Organic compounds

Patent metadata

Field	Value
Publication number	US-10138195-B2
Application number	US-201415521538-A
Country	US
Kind code	B2
Filing date	Nov 10, 2014
Priority date	Nov 10, 2014
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

A compound represented by the formula I

R 1 is —(CHR 4 ) m —(CHR 5 ) n —(CHR 6 ) o —CHO, with R 4 , R 5 , R 6 being independently selected from H or Me, and with m, n, o being independently selected from 0 and 1; R 2 is H or Me; and R 3 is a C3-C6 branched, linear or cyclic alkenyl residue. Said compounds are useful as perfume ingredients in personal care and household care products.

First claim

The invention claimed is:

1. A compound represented by formula I

wherein
R 1 is —(CHR 4 ) m —(CHR 5 ) n —(CHR 6 ) o —CHO, with R 4 , R 5 , R 6 being independently selected from H or Me, and with m, n, o being independently selected from 0 and 1;
R 2 is Me; and
R 3 is a C3-C6 branched, linear or cyclic alk-2-enyl residue.

2. A pro-perfume, suitable to release at least one compound represented by formula I

wherein
R 1 is —(CHR 4 ) m —(CHR 5 ) n —(CHR 6 ) o —CHO, with R 4 , R 5 , R 6 being independently selected from H or Me, and with m, n, o being independently selected from 0 and 1;
R 2 is Me; and
R 3 is a C3-C6 branched, linear or cyclic alk-2-enyl residue,
the pro-perfume being optionally an aminal and/or enamine of the compound represented by the formula I.

3. A perfume composition comprising the pro-perfume according to claim 2 .

4. The perfume composition according to claim 3 that is free of any aryl-substituted propanal odourants that are unsubstituted on the aryl ring at a position ortho to the substituent bearing the aldehyde functionality.

5. The perfume composition according to claim 3 comprising one or more additional fragrance ingredients, optionally 3-(4-isobutyl-2-methylphenyl)propanal.

6. A personal care or household care composition comprising at least a perfume composition as defined in claim 3 .

7. The personal care or household care composition according to claim 6 , further comprising enzymes.

8. The personal or household care composition according to claim 6 , characterised in that it is a textile treatment product.

9. The personal or household care composition according to claim 6 , characterised in that it is a detergent composition.

10. A method of imparting green odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto a pro-perfume as defined in claim 2 , and selectively excluding from said fine fragrance or consumer product any aryl-substituted alkanal compounds, which are unsubstituted on the ring at the position ortho to the substituent containing aldehyde functionality, said selective addition or exclusion being based on the susceptibility of said compounds to enzymatically-mediated degradation to their benzoic acid derivatives when incubated with hepatocytes isolated from rats, said compounds being suitable for addition on the basis that they do not degrade to their benzoic acid derivatives, whereas said compounds being excluded on the basis that they do degrade to their benzoic acid derivatives.

11. The perfume composition according to claim 3 that is free of 3-(4-tert-butylphenyl)-2-methylpropanal.

12. The compound according to claim 1 wherein R 3 is a C3-C6 branched, linear or cyclic alk-2-enyl residue.

13. The compound according to claim 1 wherein R 3 is a C3-C6 alk-2-enyl residue with an exo-methylene group.

14. The compound according to claim 1 wherein R 3 is a C3-C6 branched, linear or cyclic alk-2-enyl residue carrying a CH 2 group in alpha position to the phenyl ring.

15. The compound according to claim 1 wherein R 3 is selected from the group consisting of allyl, 2-methylallyl, 2-methylenebutyl, 3-methylbut-2-en-1-yl, 3-methylbut-3-en-2-yl and but-2-en-1-yl.

16. A perfume composition comprising at least one compound according to claim 1 .

17. The perfume composition according to claim 16 that is free of any aryl-substituted propanal odourants that are unsubstituted on the aryl ring at a position ortho to the substituent bearing the aldehyde functionality.

18. The perfume composition according to claim 16 that is free of 3-(4-tert-butylphenyl)-2-methylpropanal.

19. The perfume composition according to claim 16 comprising one or more additional fragrance ingredients, optionally 3-(4-isobutyl-2-methylphenyl) propanal.

20. A personal care or household care composition comprising at least one compound as defined in claim 1 .

21. A method of imparting green odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto at least one compound of formula I as defined in claim 1 , and selectively excluding from said fine fragrance or consumer product any aryl-substituted alkanal compounds, which are unsubstituted on the ring at the position ortho to the substituent containing aldehyde functionality, said selective addition or exclusion being based on the susceptibility of said compound of formula I or said ortho unsubstituted compounds to enzymatically-mediated degradation to their benzoic acid derivatives when incubated with hepatocytes isolated from rats, said compound of formula I being suitable for addition on the basis that it does not degrade to its benzoic acid derivatives, whereas said compounds being excluded on the basis that they do degrade to their benzoic acid derivatives.

22. The personal care or household care composition according to claim 20 , further comprising enzymes.

23. The personal or household care composition according to claim 20 , characterised in that it is a textile treatment product.

24. The personal or household care composition according to claim 20 , characterised in that it is a detergent composition.

25. A personal care or household care composition comprising at least a pro-perfume as defined in claim 2 .

26. The personal care or household care composition according to claim 25 , further comprising enzymes.

27. The personal or household care composition according to claim 25 , characterised in that it is a textile treatment product.

28. The personal or household care composition according to claim 25 , characterised in that it is a detergent composition.

Assignees

• Givaudan Sa
• Givaudan Sa

Inventors

• Flachsmann Felix

Classifications

• C07C47/238 Primary

  having unsaturation outside the aromatic rings · CPC title

• C07C47/235 Primary

  containing six-membered aromatic rings and other rings · CPC title

• C11D3/2072

  Aldehydes-ketones · CPC title

• C11B9/0061

  compounds containing a six-membered aromatic ring not condensed with another ring · CPC title

• C11D3/50

  Perfumes · CPC title