Organic compounds

Patent metadata

Field	Value
Publication number	US-10975018-B2
Application number	US-201414916830-A
Country	US
Kind code	B2
Filing date	Oct 1, 2014
Priority date	Oct 2, 2013
Publication date	Apr 13, 2021
Grant date	Apr 13, 2021

Abstract

A stock solution comprising a compound of formula (I)

Wherein
R 1 together with the carbonyl group to which it is attached is a residue of a carboxylic acid, and NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid, in particular a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

First claim

The invention claimed is:

1. A method of isolating and recovering a compound according to the formula (I) which exhibits taste modifying properties when incorporated within an edible composition or within a flavour composition,

wherein
R 1 together with the carbonyl group to which it is attached is a residue of a
carboxylic acid, and
NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid;
from a reaction mixture comprising the compound in a reaction solvent, the method comprising the steps of:
prior to removal of reaction solvent from the reaction mixture by evaporation, adding to the reaction mixture an extraction solvent for the compound, said extraction solvent having a higher boiling point than the reaction solvent, and
subsequent to the evaporation of and removal of the reaction solvent from the reaction mixture containing the compound of formula (I), the reaction solvent and the extraction solvent, the compound of formula (I) is recovered in the form of a stock solution containing the compound of formula (I) in the extraction solvent.

2. A method of forming a stock solution comprising the steps of:
isolating and recovering a compound which exhibits taste modifying properties when incorporated within an edible composition or within a flavour composition according to the formula (I)

wherein
R 1 together with the carbonyl group to which it is attached is a residue of a
carboxylic acid, and
NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid;
from a reaction mixture comprising the compound in a reaction solvent, the method comprising the steps of:
prior to removal of the reaction solvent from the reaction mixture by evaporation, adding to the reaction mixture an extraction solvent for the compound which has a higher boiling point than the boiling point of the reaction solvent, and,
subsequently, separating the compound according to formula (I) from the reaction solvent, and recovering from the reaction mixture a stock solution containing the compound and the extraction solvent.

3. A method according to claim 1 wherein the extraction solvent is selected from water-miscible alcohols and derivatives thereof.

4. A method according to claim 3 wherein the extraction solvent is selected from: ethanol, glycerol, propylene glycol, triacetine or miglyol, or mixtures thereof.

5. A method according to claim 3 , wherein the extraction solvent is propylene glycol.

6. A stock solution comprising up to 25% by weight of a compound of formula (I) which exhibits taste modifying properties when incorporated within an edible composition or within a flavour composition

wherein
R 1 together with the carbonyl group to which it is attached is a residue of a
carboxylic acid, and NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid;
in a solvent selected from water-miscible alcohols and/or derivatives thereof.

7. A stock solution according to claim 6 wherein the solvent is selected from: ethanol, glycerol, ethylene glycol, propylene glycol, triacetine or miglyol, or mixtures thereof.

8. A stock solution according to claim 6 , wherein the solvent is propylene glycol.

9. A stock solution according to claim 6 wherein the compound of formula (I) is present in an amount of up to 15% by weight.

10. A spray dried powder comprising a compound according to formula (I) which exhibits taste modifying properties when incorporated within an edible composition or within a flavour composition

wherein
R 1 together with the carbonyl group to which it is attached is a residue of a
carboxylic acid, and NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid.

11. A spray dried powder according to claim 10 , comprising a carrier material selected from a maltodextrin having a dextrose equivalent (DE) of 3 to 25, or gum Arabic.

12. A spray dried powder according to claim 10 wherein the compound of formula (I) is present in an amount of up to 1.5% by weight based on the total weight of the powder.

13. A spray dried powder according to claim 10 formed from a stock solution comprising up to 25% by weight of a compound of formula (I)

wherein
R 1 together with the carbonyl group to which it is attached is a residue of a
carboxylic acid, and NR 2 R 3 , in which R 3 is H or together with R 2 and the N-atom to which they are attached, a 5-membered ring, is a residue of an amino acid.

14. The method according to claim 1 , wherein:
the residue of an amino acid is selected from: a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

15. The method according to claim 2 , wherein:
the residue of an amino acid is selected from: a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

16. The stock solution according to claim 6 , wherein:
the residue of an amino acid is selected from: a proteinogenic amino acid, ornithine, gamma-aminobutyric acid or beta alanine, or a 1-amino cycloalkyl carboxylic acid.

17. The method according to claim 1 , wherein the stock solution contains 5% to 30% by weight of the compound of formula (I).

18. The method according to claim 2 , wherein the stock solution contains 5% to 30% by weight of the compound of formula (I).

19. The method according to claim 1 , wherein the compound of formula (I) is represented by the following structure:

and wherein:
n is 1, 2, 3 or 4.

20. The method according to claim 1 , wherein the compound of formula (I) is represented by the following structure:

and wherein:
m is 0 or 1.

21. The method according to claim 1 , wherein the compound of formula (I) is represented by the following structure:

and wherein:
R 3 is hydrogen is methyl, and
R 4 is methyl, ethyl or iso-propyl.

22. The method according to claim 1 , wherein the compound of formula (I) is represented by the following structure:

23. The method according to claim 1 , wherein the compound of formula (I)

Assignees

• Givaudan Sa

Inventors

• Staghouwer Harm
• Thoen Chris
• Van Buel Michel

Classifications

• A23L27/88

  Taste or flavour enhancing agents · CPC title

• A23L27/21 Primary

  containing amino acids · CPC title

• A23L27/202

  Aliphatic compounds · CPC title

• A23V2002/00

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

• C07C231/24 Primary

  Separation; Purification · CPC title