GB2129419A

GB2129419A - 1,1-bis mercapto and alkylthio alka-2,4-dienes as flavoring compounds

Info

Publication number: GB2129419A
Application number: GB08231987A
Authority: GB
Inventors: Paul Robert Zanno; Thomas Holden Parliment; Robert Joseph Soukup; Richard Paul Mcnaught
Original assignee: General Foods Corp
Current assignee: General Foods Corp
Priority date: 1982-11-09
Filing date: 1982-11-09
Publication date: 1984-05-16
Also published as: SE8206231D0; GB2129419B; SE450193B; SE8206231L

Abstract

A flavoring composition comprising an effective amount of a compound of the following structure: <IMAGE> R1 is alkyl of 1 to 7 carbon atoms; and R2 and R3 are hydrogen or an alkyl group of 1 to 3 carbon atoms. These compounds impart a fatty, meaty, chicken-like and pork-like quality, flavor and aroma to food products.

Description

SPECIFICATION 1,1-bis (thioalkyl) alkyl-2,4-diene acetal as a flavoring compound BACKGROUND OF THE INVENTION This invention relates to a composition which imparts or enhances the flavor of foodstuffs. More particularly a flavoring composition has been discovered which imparts or enhancesthe meaty, chickenlike, fatty and port-like flavor, aroma and character of foodstuffs. A process is also disclosed for preparing the flavoring composition.

TECHNICAL FIELD Food products enhanced with poultry-like or pork-like flavors are known in the art and have long been used. There is considerable demand for these flavors in which the actual pork or poultry meat is not needed or is actually undesirable. For example, in the preparation of some sauces and purees a poultry or pork flavor is desired, but it is necessary to cook the food with the desired meat and then remove the meat by straining it, or some similar operation to obtain the final product ready for use.

While this method for preparing a flavored sauce of puree is effective it is time consuming and expensive.

Additionally, where weight, space and/or storage capability are a problem, e.g. when a convenience food is prepared; the presence of the actual meat may be undesirable because it will deteriorate in storage and spoil the food. Moreover, there are occasions when sterilizing or otherwise preserving the natural product is extremely deleterious to the flavor of the natural material and the desired natural flavor is lost.

Thus, it is a feature of this invention to provide a flavoring composition which can be incorporated in a wide range of foodstuffs.

It is a further feature of this invention to provide a process for preparing the flavoring composition.

DISCLOSURE OF THE INVENTION Briefly, this invention involves adding as a flavoring composition an effective amount of a flavoring compound having the following structure

wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are chosen from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms. The bis (thioalkyl) acetal is prepared by reacting aliphatic polyene aldehydes with alkyl thiols or hydrogen sulfide with the reaction rate being increased by use of appropriate organic solvents and catalysts.

This invention is directed to a flavoring composition which enhances or imparts unique flavor characteristics in foods. The flavoring composition comprises use of an effective amount of the compound 1 ,1-bis (thioalkyl) alkyl-2,4-diene acetal and has the following structure:

wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are chosen from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms. Preferably, R1 is a butyl or pentyl group and R2 and R3 are a hydrogen or methyl group. R2 and R3 can be different groups although preferably they are identical. When the compounds have alkyl groups with higher chain lengths than 7 carbon atoms for Rr, or higher than 3 carbon atoms for R2 and R3, the resultant compounds do not have the desired flavor, aroma and character.Within the above structure the flavoring composition of this invention includes, but is not limited to, the following flavoring compounds: 1 ,1-bis (thiomethyl) nona-2,4-diene acetal; 1,1-bis (thiomethyl) deca-2,4-diene acetal; 1,1-bis (thioethyl) nona-2,4-diene acetal; 1,1-bis (thiopropyl) deca-2,4-diene acetal; 1,1-bis (mercapto) hepta-2,4-diene acetal: 1-mercapto-1thiomethyl undeca-2,4-diene acetal; and 1 -thiomethyl-1 -thioethyl-octa-2,4-diene acetal.

The flavoring composition of this invention imparts a fatty, meaty, chicken-like, pork-like quality, flavor, aroma and character, with some of the compounds imparting a green, vegetable-like character when added in effective amounts to a food product. The type of flavor may vary slightly depending upon the amount of the flavoring composition employed, with higher amounts generally imparting a more pork, fatty flavor and the lower amounts imparting a meaty, chickeny flavor. The flavoring composition can be effectively incorporated in any one of a number of foodstuffs such as sauces, gravies, seasonings, stuffing mixes, soups, meats (including meat analogs and pet foods), or beverages.The level at which the flavoring compound is effective in foodstuffs in generally within the range of 0.1 to 100 parts per million, preferably 1 to 25 parts per million of the foodstuff.

To prepare the flavoring composition aliphatic polyene aldehydes react with alkyl thiols or hydrogen sulfide when mixed together to form 1,1 bis (thioalkyl) alkyl-2,4-diene acetals. The rate of reaction of these compounds can be increased by using an appropriate organic solvent (CHCl3, CH2Cl2, ethyl ether) and BF3, Lewis acids (AICI3, etc.) or mineral acids (HCI, etc.) as a catalyst.

The flavoring composition containing the bis (thioalkyl) acetal of this invention can be combined with other natural or synthetic flavors to provide a balanced flavor depending upon the desired end use.

The flavoring composition can also be fixed on or in a carrier to provide a dry flowable form by common methods, such as by spray or freeze drying the flavoring composition with a carrier such as dextrin, gum arabic, etc.

BEST MODE FOR CARRYING OUT THE INVENTION To a cooled (OoC.) solution of 25 ml. nona-2,4-dienal in 100 ml. of CHCI3 was added 25 ml of methyl mercaptan. To this solution (at OOC.) was then added 0.5 ml. of BF3: etherate. The mixture was allowed to come to room temperature, then stirred for 1 hour. After this time the mixture was distilled under vacuum giving 1 5 gm of 1,1 bis (thiomethyl) nona-2,4 diene acetal.

EXAMPLE 2 To a cooled (0 C.) solution of 25 ml. of deca-2,4-dienal in 100 ml. of CHIC13 was added 25 ml. of methyl mercaptan. To this solution (at 0 F) was then added 0.5 ml of BF3: etherate. The mixture was allowed to come to RT then stirred for 1 hour. After this time the mixture was distilled under vacuum giving 12.5 gm of 1,1 bis (thiomethyl) deca-2,4-diene acetal.

EXAMPLE 3 The flavoring composition 1 ,1-bis (thiomethyl) deca-2,4-diene acetal was incorporated into the following foodstuffs and at the following levels with the resultant flavor and aroma: Level of flavoring Observed Foodstuff Composition Flavor Oriental 6.6 ppm meaty, pork-like soup flavor Noodles (hydrated dry mix) 9.9 ppm more pork-like flavor, chicken-like, slightly fatty Beef Rice Mix 20 ppm more savory, fatty, meaty flavor (hydrated dry mix) Meatless Chow Mein (canned) 10 ppm more savory, meaty flavor EXAMPLE 4 The compound 1 1-bis (thiomethyl) alkyl-2,4-diene acetal with the following structure: SCH3 R1-CH=CH-CH=CH-C H SCH3 was evaluated for organoleptic properties varying the R1 substituent with the following results: : R1 Organoleptic Evaluation CH3 Green/Fatty/Oily/Fried CH3CH2 Green/Vegetable-like CH3(CH2)3 Chicken-like/Pork-like/Brothy/Fatty CH3(CH2)4 Chicken-like/Pork-like/Brothy/Fatty CH3(CH2)s Weak Fatty/Oily EXAMPLE 5 The compound 1,1 -bis (mercapto) alkyl-2,4-diene acetal with the following structure:

was evaluated for organoleptic properties varying the R1 substituent with the following results: R1 Organoleptic Evaluation CH3 Green/Fatty/Savory CH3 CH2 Sweet/Green/Fatty/Fried CH3(CH2)2 Green/Musty/Brothy CH3(CH2)s Cooked Oil/Fatty Browned

Claims

1. A flavoring composition comprising an effective amount of compound having the following structure:

wherein R1 is an alkyl group of 1 to 7 carbon atom% and R2 and R3 are chosen from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms.

2. Composition of Claim 1 wherein R1 is chosen from the group consisting of a butyl group and a pentyl group.

3. Composition of Claims 1 or 2 wherein R2 and R3 are chosen from the group consisting of hydrogen and a methyl group.

4. Composition of Claims 1 or 2 wherein R2 is the same as R3.

5. Composition of Claim 1 wherein the amount of the flavoring composition is within the range of 0.1 to 100 ppm of a foodstuff.

6. Composition of Claim 3 wherein the amount of the flavoring composition is within the range of 1 to 25 ppm of a foodstuff.

7. Composition of Claim 3 wherein the flavoring composition is incorporated into a foodstuff chosen from the group consisting of soup, sauce, stuffing mix, seasoning, meat and beverage.

8. Composition of Claim 1 further comprising a natural or synthetic flavor.

9. Composition of Claim 1 wherein the compound is fixed on a carrier.

10. Composition of Claim 1 wherein the compound is chosen from the group consisting of 1,1bis (thiomethyl) nona-2,4-diene acetal and 1,1bis (thiomethyl) deca-2,4-diene acetal.

11. A foodstuff comprising an effective amount of a flavoring compound having the following structure:

wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are chosen from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms.

12. Foodstuff of Claim 11 wherein R1 is chosen from the group consisting of a butyl group and a pentyl group.

1 3. Foodstuff of Claims 11 or 1 2 wherein R2 and R3 are chosen from the group consisting of hydrogen and a methyl group.

14. Foodstuff of Claims 11 or 12 wherein R2 is the same as R3.

1 5. Foodstuff of Claim 11 wherein the amount of the flavoring composition is within the range of 0.1 to 100 ppm of the foodstuff.

1 6. Foodstuff of Claim 1 3 wherein the amount of the flavoring composition is within the range of 1 to 25 ppm of the foodstuff.

17. Foodstuff of Claim 11 wherein the foodstuff is chosen from the group consisting of soup, sauce, seasoning, meat, stuffing mix, and beverage.

18. Foodstuff of Claim 11 further comprising other natural or synthetic flavors.

19. Foodstuff of Claim 11 wherein the flavoring compound is fixed on a carrier.

20. Foodstuff of Claim 11 wherein the flavoring compound is chosen from the group consisting of 1,1-bis (thiomethyl) nona-2,4-diene acetal and 1 1-bis (thiomethyl) deca-2,4-diene acetal.

21. A flavoring composition or a flavored foodstuff substantially as hereinbefore described.