Cyclododecadienone derivatives as perfuming ingredients

Patent metadata

Field	Value
Publication number	US-9637707-B2
Application number	US-201514939585-A
Country	US
Kind code	B2
Filing date	Nov 12, 2015
Priority date	Jun 22, 2011
Publication date	May 2, 2017
Grant date	May 2, 2017

Abstract

The present invention relates to compounds of formula

wherein one R group is a hydrogen atom and the other is a hydrogen atom or a C 1-3 alkyl group; and
each carbon-carbon double bond of said compound, independently from each other, can be in a configuration Z or E or a mixture thereof;

which are useful perfuming ingredients.

First claim

What is claimed is:

1. A compound of formula (I)

wherein one R group is a hydrogen atom and the other is a hydrogen atom or a C 1-3 alkyl group, wherein the compound (I) is in the form of a mixture of stereoisomers (4E,8E), (4Z,8E) and (4E,8Z), wherein the w/w ratio of (4E,8E)/[(4Z,8E)+(4E,8Z)] is between 20/80 and 1/99, or between 80/20 and 99.5/0.5.

2. The compound of claim 1 , wherein one R group is a hydrogen atom and the other is a hydrogen atom or a methyl or ethyl group.

3. The compound of claim 1 , wherein said compound (I) is (E,E)-4,8-cyclododecadien-1-one, (Z,E)-4,8-cyclododecadien-1-one, (E,Z)-4,8-cyclododecadien-1-one, (4E,8E)-12-methylcyclododeca-4,8-dienone, (4E,8Z)-12-methylcyclododeca-4,8-dienone, (4Z,8E)-12-methylcyclododeca-4,8-dienone, 2-methylcyclododeca-4,8-dienone or a mixture thereof.

4. A method of use of a compound of formula (I) wherein the method comprises imparting a hedonic effect through application of a compound of formula (I) as a perfuming ingredient

wherein one R group is a hydrogen atom and the other is a hydrogen atom or a C 1-3 alkyl group; and each carbon-carbon double bond of the compound (I), independently of each other, can be in a configuration Z or E or a mixture thereof.

5. The method of use of claim 4 , wherein one R group is a hydrogen atom and the other is a hydrogen atom or a methyl or ethyl group.

6. The method of use of claim 4 , wherein the compound (I) is in the form of a mixture of stereoisomers (4E,8E), (4Z,8E) and (4E,8Z), wherein the w/w ratio of (4E,8E)/[(4Z,8E)+(4E,8Z)] is between 20/80 and 1/99, or between 80/20 and 99.5/0.5.

7. The method of use of claim 4 , wherein the compound (I) is (E,E)-4,8-cyclododecadien-1-one, (Z,E)-4,8-cyclododecadien-1-one, (E,Z)-4,8-cyclododecadien-1-one, (4E,8E)-12-methylcyclododeca-4,8-dienone, (4E,8Z)-12-methylcyclododeca-4,8-dienone, (4Z,8E)-12-methylcyclododeca-4,8-dienone, 2-methylcyclododeca-4,8-dienone or a mixture thereof.

8. A perfuming composition comprising:
i) at least one compound of formula (I), as defined in claim 4 ;
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.

9. A perfuming composition according to claim 8 , wherein the perfumery base comprises at least one perfuming co-ingredient having a woody and/or musk character.

10. The perfuming composition of claim 8 , wherein one R group is a hydrogen atom and the other is a hydrogen atom or a methyl or ethyl group.

11. The perfuming composition of claim 8 , wherein said compound (I) is in the form of a mixture of stereoisomers (4E,8E), (4Z,8E) and (4E,8Z), wherein the w/w ratio (4E,8E)/[(4Z,8E)+(4E,8Z)] is comprised between 20/80 and 1/99, or between 80/20 and 99.5/0.5.

12. The perfuming composition of claim 8 , wherein said compound (I) is (E,E)-4,8-cyclododecadien-1-one, (Z,E)-4,8-cyclododecadien-1-one, (E,Z)-4,8-cyclododecadien-1-one, (4E,8E)-12-methylcyclododeca-4,8-dienone, (4E,8Z)-12-methylcyclododeca-4,8-dienone, (4Z,8E)-12-methylcyclododeca-4,8-dienone, 2-methylcyclododeca-4,8-dienone or a mixture thereof.

13. A perfuming consumer product comprising:
i) at least one compound of formula (I), as defined in claim 4 ; and
ii) a perfumery consumer base.

14. A perfuming consumer product according to claim 13 , wherein the perfumery consumer base is a perfume, a fabric care product, a body-care product, an air care product or a home care product.

15. A perfuming consumer product according to claim 13 , wherein the perfumery consumer base is a fine perfume, a cologne, an after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a shampoo, a coloring preparation, a hair spray, a vanishing cream, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a wipe, a dish detergent or hard-surface detergent.

16. The perfuming consumer product of claim 13 , wherein one R group is a hydrogen atom and the other is a hydrogen atom or a methyl or ethyl group.

17. The perfuming consumer product of claim 13 , wherein said compound (I) is in the form of a mixture of stereoisomers (4E,8E), (4Z,8E) and (4E,8Z), wherein the w/w ratio (4E,8E)/[(4Z,8E)+(4E,8Z)] is comprised between 20/80 and 1/99, or between 80/20 and 99.5/0.5.

18. The perfuming consumer product of claim 13 , wherein said compound (I) is (E,E)-4,8-cyclododecadien-1-one, (Z,E)-4,8-cyclododecadien-1-one, (E,Z)-4,8-cyclododecadien-1-one, (4E,8E)-12-methylcyclododeca-4,8-dienone, (4E,8Z)-12-methylcyclododeca-4,8-dienone, (4Z,8E)-12-methylcyclododeca-4,8-dienone, 2-methylcyclododeca-4,8-dienone or a mixture thereof.

Assignees

• Firmenich & Cie

Inventors

• Fankhauser Peter

Classifications

• A61Q15/00

  Anti-perspirants or body deodorants (deodorisation of air A61L9/00) · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• C07C49/607

  of a seven-to twelve-membered ring · CPC title

• C11B9/0038 Primary

  the ring containing more than six carbon atoms · CPC title

• A61Q19/002

  Aftershave preparations · CPC title