Process for making flavor and fragrant compounds

Patent metadata

Field	Value
Publication number	US-2024191261-A1
Application number	US-202418587305-A
Country	US
Kind code	A1
Filing date	Feb 26, 2024
Priority date	Feb 3, 2015
Publication date	Jun 13, 2024
Grant date	—

Abstract

Described herein are methods of producing hexenols including: 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, where 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 composition comprising (Z)-3-hexenol produced by a method of producing an alcohol comprising:
a) contacting a 13-hydroperoxide of a polyunsaturated fatty acid selected from the group consisting of linoleic acid and alpha linolenic acid with a 13-hydroperoxide lyase to form a hexenal; and b) reducing the hexenal 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 the group consisting of NADH and NADPH; the hydroperoxide lyase is stable in the presence of the hydride donor, thus allowing for the concomitant hydroperoxide cleavage and hexanal reduction; and the method is performed in the absence of intact cells; wherein the composition comprises (Z)-3-hexenol in an amount of about greater than or equal to 12000 mg/L and is further provided with about less than or equal to about 170 to about 400 mg/L of the total amount of n-hexanal, (Z)-3-hexenal, (E)-2-hexenal, (E)-2-hexenol, and n-hexanol wherein the n-hexanal, (Z)-3-hexenal, (E)-2-hexenal, (E)-2-hexenol and n-hexanol have not been removed after processing.

2 . The composition as recited in claim 1 , wherein the ratio (Z)-3-hexenol to the total amount of n-hexanal, (Z)-3-hexenal, (E)-2-hexenal, (E)-2-hexenol, and n-hexanol ranges, by weight, from about 30:1 up to at least about 71:1.

3 . The composition as recited in claim 1 , comprising (Z)-3-hexenol wherein the composition comprises (Z)-3-hexenol in an amount of about greater than or equal to 12000 mg/L and is further provided with about less than or equal to 400 mg/L of the total amount of n-hexanal, (Z)-3-hexenal, (E)-2-hexenal, (E)-2-hexenol, and n-hexanol produced in the reaction wherein the n-hexanal, (Z)-3-hexenal, (E)-2-hexenal, (E)-2-hexenol, and n-hexanol have not been removed after processing.

4 . A composition comprising (Z,Z)-3,6-nonadienol produced by a method of producing an alcohol comprising:
a) contacting a 9-hydroperoxide of a polyunsaturated fatty acid selected from the group consisting of linoleic acid and alpha linolenic 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 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 the group consisting of 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; wherein the composition comprises (Z,Z)-3,6-nonadienol in an amount greater than or equal to about 0.74 g/l, and wherein the composition may comprise about less than or equal to about 1 g/l (Z)-3-nonenol.

5 . The composition as recited in claim 4 , wherein the ratio of (Z,Z)-3,6-nonadienol to (Z)-3-nonenol ranges from about 4.63 up to about 25:1.

6 . A product obtained from a method of producing an alcohol comprising:
a) contacting a 9- or 13-hydroperoxide of a polyunsaturated fatty acid selected from the group consisting of 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 the group consisting of 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.

7 . The composition of claim 6 , wherein the composition comprises no (Z)-3-nonenol.

8 . The composition of claim 6 , wherein the composition comprises (Z,Z)-3,6-nonadienol in an amount greater than or equal to about 4 g/l, and wherein the composition may comprise about less than or equal to about 0.16 g/l (Z)-3-nonenol.

Assignees

• Firmenich & Cie

Inventors

• Bruhlmann Fredi
• Buller Rebecca

Classifications

• C12P7/24

  containing a carbonyl group · CPC title

• C12N9/88

  Lyases (4.) · CPC title

• C12N9/004

  Cytochrome-b5 reductase (1.6.2.2) · CPC title

• C11B9/0015

  containing oxygen as the only heteroatom · CPC title

• C07B31/00

  Reduction in general · CPC title