Phenyl based compounds substituted with aldehyde moieties and their use in perfumery

Patent metadata

Field	Value
Publication number	US-10443018-B2
Application number	US-201515516810-A
Country	US
Kind code	B2
Filing date	Oct 9, 2015
Priority date	Nov 10, 2014
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

A compound represented by the formula 1

wherein
R 1 is H, or when R 2 and R 3 is H, then R 1 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl;
R 2 is H, or when R 1 and R 3 is H, then R 2 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl;
R 3 is H, or when R 1 and R 2 is H, then R 3 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl; and
R 4 is methyl or a branched or linear, saturated or unsaturated, unsubstituted or substituted (optionally with cyclopropyl groups), C 2 -C 7 alkyl or alkenyl residue, preferentially isobutyl, isoamyl.

Said compounds are useful as perfume ingredients in personal care and household care products.

First claim

The invention claimed is:

1. A compound according to formula 1

wherein
R 1 is H;
R 2 is H, or when R 1 and R 3 is H, then R 2 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl;
R 3 is H, or when R 1 and R 2 is H, then R 3 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl;
and
R 4 is a branched or linear, saturated or unsaturated, unsubstituted or substituted residue, or a C 2 -C 7 alkyl or alkenyl residue.

2. The compound according to claim 1 which is a perfume ingredient.

3. The compound of claim 2 , which exhibits green odour characteristics.

4. A pro-perfume, which releases the compound represented by the formula 1

wherein
R 1 is H;
R 2 is H, or when R 1 and R 3 is H, then R 2 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl;
R 3 is H, or when R 1 and R 2 is H, then R 3 is CHR 5 CHR 6 CHO, CR 5 ═CR 6 CHO or C(CH 3 )CHO, wherein R 5 , R 6 each independently may represent H or methyl; and
R 4 is a branched or linear, saturated or unsaturated, unsubstituted or substituted residue, C 2 -C 7 alkyl or alkenyl residue.

5. The pro-perfume of claim 4 , which is an imine, aminal, hemi-aminal or enamine of the compound according to formula I.

6. The pro-perfume of claim 4 which is a perfume ingredient.

7. The pro-perfume of claim 6 which exhibits green odor characteristics.

8. A perfume composition comprising the pro-perfume of claim 4 .

9. A personal care or household care composition comprising at least a pro-perfume as defined in claim 4 .

10. A method of imparting muguet odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto a pro-perfume as defined in claim 4 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. A perfume composition comprising a compound according to claim 1 .

12. A perfume composition according to claim 11 that is substantially 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.

13. A perfume composition according to claim 11 comprising one or more additional fragrance ingredients.

14. A perfume composition according to claim 13 which comprises 3-(4-isobutyl-2-methylphenyl)propanal.

15. A personal care or household care composition comprising at least a perfume composition according to claim 11 .

16. A perfume composition according to claim 11 that is substantially free of LILIAL.

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

18. A personal care or household care composition according to claim 17 , further comprising enzymes.

19. A personal or household care composition according to claim 17 , which is a textile treatment product.

20. A personal or household care composition according to claim 17 which is a detergent composition.

21. A method of imparting muguet odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto a compound 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 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.

Assignees

• Givaudan Sa

Inventors

• Baumgartner Corinne
• Zou Yue

Classifications

• C11D3/50

  Perfumes · CPC title

• C11B9/0061 Primary

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

• C07C47/228 Primary

  containing six-membered aromatic rings, e.g. phenylacetaldehyde · CPC title

• C11B9/0034

  the ring containing six carbon atoms · CPC title