N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds

Patent metadata

Field	Value
Publication number	US-10201175-B2
Application number	US-201314386084-A
Country	US
Kind code	B2
Filing date	Mar 28, 2013
Priority date	Mar 30, 2012
Publication date	Feb 12, 2019
Grant date	Feb 12, 2019

Abstract

Compounds represented by the formula

and their edible salts, and edible compositions containing same
wherein
R 1 is an alkyl residue containing 6 to 20 carbon atoms, or an alkene residue containing from 9 to 25 carbon atoms with 1 to 6 double bonds, such that R 1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and the amino acid residue connected to the carbonyl carbon atom is a residue of a 1-amino cycloalkane carboxylic acid (ACCA),
and n is 1, 2, 3 or 4.

First claim

The invention claimed is:

1. A flavor composition adapted for use in an edible composition comprising:
1 ppb to 10 ppm by weight based upon the weight of the edible composition of a compound selected from the group consisting of:
N-palmitoyl 1-amino-cyclopropyl carboxylic acid (C16:0-ACCA),
N-stearoyl 1-amino-cyclopropyl carboxylic acid (C18:0-ACCA),
N-linoleoyl 1-amino-cyclopropyl carboxylic acid (C18:2-ACCA),
N-linolenoyl 1-amino-cyclopropyl carboxylic acid (C18:2-ACCA),
N-oleoyl 1-amino-cyclopropyl carboxylic acid (C18:1-ACCA),
N-(9-palmitenoyi) 1-amino-cyclopropyl carboxylic acid (C16:1-ACCA),
N-decanoyl 1-amino-cyclopropyl carboxylic acid (C10:0-ACCA), and,
N-geranoyl 1-amino-cyclopropyl carboxylic acid (C10:2-ACCA),
wherein,

one or more of the foregoing compounds accentuates the existing flavour or existing mouth feel characteristics of an edible foodstuff product which further comprises at least one flavour co-ingredient, or of a beverage product which further comprises at least one flavour co-ingredient , when one or more of the foregoing compounds are incorporated therein.

2. A stock solution comprising 0.01 to 1% by weight of a compound selected from the group consisting of:
N-palmitoyl 1-amino-cyclopropyl carboxylic acid (C16:0-ACCA),
N-stearoyl 1-amino-cyclopropyl carboxylic acid (C18:0-ACCA),
N-linoleoyl 1-amino-cyclopropyl carboxylic acid (C18:2-ACCA),
N-linolenoyl 1-amino-cyclopropyl carboxylic acid (C18:2-ACCA),
N-oleoyl 1-amino-cyclopropyl carboxylic acid (C18:1-ACCA),
N-(9-palmitenoyl) 1-amino-cyclopropyl carboxylic acid (C16:1-ACCA),
N-decanoyl 1-amino-cyclopropyl carboxylic acid (C10:0-ACCA), and,
N-geranoyl 1-amino-cyclopropyl carboxylic acid (C10:2-ACCA),
wherein,

one or more of the foregoing compounds accentuates the existing flavour or existing mouth feel characteristics of an edible foodstuff product which further comprises at least one flavour co-ingredient, or of a beverage product which further comprises at least one flavour co-ingredient , when one or more of the foregoing compounds are incorporated therein at concentrations of 1 ppb to 10 ppm by weight based on the weight of the edible foodstuff product or beverage product.

3. A stock solution according to claim 2 which further comprises a solvent selected from the group consisting of: ethanol, triacetine, glycerol and miglyol and mixtures thereof.

4. A flavour composition according to claim 1 further comprising an ingredient selected from the group consisting of: sugars, fats, salt, MSG, calcium ions, phosphate ions, organic acids, proteins, purines and mixtures thereof.

5. A flavour composition according to claim 1 further comprising a carrier material and an adjuvant.

6. A flavour composition according to claim 5 wherein the adjuvant is an anti-oxidant.

7. A flavour composition according to claim 1 wherein the flavour composition is in the form of an emulsion.

8. A flavour composition according to claim 1 wherein the flavour composition is in the form of a powder.

9. A flavour composition according to claim 8 wherein the flavour composition is a spray dried powder.

10. A flavour composition adapted for use in an edible composition according to claim 1 , which flavor composition is in the form of a powdered soft drink or a dry mix composition.

11. A flavour composition adapted for use in an edible composition according to claim 1 in the form of a snack food wherein the flavor composition is incorporated in the snack food or is applied topically to the snack food as a powder.

12. A flavour composition according to claim 1 in an alcoholic beverage.

13. A flavour composition according to claim 1 in an orally administrable tablet, capsule, powder or multiparticulate.

14. A flavour composition according to claim 1 in a caloric or non-caloric beverage further containing at least one carbohydrate sweetener selected from: sucrose, high fructose corn syrup, fructose and glucose, or at least one high intensity, non-nutritive sweetener selected from: aspartame, acesulfame K, sucralose, cyclamate, sodium saccharin, neotame, rebaudioside A, and/or stevia-based sweeteners.

15. A flavour composition according to claim 1 in a soy-based edible composition.

16. A flavor composition according to claim 1 , wherein the compound provides an organoleptic, fat booting effect flavor when included in an edible foodstuff product or beverage product.

17. A flavor composition according to claim 1 , wherein the compound provides an organoleptic, alcohol boosting effect flavor when included in an edible foodstuff product or beverage product.

18. A flavor composition according to claim 1 , wherein the compound provides an organoleptic, coolant boosting effect flavor when included in an edible foodstuff product or beverage product.

19. A flavor composition according to claim 1 , wherein the compound provides an organoleptic, umami boosting effect flavor when included in an edible foodstuff product or beverage product.

20. A flavor composition according to claim 1 , wherein the compound imparts sweetness and mouthfeel reminiscent of sugar when present in a beverage product.

21. A flavor composition according to claim 1 , wherein the compound imparts stability in a clouded beverage composition.

22. A flavor composition according to claim 1 in the form of an emulsion.

Assignees

• Givaudan Sa

Inventors

• Shi Feng
• Renes Harry
• Van Ommeren Esther
• Vorster Susanna Magdalena
• Wang Yili
• De Klerk Adri
• Haiber Stephan
• Houben Eric
• Elings Jacob

Classifications

• C12G2200/21

  Wine additives, e.g. flavouring or colouring agents · CPC title

• C12G3/06

  with flavouring ingredients · CPC title

• C07C2601/02

  with a three-membered ring · CPC title

• C07C233/49

  having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton · 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