Process for making flavor and fragrant compounds

Patent metadata

Field	Value
Publication number	US-10941419-B2
Application number	US-201615547563-A
Country	US
Kind code	B2
Filing date	Feb 3, 2016
Priority date	Feb 3, 2015
Publication date	Mar 9, 2021
Grant date	Mar 9, 2021

Abstract

The present invention relates to the production of aromatic hexanols and compositions containing them. In particular provided herein are methods of producing hexenols comprising: a) contacting a hydroperoxide of a polyunsaturated fatty acid with a modified hydroperoxide lyase to form a hexenal; and b) reducing the hexenal to a hexenol in the presence of a hydride donor, a ketoreductase, and a co-factor wherein the contacting and reducing steps are carried out at essentially the same time in the substantial absence of baker's yeast.

First claim

What is claimed is:

1. A method of producing an alcohol comprising: a) contacting a 9- or 13-hydroperoxide of a polyunsaturated fatty acid selected from linoleic acid and alpha linolenic acid with the respective hydroperoxide lyase to form an aldehyde; and b) reducing the aldehyde to form the alcohol in the presence of a hydride donor, a ketoreductase, and a co-factor wherein the contacting and reducing steps are carried out concomitantly: wherein
the hydride donor is selected from the group consisting of a secondary alcohol, a primary alcohol, an alkandiol and a hydroxy acid or one of its esters;
the cofactor is selected from NADH and NADPH;
the hydroperoxide lyase is stable in the presence of the hydride donor, thus allowing for the concomitant hydroperoxide cleavage and aldehyde reduction; and
the method is performed in the absence of intact cells.

2. The method as recited in claim 1 comprising a) contacting a 13-hydroperoxide of the polyunsaturated fatty acid with a 13-hydroperoxide lyase to form a hexenal; and b) reducing the hexenal in the presence of the hydride donor, the ketoreductase, and the co-factor.

3. The method as recited in claim 1 comprising a) contacting a 13-hydroperoxide of a polyunsaturated fatty acid with a 13-hydroperoxide lyase to form n-hexanal; and b) reducing the hexanal in the presence of the hydride donor, the ketoreductase, and the co-factor.

4. The method as recited in claim 2 wherein the hexenal is (Z)-3-hexenal, the method further comprising reducing the (Z)-3-hexenal to (Z)-3-hexenol in the presence of a secondary alcohol, the ketoreductase, and the co-factor.

5. The method as recited in claim 1 comprising a) contacting a 9-hydroperoxide of the polyunsaturated fatty acid with a 9-hydroperoxide lyase to form an aldehyde selected from the group consisting of a nonenal and nonadienal; and b) reducing the aldehyde in the presence of the hydride donor, the ketoreductase, and the co-factor.

6. The method as recited in claim 1 wherein the aldehyde is selected from the group consisting of (Z)-3-nonenal and (Z,Z)-3,6-nonadienal, the method further comprising reducing the aldehyde in the presence of the hydride donor, the ketoreductase, and the cofactor.

7. The method as recited in claim 1 wherein the contacting and reducing steps are carried out in the absence of baker's yeast.

8. The method as recited claim 1 , wherein: the secondary alcohol is selected from the group consisting of isopropanol, isoamyl alcohol, glycerol, isobutanol, butan-2-ol, propylene glycol, fenchol, borneol, menthol, carveol, methyl-p-tolyl-carbinol, 8-cymenol, oct-1-en-3-ol, pentan-2-ol, pentan-3-ol, 4-methyl-2-pentanol, hexan-2-ol, heptan-2-ol, octan-2-ol, nonan-2-ol, decan-2-ol, and undecan-2-ol; the alkandiol is selected from the group consisting of butan-1,4-diol, butan-2,3-diol and ethylene glycol; and the hydroxy acid ester is selected from the group consisting of calcium lactate, ethyl lactate, propyl lactate and butyl lactate.

Assignees

• Firmenich & Cie

Inventors

• Bruhlmann Fredi
• Buller Rebecca

Classifications

• C12N9/004

  Cytochrome-b5 reductase (1.6.2.2) · CPC title

• C12N9/88

  Lyases (4.) · CPC title

• C11B9/0015

  containing oxygen as the only heteroatom · CPC title

• C12P7/04 Primary

  acyclic · CPC title

• C07B31/00

  Reduction in general · CPC title