阅读说明：本技术 作为香精成分的烯基硫代碳酸酯 (Alkenyl thiocarbonates as perfume ingredients ) 是由 A·考乌尔斯 B·克兰 于 2018-05-09 设计创作，主要内容包括：提供了新的式(I)的烯基硫代碳酸酯、其制备方法及其作为香精和香料的用途。还提供了包含所述新的式(I)的烯基硫代碳酸酯的香精和香料组合物和可食用产品,尤其是咖啡产品。<Image he="420" wi="700" file="DDA0002260107760000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(Novel alkenyl thiocarbonates of formula (I), processes for their preparation and their use as perfumes and fragrances are provided. Flavour and fragrance compositions and edible products, especially coffee products, comprising the novel alkenyl thiocarbonates of formula (I) are also provided.)

1. A compound of formula (I)

Wherein

n is 1 or 2;

m is 1, 2 or 3;

R¹is alkyl or aryl; and is

R²、R³、R⁴Independently represents hydrogen or an alkyl group.

2. The compound of claim 1 selected from the group consisting of O-ethyl S- (3-methylbut-2-en-1-yl) thiocarbonate; o-ethyl S- (3-methylbut-3-en-1-yl) thiocarbonate; (E) -S- (but-2-en-1-yl) O-ethylthiocarbonate; s- (but-3-en-1-yl) O-ethylthiocarbonate; s-allyl O-ethyl thiocarbonate; o-ethyl S-geranyl thiocarbonate; o-ethyl S-neryl thiocarbonate; and O-ethyl S-farnesyl thiocarbonate.

3. Use of a compound according to claim 1 in an edible product.

4. The compound of claim 1, wherein R¹Methyl, ethyl, propyl, isobutyl, tert-butyl, phenyl or benzyl).

5. The compound of claim 1, wherein R²、R³、R⁴Selected from methyl, ethyl or propyl.

6. A perfume composition comprising:

a compound of formula (I)

Wherein

n is 1 or 2; m is 1, 2 or 3; r¹Is alkyl or aryl; and R is²、R³、R⁴Independently represents hydrogen or alkyl; and

at least one perfume ingredient.

7. The perfume composition according to claim 6, wherein the compound of formula (I) is selected from O-ethyl S- (3-methylbut-2-en-1-yl) thiocarbonate; o-ethyl S- (3-methylbut-3-en-1-yl) thiocarbonate; (E) -S- (but-2-en-1-yl) O-ethylthiocarbonate; s- (but-3-en-1-yl) O-ethylthiocarbonate; s-allyl O-ethyl thiocarbonate; o-ethyl S-geranyl thiocarbonate; o-ethyl S-neryl thiocarbonate; and O-ethyl S-farnesyl thiocarbonate.

8. The perfume composition of claim 6 wherein the compound of formula (I) is present at a level of from about 0.005ppm to about 5.0ppm by weight of the composition.

9. The perfume composition of claim 6 wherein the compound of formula (I) is present at a level of from about 0.01ppm to about 1.0ppm by weight of the composition.

10. The perfume composition according to claim 6, further comprising a carrier material.

11. A beverage product comprising:

a compound selected from O-ethyl S- (3-methylbut-2-en-1-yl) thiocarbonate; o-ethyl S- (3-methylbut-3-en-1-yl) thiocarbonate; (E) -S- (but-2-en-1-yl) O-ethylthiocarbonate; s- (but-3-en-1-yl) O-ethylthiocarbonate; s-allyl O-ethyl thiocarbonate; o-ethyl S-geranyl thiocarbonate; o-ethyl S-neryl thiocarbonate; and O-ethyl S-farnesylthiocarbonate;

a perfume composition; and

and (4) a product substrate.

12. The beverage product of claim 11, wherein the compound is present at a level of about 0.001ppb to about 1.0ppb by weight of the beverage product.

13. The beverage product of claim 11, wherein the compound is present at a level of about 0.002ppb to about 0.5ppb by weight of the beverage product.

14. The beverage product of claim 11, wherein the compound is present at a level of about 0.003ppb to about 0.3ppb by weight of the beverage product.

15. The beverage product of claim 11, wherein the flavor composition comprises at least one flavor component.

16. The beverage product of claim 11, wherein the flavor composition comprises a carrier material.

17. The beverage product of claim 11, wherein the product is coffee.

Technical Field

The present disclosure relates to the use of thiocarbonates (carbonothioates) as perfumes and fragrances. More specifically, the disclosure relates to the use of O-alkyl S-hydroxyalkenyl thiocarbonates as perfumes and fragrances.

Background

The flavor and fragrance industry continues to be interested in new ingredients that can enhance, improve or modify the flavor characteristics of consumer products.

The aroma of edible products such as foods and beverages consists of two parts: aroma and taste. In general, what is provided by the olfactory epithelium in the nasal cavity is called "aroma", while the term "taste" is generally used to describe the sensory impact perceived by the mouth, particularly the tongue.

Surprisingly, the inventors have found that by mixing an O-alkyl S-hydroxyalkenyl thiocarbonate of formula (I) as defined below into an edible product, the flavour of the edible product can be significantly improved.

It was found that the flavour of a product containing a compound of formula (I) as defined below is more intense and/or lasts longer than a product not containing said compound of formula (I). These properties are maintained under processing conditions, such as heating from about 75 ℃ to about 150 ℃, which makes the compounds of formula (I) particularly suitable for processed foods and beverages, such as instant coffee and powdered coffee beverages.

Summary of The Invention

In one embodiment, compounds of formula (I) are provided:

wherein n is 1 or 2; m is 1, 2 or 3; r¹Is alkyl or aryl; and R is²、R³、R⁴Independently represents hydrogen or an alkyl group.

In another embodiment, the perfume composition comprises a compound of formula (I)

Wherein n is 1 or 2; m is 1, 2 or 3; r¹Is alkyl or aryl; and R is²、R³、R⁴Independently represents hydrogen or alkyl; and at least one perfume ingredient.

In another embodiment, a beverage product comprises: a compound selected from O-ethyl S- (3-methylbut-2-en-1-yl) thiocarbonate; o-ethyl S- (3-methylbut-3-en-1-yl) thiocarbonate; (E) -S- (but-2-en-1-yl) O-ethylthiocarbonate; s- (but-3-en-1-yl) O-ethylthiocarbonate; s-allyl O-ethyl thiocarbonate; o-ethyl S-geranyl thiocarbonate; o-ethyl S-neryl thiocarbonate; and O-ethyl S-farnesylthiocarbonate; a perfume composition; and a product substrate.

These and other features, aspects, and advantages of particular embodiments will become apparent to those skilled in the art upon reading the present disclosure.

Detailed Description

The following text sets forth a broad description of many different embodiments of the disclosure. The description is to be construed as exemplary only and does not describe every possible embodiment since describing every possible embodiment would be impractical, if not impossible. It will be understood that any feature, characteristic, ingredient, composition, component, product, step or method described herein may be deleted, combined, or substituted in whole or in part for any other feature, characteristic, ingredient, composition, component, product, step or method described herein. Numerous alternative embodiments could be implemented, using either current technology or technology developed after the filing date of this patent, which would still fall within the scope of the claims. All publications and patents cited herein are incorporated herein by reference.

In accordance with the present disclosure, there are provided compounds of formula (I)

Wherein

n is 1 or 2;

m is 1, 2 or 3;

R¹is alkyl or aryl (e.g. methyl, ethyl, propyl, iso-propyl)Butyl, tert-butyl, phenyl or benzyl); and is

R²、R³、R⁴Independently represents hydrogen or an alkyl group (e.g., methyl, ethyl or propyl).

The compounds of formula (I) contain several chiral centers and may therefore exist as mixtures of stereoisomers, or they may be resolved into isomerically pure forms. Resolving stereoisomers adds to the complexity of preparation and purification of these compounds and so it is preferred for economic reasons only that the compounds are used simply as their mixture of stereoisomers. However, if it is desired to prepare a single stereoisomer, this may be achieved according to methods known in the art, such as preparative HPLC and GC, crystallization or stereoselective synthesis.

In particular embodiments, the compound of formula (I) is selected from:

o-ethyl S- (3-methylbut-2-en-1-yl) thiocarbonate;

o-ethyl S- (3-methylbut-3-en-1-yl) thiocarbonate;

(E) -S- (but-2-en-1-yl) O-ethylthiocarbonate;

s- (but-3-en-1-yl) O-ethylthiocarbonate;

s-allyl O-ethyl thiocarbonate;

o-ethyl S-geranyl thiocarbonate;

o-ethyl S-neryl thiocarbonate; and

o-ethyl S-farnesyl thiocarbonate.

The compounds of formula (I) may be used alone or in combination with other substances useful for the desired purpose, such as perfumes or fragrances. In one embodiment, the compounds of formula (I) may be combined with other fragrances and/or perfumes selected from the wide range of natural and synthetic molecules currently available, such as essential oils and extracts, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles.

Accordingly, in a further embodiment there is provided a perfume composition comprising a compound of formula (I) and at least one additional perfume ingredient.

In another embodiment, the compound of formula (I) may be mixed with one or more ingredients or excipients conventionally used in conjunction with flavors or fragrances for perfuming/flavoring applications, such as carrier materials and other adjuvants commonly used in the art, such as solvents (e.g. dipropylene glycol (DPG), isopropyl myristate (IPM), triethyl citrate (TEC), ethanol, Propylene Glycol (PG), triacetin and benzyl alcohol the compounds of formula (I) may be dissolved or dispersed in a carrier material such as a fat or coated with maltose-dextrin, gelatin, gum arabic etc. (enrobed).

In a further embodiment, there is provided a fragrance application comprising a compound of formula (I) and a product base.

Particularly suitable flavouring applications for the compounds of formula (I) are foods and beverages, such as dry, canned, frozen and instant soups, ready-to-eat meals, croquettes, sauce pieces, soup powder pieces, baking grease, margarine, bread, cakes and instant beverages prepared with hot water, such as instant coffee and powdered coffee beverages, beer, soft drinks, flavoured tea and dairy products. This list of products is given as an illustration and is not to be construed as limiting in any way.

"product substrate" as used herein in connection with a fragrance application refers to an edible product that does not contain a compound of formula (I) as defined above.

As used herein, "edible product" refers to products such as foods and beverages, or personal care products that are intended to be introduced into the oral cavity of a human or animal and left there for a period of time before being digested or removed from the mouth. These products include compositions in their processed, partially processed, or unprocessed state.

The compound of formula (I) may be present in the article in an amount of from about.001 ppb to about 1.0ppb, in another embodiment from about.002 ppb to about 0.5ppb, and in another embodiment from about.003 ppb to about 0.3ppb, by weight of the article.

If used in a perfume composition, the compound of formula (I) may be present in an amount of from about 0.005ppm to about 5.0ppm, in another embodiment from about.01 ppm to about 1.0ppm, based on the perfume composition.

In another embodiment, the compounds of formula (I) may be used in a wide range of fragrance applications, such as any of the fine and functional fragrance fields, such as perfumes, household products, laundry products, body care products and cosmetics.

If used in fragrance applications, the compounds of formula (I) may be present in an amount of about 1 to 30ppm, based on the fragrance application. However, these values are given by way of example only, as experienced perfumers may also achieve effects or may create new accords with lower or higher concentrations.

The compounds of formula (I) may be applied in a product base by mixing the compounds or a flavour/fragrance composition comprising said compounds with the product base, and/or they may be entrained with the entraining material in an early step and then mixed with the consumer product base.

The compounds of formula (I) can be prepared as shown in scheme 1 under conditions known to the skilled person. Further details regarding the reaction conditions are provided in the examples.

Scheme 1:

n; m; r1; r2; r3 and R4 have the same meaning as given in formula (I) above.

In one embodiment, O-ethyl S- (3-methylbut-2-en-1-yl) thiocarbonate may be prepared as follows:

when n and m are 1; r¹Is ethyl; r²Is hydrogen; r3 is methyl and R4 is hydrogen.

In another embodiment, O-ethyl S-geranyl thiocarbonate may be prepared as follows:

when n is 1; m is 2; r1 is ethyl; r2 is hydrogen; r3 is methyl and R4 is hydrogen.

In another embodiment, O-ethyl S-farnesyl thiocarbonate can be prepared as follows:

when n is 1; m is 3; r1 is ethyl; r2 is hydrogen; r3 is methyl and R4 is hydrogen.