Methods of modifying or imparting taste using organic compounds

Patent metadata

Field	Value
Publication number	US-10178875-B2
Application number	US-201414901279-A
Country	US
Kind code	B2
Filing date	Jul 1, 2014
Priority date	Jul 1, 2013
Publication date	Jan 15, 2019
Grant date	Jan 15, 2019

Abstract

A method of imparting to, or modifying in, a comestible product, umami taste, including the addition to a comestible product base of at least one compound of formula (I)

wherein one of X 1 , X 2 , or X 3 is selected from the group consisting of S, N and O and the remaining two are CH 2 ; and A is selected from

in which R 1 , R 2 , R 3 , R 4 R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, COOR 7 , in which R 7 is selected from linear or branched C 1 -C 7 alkyl, and CONR 8 R 9 , in which R 8 and R 9 are independently selected from hydrogen and straight or branched C 1 -C 4 alkyl; or any two adjacent substituents R 2 -R 6 together form a ring of 5 or 6 members; and n is 1 or 0.

First claim

The invention claimed is:

1. A method of imparting to, or modifying in, a comestible product, umami taste comprising
the addition to a comestible product base of at least one compound of formula (I)

wherein one of X 1 , X 2 , or X 3 is selected from the group consisting of S, N and O and the remaining two are CH 2 ; and A is selected from

in which R 2 , R 3 , R 4 , R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, COOR 7 , in which R 7 is selected from linear C 1 -C 7 alkyl, branched C 3 -C 7 alkyl, and CONR 8 R 9 , in which R 8 and R 9 are independently selected from hydrogen, straight C 1 -C 4 alkyl, and branched C 3 -C 4 alkyl; or any two adjacent substituents R 2 -R 6 together form a ring of 5 or 6 members; and n is 1 or 0.

2. The method according to claim 1 , in which one of X 1 , X 2 , or X 3 is S and the remaining two are CH 2 .

3. The method according to claim 1 , in which X 1 is S, and, X 2 and X 3 are CH 2 .

4. The method according to claim 1 , in which X 2 is S, and, X 1 and X 3 are CH 2 .

5. The method according to claim 1 , in which A is

in which R 2 , R 3 , R 4 , R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, COOR 7 , in which R 7 is selected from linear C 1 -C 7 alkyl, branched C 3 -C 7 alkyl, and CONR 8 R 9 , in which R 8 and R 9 are independently selected from hydrogen, straight C 1 -C 4 alkyl, and branched C 3 -C 4 alkyl; or any two adjacent substituents R 2 -R 6 together form a ring of 5 or 6 members; and n is 1 or 0.

6. The method according to claim 1 , in which X 1 is S, and, X 2 and X 3 are CH 2 , and A is

in which R 2 , R 3 , R 4 , R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, and COOR 7 , in which R 7 is selected from linear C 1 -C 7 alkyl and branched C 3 -C 7 alkyl, and n is 0.

7. The method according to claim 1 , in which the compound of formula (I) is selected from the group consisting of: 2-(2-(Phenylthio)ethyl)pyridine, 2-(2-(Phenylthio)ethyl)pyridine hydrochloride, Methyl 4-((2-(pyridin-2-yl)ethyl)thio) benzoate hydrochloride, 2-(2-(p-tolylthio)ethyl)pyridine hydrochloride, 2-(2-(o-tolylthio) ethyl)pyridine hydrochloride, 4-((2-(pyridin-2-yl)ethyl)thio)phenol, 2-((2-(pyridin-2-yl) ethyl)thio)phenol, 2-(2-((3-methoxyphenyl)thio)ethyl)pyridine, Methyl 2-((2-(pyridin-2-yl)ethyl)thio)benzoate hydrochloride, 3-((2-(pyridin-2-yl)ethyl)thio)phenol, 2-(2-(benzylthio)ethyl)pyridine, 2-(2-(m-Tolylthio)ethyl)pyridine hydrochloride, and 2-(2-((4-Methoxyphenyl)-thio)ethyl)pyridine hydrochloride.

8. The method according to claim 1 , in which the compound of formula (I) is a salt.

9. The method according to claim 8 , in which the compound of formula (I) is in the form of hydrochloride salt.

10. A method of imparting to, or modifying in, a flavour composition or comestible product, salt taste, comprising the addition to said flavour composition or comestible product of at least one compound of formula (I)

wherein one of X 1 , X 2 , or X 3 is selected from the group consisting of S, N and O and the remaining two are CH 2 ; and A is selected from

in which R 2 , R 3 , R 4 , R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, COOR 7 , in which R 7 is selected from linear C 1 -C 7 alkyl, branched C 3 -C 7 alkyl, and CONR 8 R 9 , in which R 8 and R 9 are independently selected from hydrogen, straight C 1 -C 4 alkyl, and branched C 3 -C 4 alkyl; or any two adjacent substituents R 2 -R 6 together form a ring of 5 or 6 members; and n is 1 or 0.

11. A method of imparting to, or modifying in, a flavour composition or comestible product, a fruity, green, green pepper, tomato and/or bell pepper aroma, comprising the addition to said flavour composition or comestible product of at least one compound of formula (I)

wherein one of X 1 , X 2 , or X 3 is selected from the group consisting of S, N and O and the remaining two are CH 2 ; and A is selected from

in which R 2 , R 3 , R 4 R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, COOR 7 , in which R 7 is selected from linear C 1 -C 7 alkyl, branched C 3 -C 7 alkyl, and CONR 8 R 9 , in which R 8 and R 9 are independently selected from hydrogen, straight C 1 -C 4 alkyl, and branched C 3 -C 4 alkyl; or any two adjacent substituents R 2 -R 6 together form a ring of 5 or 6 members; and n is 1 or 0.

12. A method of imparting to, or modifying in, a flavour composition or comestible product, a kokumi sensation, comprising the addition to said flavour composition or comestible product of at least one compound of formula (I)

wherein one of X 1 , X 2 , or X 3 is selected from the group consisting of S, N and O and the remaining two are CH 2 ; and A is selected from

in which R 2 , R 3 , R 4 R 5 , R 6 are independently selected from the group consisting of H, methyl, ethyl, propyl, OH, OMe, OEt, COOH, COOR 7 , in which R 7 is selected from linear C 1 -C 7 alkyl, branched C 3 -C 7 alkyl, and CONR 8 R 9 , in which R 8 and R 9 are independently selected from hydrogen, straight C 3 -C 7 alkyl, and branched C 3 -C 4 alkyl; or any two adjacent substituents R 2 -R 6 together form a ring of 5 or 6 members; and n is 1 or 0.

13. The method according to claim 1 , in which the at least one compound of formula (I) is added in a concentration of from 0.01 ppm to 500 ppm by weight based on the weight of the comestible product.

14. The method according to claim 10 , in which the at least one compound of formula (I) is added in a concentration of from 0.01 ppm to 500 ppm by weight based on the weight of the comestible product, or at a concentration of 0.01% to 99.9% by weight of flavour components of the flavour composition.

15. The method according to claim 11 , in which the at least one compound of formula (I) is added in a concentration of from 0.01 ppm to 500 ppm by weight based on the weight of the comestible product, or at a concentration of 0.01% to 99.9% by weight of flavour components of the flavour composition.

16. The method according to claim 12 , in which the at least one compound of formula (I) is added in a concentration of from 0.01 ppm to 500 ppm by weight based on the weight of the comestible product, or at a concentration of 0.01% to 99.9% by weight of flavour components of the flavour composition.

Assignees

• Givaudan Sa
• Givaudan Sa

Inventors

• Bom David C

Classifications

• A23L27/2054 Primary

  having nitrogen as the only hetero atom · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title

• A23L27/2056

  having at least two different hetero atoms, at least one being a nitrogen atom · CPC title

• C07D213/32

  Sulfur atoms · CPC title

• C07D213/28

  Radicals substituted by singly-bound oxygen or sulphur atoms · CPC title