HEMIACETYL PROFLAVORS

• US 20170339986A1
• Filed: 12/21/2015
• Published: 11/30/2017
• Est. Priority Date: 12/24/2014
• Status: Active Grant

• Current Assignee: Firmenich SA (DSM-Firmenich AG)
• Original Assignee: Firmenich SA (DSM-Firmenich AG)
• Inventors: WOMACK, Gary B., SILLICK, Matthew
• Granted Patent: US 10,638,779 B2
• Time in Patent Office: Days
• CPC Class Codes: A23L 2/56 Flavouring or bittering agents sweeteners A23L2/60
• CPC Class Codes: A23L 27/2028 Carboxy compounds
• CPC Class Codes: A23L 27/29 Fruit flavours
• CPC Class Codes: A23V 2002/00 Food compositions, function of food ingredients or processes for food or foodstuffs
• CPC Class Codes: C07C 69/38 Malonic acid esters
• CPC Class Codes: C07C 69/40 Succinic acid esters
• CPC Class Codes: C07C 69/44 Adipic acid esters
• CPC Class Codes: C07C 69/60 Maleic acid esters; Fumaric acid esters

Abstract

Provided herein is a compound having the formula I

wherein R1 and R2 are independently selected from a branched or straight C₁-C₆ alkyl and a C₁-C₆ 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 comprising delivering a compound of formula I to the aqueous solution wherein R1 and R2 are independently selected from a branched or straight C₁-C₆ alkyl and a C₁-C₆ 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 is a flavor or aroma-modifying composition comprising:

• i) a flavor or aroma-conferring or modifying ingredient, at least one compound according to formula (I) above;
• 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.

Claims

1. A compound having the formula I

2. The compound as recited in claim 1 wherein R¹ and R² are independently a straight or branched C₁-C₄ akyl.

3. The compound as recited in claim 2 wherein R¹ and R² are independently selected from the group consisting of methyl, ethyl, propyl, and butyl.

4. The compound as recited in any one of claims 1 to 3 wherein n is 1 and x is 2.

5. The compound as recited in any one of claims 1-3 wherein n is 2 and x is independently 0, 1 or 2.

6. The compound as recited in any one of claims 1 to 3 wherein n is 3, 4, 5 or 6 and x is independently 0, 1 or 2.

7. The compound as recited in claim 1 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.

14. A flavor-modifying composition comprising:

i) a flavor or aroma-conferring or modifying ingredient, at least one compound according to formula (I) as defined in any one of claims 1 to 8;

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.

15. A flavored article comprising:

i) at least one compound of formula (I), as defined in any one of claims 1 to 8, or a composition as defined in claim 9; and

ii) a foodstuff base.

8. A method of releasing acetaldehyde into an aqueous solution comprising delivering a compound of formula I:

9. The method as recited in claim 9 wherein R¹ and R² are independently a straight or branched C₁-C₄ akyl.

10. The method as recited in claim 10 wherein R¹ and R² are independently selected from the group consisting of methyl, ethyl, propyl, and butyl.

11. The method as recited in any one of claims 8-11 wherein n is 1 and x is 2.

12. The method as recited in any one of claims 8-11 wherein n is 2 and x is independently 0, 1 or 2.

13. The method as recited in 8 wherein Compound 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.