Organic Compounds

Patent metadata

Field	Value
Publication number	US-2016278408-A1
Application number	US-201314916793-A
Country	US
Kind code	A1
Filing date	Oct 2, 2013
Priority date	Oct 2, 2013
Publication date	Sep 29, 2016
Grant date	—

Abstract

This disclosure relates to flavour modification and to compounds of formula (I)

wherein
X is —(CH 2 ) m — wherein m is an integer from 7 to 10, or X is C 7 -C 10 alkenyl, and
i) n is 1, R 1 and R 3 are hydrogen, and R 2 is the residue of a proteinogenic amino acid;
ii) n is 1, R 2 is hydrogen, and R 1 and R 3 together are —CH 2 —CH 2 —CH 2 —; or
iii) n is 2 or 3 and R 1 , R 2 and R 3 are hydrogen,

useful in modifying flavours.

First claim

1 . A flavour composition comprising a flavour co-ingredient, and a compound of formula (I) and/or an edible salt thereof

wherein
X is —(CH 2 ) m — wherein m is an integer from 7 to 10, or X is C 7 -C 10 alkenyl, and
i) n is 1, R 1 and R 3 are hydrogen, and R 2 is the residue of a proteinogenic amino acid; or,
ii) n is 1, R 2 is hydrogen, and R 1 and R 3 together are —CH 2 —CH 2 —CH 2 —; or,
iii) n is 2 or 3 and R 1 , R 2 and R 3 are hydrogen.

2 . A flavour composition according to claim 1 wherein the flavour co-ingredient is selected from: sugars, fats, salts, monosodium glutamate, calcium ions, phosphate ions, organic acids, proteins, purines, flavours, and mixtures thereof.

3 . A comestible product comprising a compound of formula (I) and/or an edible salt thereof

wherein
X is —(CH 2 ) m — wherein in is an integer from 7 to 10, or X is C 7 -C 10 alkenyl, and
i) n is 1, R 1 and R 3 are hydrogen, and R 2 is the residue of a proteinogenic amino acid; or
ii) n is 1, R 2 is hydrogen, and R 2 and R 3 together are —CH 2 —CH 2 —CH 2 —; or
iii) n is 2 or 3 and R 1 , R 2 and R 3 are hydrogen.

4 . A compound of formula (I) selected from:
9-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-9-oxononanoic acid; 1-(8-carboxyoctanoyl)pyrrolidine-2-carboxylic acid; and, 9-((3-carboxypropyl)amino)-9-oxononanoic acid.

5 . A method of modifying the taste of comestible composition comprising at least one flavour co-ingredient comprising the step of: adding to or including in said composition a compound of formula (I) and/or an edible salt thereof

wherein
X is —(CH 2 ) m — wherein m is an integer from 7 to 10, or X is C 7 -C 10 alkenyl, and
i) n is 1, R 1 and R 3 are hydrogen, and R 2 is the residue of a proteinogenic amino acid; or,
ii) n is 1, R 2 is hydrogen, and R 1 and R 3 together are —CH 2 —CH 2 —CH 2 —; or,
iii) n is 2 or 3 and R 2 and R 3 are hydrogen.

6 . A taste-modifying agent adapted for use in a consumable product, the taste-modifying agent comprising a compound of formula (I)

wherein
X is —(CH 2 ) m — wherein m is an integer from 7 to 10, or X is C 7 -C 10 alkenyl, and
i) n is 1, R 1 and R 3 are hydrogen, and R 2 is the residue of a proteinogenic amino acid; or
ii) n is 1, R 2 is hydrogen, and R 1 and R 3 together are —CH 2 —CH 2 —CH 2 —; or,
iii) n is 2 or 3 and R 1 , R 2 and R 3 are hydrogen.

7 . A flavour composition according to claim 1 , wherein the compound of Formula (I) is selected from:
9-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-9-oxononanoic acid; 1-(8-carboxyoctanoyl)pyrrolidine-2-carboxylic acid; and, 9-((3-carboxypropyl)amino)-9-oxononanoic acid.

8 . A comestible product according to claim 3 , wherein the compound of Formula (I) is selected from:
9-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-9-oxononanoic acid; 1-(8-carboxyoctanoyl)pyrrolidine-2-carboxylic acid; and, 9-((3-carboxypropyl)amino)-9-oxononanoic acid.

9 . A method according to claim 5 , wherein the compound of Formula (I) is selected from:
9-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-9-oxononanoic acid; 1-(8-carboxyoctanoyl)pyrrolidine-2-carboxylic acid; and, 9-((3-carboxypropyl)amino)-9-oxononanoic acid.

10 . A taste-modifying agent according to claim 6 , wherein the compound of Formula (I) is selected from:
9-((1-carboxy-2-(1H-indol-3-yl)ethyl)amino)-9-oxononanoic acid; 1-(8-carboxyoctanoyl)pyrrolidine-2-carboxylic acid; and, 9-((3-carboxypropyl)amino)-9-oxononanoic acid.

Assignees

• Givaudan Sa

Inventors

• Shi Feng
• Haiber Stephan
• Lam An Minh
• Van Ommeren Esther
• Wang Yili

Classifications

• A23L27/202

  Aliphatic compounds · CPC title

• C07D207/16

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07C233/47

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton · CPC title

• A23L27/2022

  containing sulfur · CPC title

• A23L27/88 Primary

  Taste or flavour enhancing agents · CPC title