# US 9,434,676 B2 · Flavor and fragrance formulation (VI)

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- Number: US 9,434,676 B2
- Document ID: US9434676B2
- Status: Granted
- Kind: B2
- Application number: 14/432,252
- Filed: 2013-10-07
- Published: 2015-10-15
- Granted: 2016-09-06
- Earliest claimed: 2012-10-08
- Assignees: Dsm IP Assets B.V.
- Applicants: Dsm IP Assets B.V.
- Inventors: Raphael Beumer; Johannes Tschumi; Michael Gressly
- Web page: https://patentgrep.com/patent/US9434676B2

## CPC

- C07C 69/145: of unsaturated alcohols
- A23L 27/2026: {Hydroxy compounds}
- A23L 27/2028: {Carboxy compounds}
- A61K 8/342: {Alcohols having more than seven atoms in an unbroken chain}
- A61K 8/37: Esters of carboxylic acids
- A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00)
- C07C 33/025: with only one double bond
- C07C 67/00: Preparation of carboxylic acid esters
- C11B 9/0015: {containing oxygen as the only heteroatom}
- C11B 9/0019: {carbocylic acids; Salts or esters thereof}
- C11D 3/50: Perfumes
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- 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)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

The present invention relates to the use of specific organic compounds of formula (I) as flavor and fragrance material. Furthermore the invention relates to a new specific organic compound, as well as to flavor and fragrance formulations comprising at least one of the specific organic compounds.

## Claims

### Claim 1

A flavor and fragrance formulation comprising at least one compound of formula (I):
wherein R1 is —OH or —O(CO)CH3.

### Claim 2 (depends on 1)

The flavor and fragrance formulation according to claim 1 comprising 0.0001-10 wt-%, relative to the total weight of the flavor and fragrance formulation, of at least one compound of formula (I).

### Claim 3 (depends on 1)

The flavor and fragrance formulation according to claim 1, wherein the flavor and fragrance formulation is solid, gel-like or liquid.

### Claim 4 (depends on 1)

The flavor and fragrance formulation according to claim 1, wherein the flavor and fragrance formulation is a perfume, hair care product, household product, laundry product, body care product or cosmetic product.

### Claim 5

A method of improving, enhancing or modifying a flavor and fragrance formulation which comprises adding to the flavor or fragrance formulation an olfactory acceptable amount of at least one compound of formula (I):
wherein R1 is —OH or —O(CO)CH3.

### Claim 6

A compound of formula (Ib):
wherein AcO represents an acetyloxy group CH3(CO)O—.

### Claim 7

A process for the manufacture of a compound of formula (Ib):
wherein AcO represents an acetyloxy group CH3(CO)O—, the process comprising the steps of:
i) ethinylating 5,6-dimethyl-5-hepten-2-on to 3,6,7-trimethyl-6-octen-1-in-3-ol;
ii) acylating 3,6,7-trimethyl-6-octen-1-in-3-ol to 3,6,7-trimethyl-6-octen-1-in-3-yl acetate; and
iii) hydrogenating the C≡C triple bond of 3,6,7-trimethyl-6-octen-1-in-3-yl acetate to the saturated C—C bond in the presence of a Lindlar catalyst leading to the compound of formula (Ib).