Amber odorant

Patent metadata

Field	Value
Publication number	US-12139469-B2
Application number	US-202017420545-A
Country	US
Kind code	B2
Filing date	May 25, 2020
Priority date	May 27, 2019
Publication date	Nov 12, 2024
Grant date	Nov 12, 2024

Abstract

Described herein is a compound of formula (I)

in the form of any one of its stereoisomers or as a mixture thereof, and wherein R 1 represents a hydrogen atom, a C 1-3 alkyl group or C 2-3 alkenyl group; X represents an oxygen atom when R 2 represents a C 1-4 alkyl group or C 2-4 alkenyl group or X represents a CH2-O group when R 2 represents a C 2-4 alkenyl group or a MeC═O group. The use as a perfuming ingredient of this compound and this compound as part of a perfuming composition or of a perfuming consumer product are also described.

First claim

The invention claimed is:

1. A compound of formula

in the form of any one of its stereoisomers or as a mixture thereof, and wherein R 1 represents a hydrogen atom, a C 1-3 alkyl group or C 2-3 alkenyl group; X represents an oxygen atom when R 2 represents a C 1-4 alkyl group or C 2-4 alkenyl group or X represents a CH 2 —O group when R 2 represents a C 2-4 alkenyl group or a MeC═O group.

2. The compound according to claim 1 , characterized in that X represents an oxygen atom.

3. The compound according to claim 1 , characterized in that R 1 represents a hydrogen atom or a methyl group.

4. The compound according to claim 1 , characterized in that R 2 represents a methyl or an ethyl group.

5. The compound according to claim 1 , characterized in that the compound of formula (I) is in the form of a mixture of isomers comprising at least 55% of isomers with a R configuration on carbon 5 and at most 45% of isomers with a S configuration on carbon 5.

6. The compound according to claim 1 , characterized in that the compound of formula (I) is (1R,3S,5R,7R,8R, 10S, 13R)-5-methoxy-7,9,9,13-tetramethyl-4,6-dioxatetracyclo [6.5.1.0 1,10 .0 3,7 ] tetradecane, (1R,3S,5S,7R,8R, 10S, 13R)-5-methoxy-7,9,9,13-tetramethyl-4,6-dioxatetracyclo [6.5.1.0 1,10 .0 3,7 ] tetradecane, or a mixture thereof, (1R,3S,7R,8R, 10S,13R)-5-methoxy-5,7,9,9,13-pentamethyl-4,6-dioxatetracyclo [6.5.1.0 1,10 .0 3,7 ] tetradecane and (1R,3S,7R,8R,10S,13R)-5-ethoxy-5,7,9,9,13-pentamethyl-4,6-dioxatetracyclo [6.5.1.0 1,10 .0 3,7 ] tetradecane.

7. A method of using a compound of formula (I) as defined in claim 1 , the method comprising using the compound of formula (I) as a perfuming ingredient.

8. A method to confer, enhance, improve, or modify the odor properties of a perfuming composition or of a perfumed article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I) as defined in claim 1 .

9. A perfuming composition comprising:
i) at least one compound of formula (I), as defined in claim 1 ;
ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and
iii) optionally at least one perfumery adjuvant.

10. A perfumed consumer product comprising at least one compound of formula (I), as defined in claim 1 .

11. The perfumed consumer product according to claim 10 , characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

12. The perfumed consumer product according to claim 11 , characterized in that the perfumery consumer product is a fine perfume, a splash or eau de parfum, a cologne, a shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, a hair remover, a tanning or sun product, a nail product, a skin cleansing, a makeup, a perfumed soap, a shower or bath mousse, an oil or a gel, or a foot/hand care product, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, a furnisher care, a wipe, a dish detergent or a hard-surface detergent, a leather care product, a car care product.

13. A composition of matter comprising
a) 0.1 to 50% w/w of (1R,3S,7R,8R, 10S, 13R)-5,7,9,9,13-pentamethyl-5-[(1E)-1-propen-1-yl]-4,6-dioxatetracyclo [6.5.1.0 1,10 .0 3,7 ] tetradecane;
b) 10 to 99.9% w/w of compound of formula (I) as defined in claim 1 ; and
c) 20 to 80% w/w of (3R,3aR,6R,7S,8aS)-3,6,8,8-tetramethylhexahydro-1H-3a,7-methanoazulen-5 (4H)-one;
the percentage being relative to the total weight of the composition of matter.

14. A perfumed consumer product comprising a perfuming composition as defined in claim 9 .

15. The perfumed consumer product according to claim 14 , characterized in that the perfumery consumer product is a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product.

Assignees

• Firmenich & Cie

Inventors

• Lem George
• Reiter Maud
• Boschung Alain

Classifications

• C07D317/70 Primary

  condensed with ring systems containing two or more relevant rings · CPC title

• C07D317/64 Primary

  Oxygen atoms · CPC title