Fragrance precursors

• US 20020077508A1
• Filed: 04/10/2001
• Published: 06/20/2002
• Est. Priority Date: 04/10/2000
• Status: Active Grant

• Current Assignee: Givaudan SA
• Original Assignee: Givaudan SA
• Inventors: Plessis, Caroline, Gautschi, Markus, Derrer, Samuel
• Granted Patent: US 6,492,563 B2
• Time in Patent Office: Days
• US Class Current: 568/336
• CPC Class Codes: C07C 45/64 by introduction of functional groups containing oxygen only in singly bound form
• CPC Class Codes: C07C 45/673 by change of size of the carbon skeleton
• CPC Class Codes: C07C 45/71 being hydroxy groups
• CPC Class Codes: C07C 49/83 polycyclic
• CPC Class Codes: C07C 49/84 containing ether groups, groups, groups, or groups
• CPC Class Codes: C11D 3/507 Compounds releasing perfumes by thermal or chemical activation

Abstract

The present invention is a fragrance precursor of formula I:

for a fragrant ketone of formula II:

and a fragrant ester of formula III:

wherein,

R¹ to R⁵ represent independently H, —NO₂, linear or branched C₁-C₆-alkyl, C₁-C₆-alkenyl, C₁-C₆-alkinyl or C₁-C₄-alkoxy,

R¹ and R², R² and R³, R³ and R⁴, and R⁴ and R⁵ may form together one or two aliphatic or aromatic rings,

R⁶ and R⁷ are independently H, linear or branched C₁-C₆-alkyl-, C₁-C₆-alkenyl, C₁-C₆-alkinyl, and

R⁸ and R⁹ are the residues of an acid R⁸-COOH and an alcohol R⁹OH respectively forming the fragrant ester of formula III. A method for providing an odor by admixing with a product a fragrance precursor as detailed above.

Claims

1. A fragrance precursor of formula I:

2. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of an aliphatic acid having 1 to 4 carbon atoms and R⁹ is the residue of an aliphatic alcohol having 2 to 20 carbon atoms.

3. A fragrance precursor according to claim 1 wherein R⁸ in formula I is -CH₃ and R⁹ is the residue of an aliphatic alcohol having 2 to 20 carbon atoms.

4. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of an aliphatic acid having 5 to 20 carbon atoms and R⁹ is the residue of an aliphatic alcohol having 1 to 5 carbon atoms.

5. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of an aliphatic acid having 5 to 20 carbon atoms and R⁹ is -CH₂CH₃.

6. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of an aliphatic acid having 1 to 4 carbon atoms and R⁹ is the residue of a terpene alcohol having 10 to 20 carbon atoms.

7. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of an aliphatic acid having 1 to 4 carbon atoms and R⁹ is the residue of a monoterpene alcohol.

8. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of a cycloaliphatic acid having 5 to 20 carbon atoms and R⁹ is the residue of an aliphatic alcohol having 1 to 5 carbon atoms.

9. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of a cycloaliphatic acid having 5 to 20 carbon atoms and R⁹ is -CH₂CH₃.

10. A fragrance precursor according to claim 1 wherein R⁸ in formula I is the residue of an aliphatic acid having 1 to 4 carbon atoms and R⁹ is the residue of an araliphatic alcohol having more than 5 carbon atoms.

11. A fragrance precursor according to claim 1 wherein R⁸ in formula I is -CH₃ and R⁹ is the residue of an araliphatic alcohol having more than 5 carbon atoms.

12. A fragrance precursor according to claim 1 wherein at least one of the residues R⁶ and R⁷ in formula I is H.

13. A fragrance precursor according to claim 1 wherein the residues R⁶ and R⁷ in formula I are H.

14. A fragrance precursor according to claim 1 wherein in formula I R⁶ and R⁷ are H and R¹ to R⁵ represent independently H, —

NO₂, linear or branched C₁-C₆-alkyl, C₁-C₆-alkenyl, C₁-C₆-alkinyl or C₁-C₄ alkoxy.

15. A fragrance precursor according to claim 1 wherein the fragrant ketone of formula II is selected from the group consisting of 1-phenyl-ethanone, 2,4-dimethylphenyl-ethanone, 1-[4-(1,1-dimethylethyl)-2,6-dimethylphenyl]-ethanone, 1-(4-tert-butyl-3,5-dinitro-2,6-dimethyl)-ethanone, and 1-(4-methoxyphenyl)-ethanone.

16. A fragrance precursor according to claim 1 wherein in formula I R¹ and R², R² and R³, R³ and R⁴, or R⁴ and R⁵, form together an aliphatic or aromatic ring.

19. A fragrance precursor according to claim 1 wherein the fragrant ketone of formula II is selected from the group consisting of 1-(2-naphtalenyl)-ethanone, 4-acetyl-6-tert-butyl- 1,1 -dimethyl-indan, 1 -(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2-naphthalenyl-ethanone, 1-(5,6,7,8-tetrahydro-3′

, 5′

, 5′

, 8′

, 8′

-pentamethyl-2-naphthalenyl)-ethanone, 1-(5,6,7,8-tetrahydro-3′

-ethyl-5′

, 5′

, 8′

, 8′

-tetramethyl-2-naphthalenyl)-ethanone, 1 -(2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl-ethanone, 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl-1H-inden-5-yl-ethanone, 5-acetyl-1,1,2,3,3-pentamethyl-indane, and 1-(5,6,7,8-tetrahydro-2-naphthalenyl)-ethanone.

20. A compound of formula I:

17. A fragrance precursor according to claim 21 wherein the aliphatic or aromatic ring contains substituted or unsubstituted C₁ -C₄-alkyl, C₁ -C₄-alkenyl, or C₁-C₄-alkinyl residues.

18. A fragrance precursor according to claim 21 wherein the aliphatic or aromatic ring comprises one or more oxygen atoms.

21. A compound according to claim 20 wherein R¹ and R², R² and R³, R³ and R^4, and R⁴ and R⁵ form together one or two aliphatic or aromatic rings and these rings contain linear or branched, substituted or unsubstituted C₁-C₄-alkyl, C₁-C₄-alkenyl or C₁-C₄-alkinyl residues.

22. A compound according to claim 20 wherein the rings comprise one or more oxygen atoms.

23. A compound according to claim 20 wherein R⁶ or R⁷ form with either R¹ or R⁵ a substituted or unsubstituted carbocyclic ring.

25. A composition according to claim 24 wherein the base is selected from the group consisting of a detergent, a fabric softener, a window cleaner, a hard surface cleaner, an all purpose cleaner, a furniture polish, a shampoo, a conditioner, an hairspray, a cosmetic, a sun protection agent, a soap, a bath gel, a shower gel, a deodorant, a perfume, and a cologne.

27. A process according to claim 26 wherein the substrate is selected from the group consisting of fabrics, skin, hair, and hard surfaces.

28. A process according to claim 26 wherein the light is selected from the group consisting of direct sunlight, indirect sunlight, and indoor lighting.

24. A composition comprising a base and a fragrance precursor of formula I:

26. A process for providing a fragrance to a substrate comprising:

(a) contacting a substrate with a composition comprising fragrance precursor of formula I;

wherein,

R¹ to R⁵ represent independently H, —

NO₂, linear or branched C₁-C₆-alkyl, C₁-C₆-alkenyl, C₁-C₆-alkinyl or C₁-C₄-alkoxy,

R¹ and R², R² and R³, R³ and R⁴, and R⁴ and R⁵ may form together one or two aliphatic or aromatic rings,

R⁶ and R⁷ are independently H, linear or branched C₁-C₆-alkyl-, C₁-C₆-alkenyl, C₁-C₆-alkinyl, and

R⁸ and R⁹ are the residues of an acid R⁸ -COOH and an alcohol R⁹OH respectively forming the fragrant ester of formula III; and

(b) exposing the substrate to light to form a fragrant ketone of formula II;

and a fragrant ester of formula III;