# US 10,119,096 B2 · Spearmint flavor enhancer

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- Number: US 10,119,096 B2
- Document ID: US10119096B2
- Status: Granted
- Kind: B2
- Application number: 14/821,241
- Filed: 2015-08-07
- Published: 2017-02-09
- Granted: 2018-11-06
- Earliest claimed: 2015-08-07
- Assignees: Symrise AG
- Applicants: Symrise Inc.
- Inventors: Gennadiy G. Kolomeyer; Douglas Ferone
- Web page: https://patentgrep.com/patent/US10119096B2

## CPC

- C11B 9/0034: {the ring containing six carbon atoms}
- A23L 2/56: Flavouring or bittering agents (sweeteners A23L2/60)
- A23L 27/12: from fruit, e.g. essential oils
- A23L 27/203: {Alicyclic compounds}
- A23L 27/88: {Taste or flavour enhancing agents}
- A61K 8/347: {Phenols}
- A61K 8/35: Ketones, e.g. benzophenone
- A61K 8/37: Esters of carboxylic acids
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS

## Abstract

Spearmint flavor enhancers and methods for the production thereof. The spearmint flavor enhancers may include l-carvone, l-carveol isomers, and d-dihydrocarveol isomers. The spearmint flavor enhancers may further include l-isocarveol isomers, l-carvyl acetate isomers, d-dihydrocarvyl acetate isomers, and l-isocarvyl acetate isomers.

## Claims

### Claim 1

A method for obtaining a spearmint flavor enhancer comprising the following steps:
(i) fractionating crude carveol to produce a first plurality of distillation fractions;
(ii) combining a selected group of one or more of the first plurality of distillation fractions rich in l-carvone, l-carveol, d-dihydrocarveol, and l-isocarveol to produce a mixture;
(iii) acetylating the mixture to produce an acetylation product;
(iv) fractionating the acetylation product to produce a second plurality of distillation fractions, and
(v) combining a selected group of one or more of the second plurality of distillation fractions to obtain said spearmint flavor enhancer,
wherein said spearmint flavor enhancer shows the following composition:
(a) about 30 to about 50 percent by weight of l-carvone, and
(b) about 50 to about 70 percent by weight of l-carvyl acetate isomers,
on condition that the amounts add, optionally with further constituents, to 100 percent by weight.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the crude carveol is obtained by a d-limonene oxide rearrangement reaction.

### Claim 3 (depends on 1)

The method according of claim 1, wherein the crude carveol comprises l-carvone, l-carveol isomers, and d-dihydrocarveol isomers.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the crude carveol further comprises one or more cyclic alcohols.

### Claim 5 (depends on 4)

The method according to claim 4, wherein the one or more cyclic alcohols are selected from the group consisting of isolimonene-l-ol isomers, l-methyl-3-isopropenyl-cyclopentyl methanol isomers, and isocarveol isomers.

### Claim 6 (depends on 1)

The method according to claim 1, wherein the selected group of one or more of the plurality of distillation fractions comprise l-isocarveol isomers.

### Claim 7 (depends on 1)

The method according to claim 1, wherein the spearmint flavor enhancer comprises less than 0.1% by weight of iso-Limonen-l-ol isomers.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the spearmint flavor enhance comprises less than 0.1% by weight of l-methyl-3-isopropenyl-cyclopentyl methanol isomers.

### Claim 9 (depends on 8)

The method according to claim 8, wherein fractionating the acetylation product comprises removing acetic acid formed in the acetylating step.

### Claim 10 (depends on 1)

The method of claim 1, wherein said spearmint flavor enhancer further comprises 0.1 to about 5 percent by weight of l-carveol isomers.

### Claim 11 (depends on 1)

The method of claim 1, wherein said spearmint flavor enhancer further comprises 0.1 to about 2 percent by weight of d-dihydrocarveol isomers.

### Claim 12 (depends on 1)

The method of claim 1, wherein said spearmint flavor enhancer further comprises 0.1 to about 1 percent by weight of l-isocarveol isomers.

### Claim 13 (depends on 1)

The method of claim 1, wherein said spearmint flavor enhancer further comprises 0.1 to about 2 percent by weight of d-dihydrocarvyl acetate isomers.

### Claim 14 (depends on 1)

The method of claim 1, wherein said spearmint flavor enhancer further comprises 0.1 to about 10 percent by weight of l-isocarvyl acetate isomers.

### Claim 15 (depends on 1)

The method of claim 1, wherein the l-carveol isomers, dihydrocarveol isomers and l-isocarveol isomers are converted to the corresponding acetates partially or completely.