming composition of the invention can be in the form of an air freshener.
Furthermore, the composition of matter of the invention can also be advantageously used in all the fields of modern perfumery, i.e. fine or functional perfumery, to actively impart or modify the odor of consumer products to which said compound (I) is added. Therefore, another object of the present invention is a perfumed consumer product comprising at least one composition of matter according to the invention as defined above.
The composition of matter of the invention can be added as such or as part of the perfuming composition of the invention.
For the sake of clarity, "perfumed consumer product" means a consumer product which delivers at least one pleasant perfuming effect to the surface or space (e.g. skin, hair, fabric or household surface) to which it is applied. In other words, a perfumed consumer product according to the invention is a perfumed consumer product comprising the functional formulation and optionally additional benefit agents corresponding to the desired consumer product, and an olfactory effective amount of at least one compound of the invention. For the sake of clarity, said perfumed consumer product is a non-edible product.
The nature and type of the ingredients of perfumed consumer product do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the nature and the desired effect of said product.
Non-limiting examples of suitable perfumed consumer products include perfumes, such as fine perfumes, spread perfumes (splash) or light perfumes (eau de perfume), colognes or shave or after-shave lotions; fabric care products such as liquid or solid detergents, fabric softeners, liquid or solid fragrance enhancers, fabric refreshers, ironing waters, papers, bleaches, carpet cleaners, curtain care products; body care products, such as hair care products (e.g., shampoos, colorants or hair gels, color care products, hair styling products, dental care products), disinfectants, personal care products; cosmetic preparations (e.g. skin creams or lotions, vanishing creams, body scents or antiperspirants (e.g. sprays or beads), depilatories, tanning agents, sun or after-sun products, nail products, skin cleansing products, cosmetics); or a skin care product (e.g. a soap, bath mousse, oil or gel, or a hygiene product or foot/hand care product); air care products such as air fresheners or "ready-to-use" powder air fresheners, which can be used in home spaces (rooms, refrigerators, cabinets, shoes or cars) and/or public spaces (halls, hotels, malls, etc.); or a home care product, such as a mould remover, a furniture care agent, a wipe, a dishwashing detergent or a hard surface (e.g. floor, bathroom, sanitaryware or window) detergent; leather care products; automotive care products such as polishes, waxes or plastic cleaners.
Some of the above mentioned perfumed consumer products may represent an aggressive medium of the composition of matter of the invention and may therefore need to be protected from premature decomposition, e.g. by encapsulation or by chemically binding them to another chemical substance suitable for releasing the ingredients of the invention upon exposure to a suitable external stimulus, such as an enzyme, light, heat or a change in pH.
The proportions in which the composition of matter of the invention can be incorporated into the various aforementioned products vary within wide limits. These values, when the composition of matter according to the invention is mixed with perfuming co-ingredients, solvents or additives commonly used in the art, depend on the nature of the article to be perfumed and on the desired organoleptic effect as well as on the nature of the co-ingredients in a given base.
For example, in the case of perfuming compositions, typical concentrations are in the order of 0.001ppm to 1000ppm by weight, or even more, of the composition of matter of the invention, based on the weight of the composition into which it is incorporated. In the case of perfumed consumer products, typical concentrations of the composition of matter of the invention are of the order of 0.01ppm to 500ppm by weight, or even higher, based on the weight of the consumer product into which it is incorporated.
Another object of the present invention is a process for preparing a composition of matter as defined above, comprising the following steps:
a) preparing a compound of formula (I) as defined in claim 1 by reacting a compound of formula (II) with a compound of formula (III),
wherein R is1Represents optionally one or two C1-3Alkyl or alkoxy or phenyl substituted with one or two halo; x represents hydroxy, C1-10An alkoxy group or a chlorine atom;
wherein R is2And R3Independently of one another, represents a heterocyclic radical comprising 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, optionallyBy one or two C1-3Alkyl substitution;
b) crystallizing the reaction mixture obtained in step a);
c) filtering the solution of the crystalline product obtained in step b);
d) drying the crystalline product obtained in step c); and
e) dissolving the dried crystalline product obtained in step d) in C1-6Linear or branched alkyl lactate.
For clarity, the term "crystalline" is meant to have its normal meaning in the art. That is, the reaction mixture is subjected to conditions favorable for crystal growth.
According to any of the above embodiments, R1、R2And R3Have the same meaning as defined above.
According to any of the above embodiments, step a) is an amidation reaction. The conditions to be employed in order to obtain the desired product are well known to those skilled in the art. Non-limiting examples of suitable reagents/conditions for carrying out step a) include thermal conditions, the presence of a base or a lewis acid. The choice of reaction conditions depends on the nature of the substrate and the person skilled in the art is able to select the most convenient conditions in each case in order to optimize the reaction. Preferably, step a) is carried out by heating the reaction mixture at a temperature higher than 150 ℃ in the presence of a base or under thermal conditions. Even more preferably, step a) is carried out in the presence of a base. Non-limiting examples of suitable bases include amine bases such as pyridine, trimethylamine, lutidine, N-diisopropylethylamine or 1, 8-diazabicyclo [5.4.0] undec-7-ene or alkali metal alkoxides, carbonates or hydroxides. Preferably, the base may be an alkoxide, carbonate or hydroxide of an alkali metal. Even more preferably, the base may be an alkali metal alkoxide. Even more preferably, the base may be a methoxide, ethoxide, propoxide, butoxide or tert-butoxide of sodium or potassium. Even more preferably, the base may be sodium or potassium methoxide.
According to any one of the preceding embodiments, X represents C1-10An alkoxy group. Preferably, X may represent C1-5An alkoxy group. Even more preferably, X may represent C1-3An alkoxy group. Even more preferably, X may be methoxy, ethoxy or propoxy, even ethoxy.
The compounds of formulae (II) and (III) may be prepared according to methods known in the art or as reported in WO 2012/061698.
Step a) may be carried out in the presence or absence of a solvent. Any solvent stream of this reaction type can be used for the purposes of the present invention when a solvent is required or used for practical reasons. Non-limiting examples include methanol, ethanol, cyclohexane, THF, Me-THF, MTBE, DME, Et2O, toluene, butanone, dichloromethane and dodecane. The choice of solvent depends on the nature of the compounds of the formulae (II) and (III) and/or the base, and the person skilled in the art is able to select the solvent most conveniently in each case to optimize the reaction.
According to any one of the embodiments of the invention, the process of the invention is carried out at a temperature of from 20 ℃ to 250 ℃. In particular, the temperature is in the range of 30 ℃ to 150 ℃. Of course, the person skilled in the art will also be able to select the preferred temperature depending on the melting and boiling points of the starting and final products and the time required for the reaction or conversion.
According to any of the above embodiments, the crystallization of step b) is carried out by slowly cooling the reaction mixture at room temperature over a period of more than 5 hours, preferably more than 10 hours.
According to any of the above embodiments, steps c) to e) of the process of the invention are carried out in the same apparatus; that is, an agitation type filter dryer, also called a Nucha vacuum filter dryer, a filter dryer or a Nutsche agitation type dryer. Filtration, drying and dissolution in the same apparatus may reduce the handling of the resulting compound of formula (I).
The compound of formula (I) obtainable by performing steps a) to d) is in crystalline form it has surprisingly been found that the compound of formula (I) can crystallize in more than one type of three-dimensional crystalline structure in other words, several polymorphs of the compound of formula (I), in particular N- (1H-pyrazol-3-yl) -N- (thiophen-2-ylmethyl) -2- (p-tolyloxy) acetamide, are obtained, it is well known that polymorphs of a particular organic compound have different physical properties, such as solubility and hygroscopicity, due to their unique three-dimensional crystalline structure, however, it is generally not possible to predict whether a particular organic compound will form different crystalline forms, let alone predict the structure and properties of the crystalline form itself, it is found that a new crystal or polymorph form of a useful compound can provide a new opportunity for improving the overall properties of the final product, such as a flavored or flavored consumer product, it enlarges the library which formulation scientists can be used for designing, it is possible to obtain, according to the method of the invention, the compound N- (1H-3-2-yl) -2- (p-tolyloxy) -23, 18, 24, 18, 17, 18, 17, and thus the most useful compounds.
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