Organic compounds

Patent metadata

Field	Value
Publication number	US-10119097-B2
Application number	US-201415516828-A
Country	US
Kind code	B2
Filing date	Nov 10, 2014
Priority date	Nov 10, 2014
Publication date	Nov 6, 2018
Grant date	Nov 6, 2018

Abstract

A fragrance precursor represented by the formula 1

wherein
X and Y together represent a double bond to a carbon atom bearing R 1 and R 2 , with R 1 ═H, methyl, acetyl or C 1 -C 3 alkoxycarbonyl (e.g. ethoxycarbonyl); and R2=phenyl optionally substituted with up to 3 (i.e. 0, 1, 2 or 3) groups selected from C 1 -C 4 alkyl (e.g. methyl, ethyl, iso-propyl, tert-butyl), vinyl, hydroxy, C 1 -C 3 alkoxy (e.g. ethoxy), and —O—CH 2 —O—, e.g. R 2 is benzo[d][1,3]dioxol-5-yl, 4-methylphenyl, 4-methoxyphenyl, 4-vinylphenyl or 3-ethoxy-4-hydroxyphenyl or R2=naphthyl, (naphthyl)methyl, 1,1,2,4,4,8-hexamethyl-1,2,3,4-tetrahydronaphthalen-7-yl, or 1,1,2,4,4,-pentamethyl-1,2,3,4-tetrahydronaphthalen-7-yl or R2=COR3, wherein R3 is H, C1-C10 alkoxy (e.g. ethoxy, 1-(3,3-dimethylcyclohexyl)ethoxy), C1-C4 alkyl (e.g. methyl, ethyl, propyl, iso-propyl, tert-butyl), e.g. R2 is formyl, acetyl, ethoxycarbonyl, 1-(3,3-dimethylcyclohexyl)ethoxycarbonyl; or wherein X is OR4, with R4 being H or alkyl, and Y is OR5, with R5 being alkyl, useful as a perfume ingredient.

First claim

The invention claimed is:

1. A fragrance precursor according to the formula 1

wherein
X and Y together represent a double bond to a carbon atom bearing R 1 and R 2 ,
R 1 is H, methyl, acetyl or C 1 -C 3 alkoxy carbonyl, and
R 2 is phenyl optionally substituted with up to 3 groups selected from C 1 -C 4 alkyl, vinyl, hydroxy, C 1 -C 3 alkoxy, and —O—CH 2 —O—, or
R 2 is naphthyl, (naphthyl)methyl, 1,1,2,4,4,8-hexamethyl-1,2,3,4-tetrahydronaphthalen-7-yl, or 1,1,2,4,4,-pentamethyl-1,2,3,4-tetrahydronaphthalen-7-yl or
R 2 is COR 3 , wherein R 3 is H, C 1 -C 10 alkoxy, or C 1 -C 4 alkyl;
or wherein
X is OR 4 , wherein R 4 is H or alkyl, and
Y is OR 5 , wherein R 5 is alkyl.

2. A fragrance precursor according to claim 1 selected from the group consisting of:
ethyl 2-acetyl-5-(4-isobutyl-2-methylphenyl)pent-2-enoate, and,
4-isobutyl-1-(4-(4-methoxyphenyl)but-3-en-l-yl)-2-methylbenzene.

3. A perfume composition comprising a fragrance precursor according to claim 2 .

4. The perfume ingredient according to claim 3 which is adapted to release an ingredient with muguet odour characteristics.

5. A perfume composition comprising a fragrance precursor according to claim 2 .

6. A personal care or household care composition comprising a fragrance precursor according to claim 2 .

7. A method of imparting a muguet odour characteristic to a perfume composition comprising the step of: adding to said composition at least a fragrance precursor according to claim 2 .

8. A perfume ingredient comprising a fragrance precursor according to claim 1 .

9. The perfume ingredient according to claim 8 which is adapted to release an ingredient with muguet odour characteristics.

10. A perfume composition comprising a fragrance precursor according to claim 1 .

11. A perfume composition according to claim 10 that is free of aryl-substituted propanals, that are unsubstituted on the aryl ring at a position ortho to the substituent bearing the aldehyde functionality.

12. A perfume composition according to claim 10 which further comprises 3-(4-isobutyl-2-methylphenyl) propanal.

13. A perfume composition according to claim 10 comprising one or more additional fragrance ingredients.

14. A perfume composition according to claim 10 , which is adapted to release an ingredient with muguet odour characteristics.

15. A personal care or household care composition comprising a fragrance precursor according to claim 1 .

16. A method of imparting a muguet odour characteristic to a perfume composition comprising the step of: adding to said composition at least a fragrance precursor according to claim 1 .

17. The fragrance precursor of claim 1 , wherein R 2 is benzo[d][1,3]dioxo-5-yl, 4-methylphenyl, 4-methoxyphenyl, 4-vinylphenyl or 3-ethoxy-4-hydroxyphenyl.

18. The fragrance precursor of claim 1 , wherein R 2 is formyl, acetyl, ethoxycarbonyl, or 1-(3,3-dimethylcyclohexyl)ethoxycarbonyl.

Assignees

• Givaudan Sa
• Givaudan Sa

Inventors

• Baumgartner Corinne
• Flachsmann Felix

Classifications

• C11D3/507

  Compounds releasing perfumes by thermal or chemical activation · CPC title

• C07C43/205

  the aromatic ring being a non-condensed ring · CPC title

• C07C69/738 Primary

  Esters of keto-carboxylic acids {or aldehydo-carboxylic acids} · CPC title

• C11B9/0061 Primary

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

• C07C43/215

  having unsaturation outside the six-membered aromatic rings · CPC title