Organic compounds

Patent metadata

Field	Value
Publication number	US-9988592-B2
Application number	US-201715484405-A
Country	US
Kind code	B2
Filing date	Apr 11, 2017
Priority date	May 8, 2013
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

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, and is represented by Formula 1

wherein,
R 1 , R 2 , R 3 , R 6 and R 7 each independently may represent H or methyl;
R 4 is H, or when R 5 is H, R 4 is a C 1 -C 7 branched or linear, saturated or unsaturated, unsubstituted or substituted, optionally with cyclopropyl groups, alkyl radical;
R 5 is H, or when R 4 is H, R 5 is a C 1 -C 7 branched or linear, saturated or unsaturated, unsubstituted or substituted, optionally with cyclopropyl groups, alkyl radical; or
R 4 and R 5 together with the carbon atoms to which they are attached, form a substituted or unsubstitued 5-membered ring;
n=0, 1, 2;
the dotted line represents an optional single bond, with the proviso that when the dotted line represents a single bond R 4 or R 5 are sec-butyl, iso-butyl or a C 5 -C 7 branched or linear, saturated or unsaturated alkyl residue; and
wherein the compounds are not selected from 5-(tert-butyl)-2-methyl-2,3-dihydro-1H-indene-2-carbaldehyde, 5-(tert-butyl)-2,3-dihydro-1H-indene-2-carbaldehyde, 5-isopropyl-2,3-dihydro-1H-indene-2-carbaldehyde, 5-isopropyl-2-methyl-2,3-dihydro-1H-indene-2-carbaldehyde, 5-ethyl-2,3-dihydro-1H-indene-2-carbaldehyde, 5-ethyl-2-methyl-2,3-dihydro-1H-indene-2-carbaldehyde, 5-methyl-2,3-dihydro-1H-indene-2-carbaldehyde, 2,5-dimethyl-2,3-dihydro-1 H-indene-2-carbaldehyde, 3-(5-(tert-butyl)-2-methylphenyl)propanal, 3-(5-(tert-butyl)-2-methylphenyl)-2-methyl propanal, 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. 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.

3. 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-methypropanal.

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

5. A personal care or household care composition according to claim 4 containing enzymes.

6. The personal or household care composition according to claim 5 characterised in that it is a textile treatment product.

7. The personal or household care composition according to claim 5 characterised in that it is a detergent composition.

8. 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 degrade to their benzoic acid derivatives.

9. 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 2

wherein R 1 , R 2 , R 3 , and R 6 each independently may represent H or methyl;
R4 is H, or when R 5 is H, R 4 is a C 1 -C 7 branched or linear, saturated or unsaturated, unsubstituted or substituted, optionally with cyclopropyl groups, alkyl radical;
R 5 is H, or when R 4 is H, R 5 is a C 1 -C 7 branched or linear, saturated or unsaturated, unsubstituted or substituted, optionally with cyclopropyl groups, alkyl radical; or R 4 and R 5 together with the carbon atoms to which they are attached, form a substituted or unsubstitued 5-membered ring; and wherein the compounds are 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.

10. A method of utilizing the compound according to claim 9 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.

11. A perfume composition comprising the compound as defined in claim 9 , 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.

12. A personal care or household care composition perfumed with an aryl-substituted alkanal compound according to claim 9 .

13. A personal care or household care composition according to claim 12 containing enzymes.

14. The personal or household care composition according to claim 12 characterised in that it is a textile treatment product.

15. The personal or household care composition according to claim 12 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 9 , 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 be

Assignees

• Givaudan Sa

Inventors

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

Classifications

• C07C47/228

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

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• A61K8/33

  containing oxygen · CPC title

• C07C47/453

  containing six-membered aromatic rings · CPC title

• C11B9/0061 Primary

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