Hemiacetyl proflavors

Patent metadata

Field	Value
Publication number	US-10638779-B2
Application number	US-201515538506-A
Country	US
Kind code	B2
Filing date	Dec 21, 2015
Priority date	Dec 24, 2014
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

Provided herein is a compound having the formula I

wherein R 1 and R 2 are independently selected from a branched or straight C 1-6 alkyl and a C 1-6 alkenyl, n is 1, 2, 3, 4, 5, or 6 and x is independently 0, 1, or 2; provided that when n is 1, x is 2. Also provided herein is a method of releasing acetaldehyde into an aqueous solution including delivering a compound of formula I to the aqueous solution, Also provided is a flavor or aroma-modifying composition including i) a flavor or aroma-conferring or modifying ingredient, at least one compound according to formula (I); ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and iii) optionally at least one flavor adjuvant.

First claim

The invention claimed is:

1. A method of releasing an acetaldehyde into an aqueous solution, the method comprising delivering an acetaldehyde precursor compound of formula (I):

to the aqueous solution wherein R 1 and R 2 are independently selected from a branched or straight C 1 -C 6 alkyl and a C 1 -C 6 alkenyl, n is 1, 2, 3, 4, 5 or 6, and x is independently 0, 1 or 2, provided that when n is 1, x is 2,
wherein the acetaldehyde is a flavor ingredient, a flavor-modifying ingredient, an aroma-conferring ingredient, or an aroma-modifying ingredient, and
wherein the acetaldehyde is released by hydrolysis of the acetaldehyde precursor compound of formula (I).

2. The method as recited in claim 1 wherein R 1 and R 2 are independently a straight or branched C 1 -C 4 alkyl.

3. The method as recited in claim 2 wherein R 1 and R 2 are independently selected from the group consisting of methyl, ethyl, propyl, and butyl.

4. The method as recited in claim 1 wherein n is 1 and x is 2.

5. The method as recited in claim 1 wherein n is 2 and x is independently 0, 1 or 2.

6. The method as recited in 1 wherein the compound of formula I is selected from the group consisting of bis(1-ethoxyethyl) succinate; bis(1-ethoxyethyl) adipate; bis(1-ethoxyethyl) fumarate; bis(1-propoxyethyl) succinate; bis(1-propoxyethyl) adipate; bis(1-propoxyethyl) fumarate; bis(1-butoxyethyl) succinate; bis(1-butoxyethyl) adipate, and bis(1-butoxyethyl) fumarate.

7. A flavor-modifying composition comprising:
i) at least one acetaldehyde precursor compound according to formula (I)

wherein R 1 and R 2 are independently selected from a branched or straight C 1 -C 6 alkyl and a C 1 -C 6 alkenyl, n is 1, 2, 3, 4, 5 or 6, and x is independently 0, 1 or 2, provided that when n is 1, x is 2,
wherein the acetaldehyde precursor compound of formula (I) is capable of hydrolysis in an aqueous solution to release an acetaldehyde into the aqueous solution, and
wherein the acetaldehyde is a flavor ingredient, a flavor-modifying ingredient, an aroma-conferring ingredient, or an aroma-modifying ingredient;
ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and
iii) optionally at least one flavor adjuvant.

8. A flavored article comprising:
i) at least one acetaldehyde precursor compound of formula (I)

wherein R 1 and R 2 are independently selected from a branched or straight C 1 -C 6 alkyl and a C 1 -C 6 alkenyl, n is 1, 2, 3, 4, 5 or 6, and x is independently 0, 1 or 2, provided that when n is 1, x is 2,
wherein the acetaldehyde precursor compound of formula (I) is capable of hydrolysis in an aqueous solution to release an acetaldehyde into the aqueous solution, and
wherein the acetaldehyde is a flavor ingredient, a flavor-modifying ingredient, an aroma-conferring ingredient, or an aroma-modifying ingredient; and
ii) a foodstuff base.

9. A flavored article comprising:
i) the flavor-modifying composition of claim 7 ; and
ii) a foodstuff base.

Assignees

• Firmenich & Cie

Inventors

• Womack Gary B
• Sillick Matthew

Classifications

• C07C69/44

  Adipic acid esters · CPC title

• C07C69/40

  Succinic acid esters · CPC title

• A23L2/56 Primary

  Flavouring or bittering agents (sweeteners A23L2/60) · CPC title

• C07C69/38 Primary

  Malonic acid esters · CPC title

• A23L27/2028

  Carboxy compounds · CPC title