# US 4,395,425 A · Use of Prins reaction products of diisoamylene derivatives to augment or enhance the aroma or taste of foodstuffs

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- Number: US 4,395,425 A
- Document ID: US4395425A
- Status: Granted
- Kind: A
- Application number: 06/391,588
- Filed: 1982-06-24
- Granted: 1983-07-26
- Earliest claimed: 1981-05-28
- Assignees: International Flavors & Fragrances Inc.
- Inventors: Richard M. Boden
- Web page: https://patentgrep.com/patent/US4395425A

## CPC

- A23G 4/06: characterised by the composition {containing organic or inorganic compounds}
- A24B 15/32: by acyclic compounds
- A24B 15/40: having only oxygen or sulfur as hetero atoms
- C07C 29/095: {of esters of organic acids}
- C07C 29/103: {of cyclic ethers}
- C07C 67/00: Preparation of carboxylic acid esters
- C07C 69/145: of unsaturated alcohols
- C07C 69/24: esterified with monohydroxylic compounds
- C07D 309/04: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C11B 9/0015: {containing oxygen as the only heteroatom}
- C11B 9/008: {the hetero rings containing six atoms}
- A23G: COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A24B: MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)

## Abstract

Described for use in augmenting or enhancing the aroma or taste of foodstuffs is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds; wherein the wavy line represents a carbon-carbon single bond or no bond; wherein when the wavy line represents a carbon-carbon single bond, Z represents methylene and when the wavy line represents no bond, Z represents hydrogen or C.sub.2 -C.sub.4 acyl prepared according to a Prins reaction between diisoamylene defined according to the structure: ##STR2## wherein one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds or one of the structures: ##STR3## formaldehyde of a formaldehyde source such as trioxane or paraformaldehyde in the presence of an acyl anhydride and an acid catalyst.

## Claims

### Claim 1

A process for augmenting or enhancing the aroma or taste of a foodstuff or chewing gum comprising the step of adding to said footstuff or chewing gum from about 0.2 parts per million up to about 150 parts per million based on total foodstuff composition or chewing gum composition of a mixture of compounds defined according to the structure: ##STR79## wherein R represents hydrogen or C.sub.2 -C.sub.4 acyl and wherein in each of the compounds of the mixture, one of the dashed lines is a carbon-carbon double bond and each of the other of the dashed lines are carbon-carbon single bonds.

### Claim 2 (depends on 1)

The process of claim 1 wherein R is n-propionyl.

### Claim 3 (depends on 1)

The process of claim 1 wherein R is isobutyryl.

### Claim 4 (depends on 1)

The process of claim 1 wherein R is acetyl.

### Claim 5 (depends on 1)

The process of claim 1 wherein R is hydrogen.

### Claim 6

A process for augmenting or enhancing the aroma or taste of a foodstuff or chewing gum composition comprising the step of adding to said foodstuff or chewing gum composition from about 0.2 parts per million up to about 150 parts per million based on total food composition or a chewing gum composition of a mixture of compounds defined according to the structure: ##STR80## wherein in the mixture in each of the molecules one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represent carbon-carbon single bonds.

### Claim 7

A process for augmenting or enhancing the aroma or taste of a foodstuff or chewing gum composition comprising the step of adding to said foodstuff or chewing gum composition from about 0.2 parts per million up to about 150 parts per million based on total food composition or chewing gum composition of the compound defined according to the structure: ##STR81##

### Claim 8

A process for augmenting or enhancing the aroma or taste of a foodstuff or chewing gum comprising the step of adding to said foodstuff or chewing gum from about 0.2 parts per million up to about 150 parts per million based on the total food composition or chewing gum composition of a mixture of compounds defined according to the structure: ##STR82## wherein in the mixture in each of the molecules of the mixture, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond.