Organic compounds

Patent metadata

Field	Value
Publication number	US-9656938-B2
Application number	US-201414888887-A
Country	US
Kind code	B2
Filing date	May 8, 2014
Priority date	May 8, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

An aryl-substituted alkanal compound having a molecular weight of less than 300 g/mol and which bears a substituent on the aryl ring ortho to a substituent bearing the aldehyde functionality. Said compounds are useful as perfume ingredients in personal care and household care products.

First claim

The invention claimed is:

1. An aryl-substituted alkanal compound having a molecular weight of less than 300 g/mol and which bears a substituent on the aryl ring ortho to a substituent bearing the aldehyde functionality, represented by formula 3

wherein
R 1 , R 2 , and R 3 each independently represent H or methyl;
R 4 is H, or when R 5 is H, R 4 is an iso-butyl, sec-butyl or linear, saturated or unsaturated, unsubstituted or substituted, optionally with cyclopropyl groups, C 5 -C 7 alkyl or alkenyl residue; and
R 5 is H, or when R 4 is H, R 5 is an iso-butyl, sec-butyl or linear, saturated or unsaturated, unsubstituted or substitute, optionally with cyclopropyl groups,C 5 -C 7 alkyl or alkenyl substituent;
or at least one compound selected from 5-isobutyl-2,3-dihydro-1H-indene-2-carbaldehyde and 3-(1,1,6-trimethyl-2,3-dihydro-1H-inden-5-yl)propanal;
and wherein said aryl-substituted alkanal compound is not 3-(5-(tert-butyl)-2-methylphenyl)propanal, 3-(5-(tert-butyl)-2-methylphenyl)-2-methylpropanal, 3-(5-isopropyl-2-methylphenyl)propanal, 3-(5-isopropyl-2-methylphenyl)-2-methylpropanal, 3-(5-ethyl-2-methylphenyl)propanal, 3-(5-ethyl-2-methylphenyl)-2-methylpropanal, 3-(4-(tert-butyl)-2-methylphenyl)propanal, 3-(4-(tert-butyl)-2-methylphenyl)-2-methylpropanal, 3-(4-isopropyl-2-methylphenyl)propanal, 3-(4-isopropyl-2-methylphenyl)-2-methylpropanal, 3-(4-ethyl-2-methylphenyl)propanal, 3-(4-ethyl-2-methylphenyl)-2-methylpropanal, or a compound of formula 3
wherein R 1 through R 5 is independently H or methyl.

2. The compound according to claim 1 represented by formula 4

wherein
R 1 and R 2 , each independently may represent H or methyl; and
R 4 represents an iso-butyl or sec-butyl group, or a saturated or unsaturated C 5 -C 7 alkyl or alkenyl radical, which may be unsubstituted or substituted, optionally with cyclopropyl groups.

3. The compound according to claim 1 represented by formula 5

wherein
R 1 , R 2 , and R 3 each independently may represent H or methyl; and
R 5 is an iso-butyl or sec-butyl group, or a saturated or unsaturated C 5 -C 7 alkyl or alkenyl residue, which may be unsubstituted or substituted, optionally with cyclopropyl groups.

4. The compound according to claim 1 represented by the formula

5. The compound according to claim 1 selected from the group consisting of 3-(4-isobutyl-2-methylphenyl)propanal, 3-(4-isobutyl-2,6-dimethylphenyl)propanal, 3-(4-isobutyl-2-methylphenyl)-2-methylpropanal, 3-(4-isobutyl -2-methyl phenyl)butanal, 3-(4-(sec-butyl)-2-methylphenyl)propanal, 3-(2-methyl-4-(tert -pentyl)phenyl)propanal, 3-(4-isopentyl-2-methylphenyl)propanal, 3-(2-methyl-4-(4-methylpentyl)phenyl)propanal, 3-(2-methyl-5-(4-methylpentyl)phenyl)propanal, 3-(5-isopentyl-2-methylphenyl)propanal, 3-(5-isopentyl-2-methylphenyl)-2-methylpropanal, 3-(5-isobutyl-2-methylphenyl)-2-methylpropanal, 2-methyl-3-(2-methyl-5-(4-methylpentyl)phenyl)propanal, 3-(5-isobutyl-2-methylphenyl)propanal, 3-(2-methyl-4-(2-methylbutyl)phenyl)propanal, 5-isobutyl-2,3-dihydro-1H-indene-2-carbaldehyde, and 3-(1,1,6-trimethyl-2,3-dihydro-1H-inden-5-yl)propanal.

6. A method of utilizing the compound according to claim 1 as a perfume ingredient exhibiting muguet odour characteristics to a personal care or household care composition comprising the step of adding to said composition the compound or a perfume composition containing said compound.

7. A perfume composition comprising the compound as defined in claim 1 , which composition is free of any aryl-substituted alkanal, optionally 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, and optionally free of 3-(4-tert-butylphenyl)-2-methylpropanal.

8. A personal care or household care composition perfumed with an aryl-substituted alkanal compound according to claim 1 .

9. The personal care or household care composition according to claim 8 perfumed with a compound represented by formula 4

wherein
R 1 and R 2 , each independently may represent H or methyl; and
R 4 represents an iso-butyl or sec-butyl group, or a saturated or unsaturated C 5 -C 7 alkyl or alkenyl residue, which may be unsubstituted or substituted, optionally with cyclopropyl groups.

10. The personal care or household care composition according to claim 8 perfumed with a compound represented by formula 5

wherein
R 1 , R 2 , and R 3 each independently may represent H or methyl; and
R 5 is a an iso-butyl or sec-butyl group, or a saturated or unsaturated C 5 -C 7 alkyl or alkenyl radical, which may be unsubstituted or substituted, optionally with cyclopropyl groups.

11. The personal care or household care composition according to claim 8 perfumed with a compound represented by the formula

12. The personal care or household care composition according to claim 8 perfumed with a compound selected from the group consisting of 3-(4-isobutyl-2-methylphenyl)propanal, 3-(4-isobutyl-2,6-dimethylphenyl)propanal, 3-(4-isobutyl-2-methylphenyl)-2-methylpropanal, 3-(4-isobutyl-2-methylphenyl)butanal, 3-(4-(sec-butyl) -2-methylphenyl)propanal, 3-(2-methyl-4-(tert-pentyl)phenyl)propanal, 3-(4-isopentyl-2-methylphenyl)propanal, 3-(2-methyl-4-(4-methylpentyl)phenyl)propanal, 3-(2-methyl-5-(4-methylpentyl)phenyl)propanal, 3-(5-isopentyl-2-methylphenyl)propanal, 3-(5-isopentyl -2-methylphenyl)-2-methylpropanal, 3-(5-isobutyl-2-methylphenyl)-2-methylpropanal, 2-methyl-3-(2-methyl-5-(4-methylpentyl)phenyl)propanal, 3-(5-isobutyl-2-methylphenyl)propanal, 3-(2-methyl-4-(2-methylbutyl)phenyl)propanal, 5-isobutyl-2,3-dihydro-1H-indene-2-carbaldehyde, and 3 (1,1,6-trimethyl-2,3-dihydro-1H-inden-5-yl)propanal.

13. A personal care or household care composition according to claim 8 containing enzymes.

14. The personal or household care composition according to claim 13 characterised in that it is a textile treatment product.

15. The personal or household care composition according to claim 13 characterised in that it is a detergent composition.

16. A method of imparting muguet odour characteristics to a fine fragrance or consumer product comprising the step of adding thereto an aryl-substituted alkanal compound 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 de

Assignees

• Givaudan Sa
• Givaudan Sa

Inventors

• Goeke Andreas
• Kraft Philip
• Laue Heike
• Zou Yue
• Voirol Francis

Classifications

• C07C47/453

  containing six-membered aromatic rings · CPC title

• C07C47/11

  monocyclic · CPC title

• C07C47/228

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

• A61K8/33

  containing oxygen · CPC title

• C11D3/50

  Perfumes · CPC title