Pro-fragrance compounds

Patent metadata

Field	Value
Publication number	US-2016122271-A1
Application number	US-201414889858-A
Country	US
Kind code	A1
Filing date	May 5, 2014
Priority date	May 8, 2013
Publication date	May 5, 2016
Grant date	—

Abstract

A compound is provided of Formula (I), wherein R 1 represents a C 3 to C 20 hydrocarbon group derived from an alcohol of formula R 1 OH, from a formate of formula R 1 OCH═O, or a cinnamyl aldehyde of Formula (II) wherein a compound of Formula I is capable of releasing a compound, when oxidized, selected from the group consisting of a fragrant alcohol of formula R 1 OH, a fragrant formate ester of formula R 1 OCH=0 and aryl aldehyde of Formula (III), wherein R 2 is, independently, hydrogen atom, hydroxyl group, optionally substituted C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, or -0(C=0)CH(CH3) 2 wherein any two of R 2 may form an optionally substituted 5 or 6 membered ring. The compounds are useful for example as a precursor for the prolonged delivery or release of fragrant compounds such as fragrant alcohols, fragrant aldehydes or fragrant formates.

First claim

1 - 3 . (canceled)

4 . A compound selected from the group consisting of (E)-(3-(2,6-dimethyloct-7-en-2-yloxy)prop-1-enyl)benzene (E)-(3-(2,6-dimethyloct-7-en-2-yloxy)prop-1-enyl)benzene; (E)-(3-((3-dimethyloct-6-en-1-yl)oxy)prop-1-en-1-yl)benzene; (E)-(3-(cinnamyloxy)butyl)benzene; 1-(3-(2,6-dimethyloct-7-en-2-yloxy)prop-1-enyl)-4-methoxybenzene; 1-(3-(2,6-dimethyloctan-2-yloxy)prop-1-enyl)-4-methoxybenzene; 1-(3-(3,7-dimethylocta-1,6-dien-3-yloxy)prop-1-enyl)-4-methoxybenzene; 1-(3-(3,7-dimethyloct-1-en-3-yloxy)prop-1-enyl)-4-methoxybenzene; 1-methoxy-4-((E)-3-((1RS,2SR)-2-pentylcyclopentyloxy)prop-1-enyl)benzene; 1-(3-((2,6-dimethyloct-7-en-2-yl)oxy)prop-1-en-1-yl)-4-ethylbenzene; 4-(3-(2,6-dimethyloct-7-en-2-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene; (E)-1-methoxy-4-(3-(4-phenylbutan-2-yloxy)prop-1-enyl)benzene; 1-methoxy-4-((E)-3-((E)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-yloxy)prop-1-enyl)benzene; and 1-(3-(3,7-dimethyloct-1-en-3-yloxy)prop-1 -enyl)-4-methoxybenzene.

5 . A method of releasing a fragrant compound from a precursor compound, wherein the fragrant compound is selected from the group consisting of R 1 OH, an aryl aldehyde of Formula (III) and a formate ester of formula R 1 OCH═O:

by exposing a precursor compound of Formula I:

to an environment wherein the compound is oxidized and prolongs or intensifies the perfuming effect of the fragrant compound and wherein:
R 2 is, independently, hydrogen atom, hydroxyl group, —O(C═O)CH(CH3) 2 , optionally substituted C 1 -C 6 alkyl group or C 1 -C 6 alkoxy group, wherein any two of R 2 may form an optionally substituted 5 or 6 membered ring R represents a C 3 to C 20 hydrocarbon group derived from fragrant alcohol of formula R 1 OH, a fragrant formate of formula R 1 OCH═O and an aryl aldehyde of Formula (III).

6 . The method as recited in claim 5 wherein the method comprises the release of at least two compounds from the precursor compound, wherein at least one of the compounds is a fragrant compound wherein the two compounds are the same or different and each independently comprises the formula (III):

7 . The method as recited in claim 5 wherein the C 1 -C 6 alkoxy group is selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy and butoxy group.

8 . The method as recited in claim 7 wherein the C 1 -C 6 alkoxy is methoxy group.

9 . The method as recited in any one of claim 5 wherein the C 1 -C 6 alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, cyclopropyl, cyclopentyl and cyclohexyl group.

10 . A method to improve, enhance or modify odoriferous properties of a perfuming composition or a perfumed article, which method comprises adding to said composition or article an effective amount of a compound of Formula (I) according to claim 5 to improve, enhance or modify the odor of the perfuming composition or perfumed article.

11 . A perfumed article comprising a compound according claim 5 wherein the perfumed article is provided in a perfumed product selected from the group consisting of perfume, cologne, bath gel, shower gel, hair-care product, cosmetic preparation, body deodorant, solid or liquid airfreshener, detergent, fabric softener, and all purpose cleaner.

12 . The perfumed article according to claim 11 wherein the all purpose cleaner is an all purpose household cleaner, a window cleaner, a furniture polish, a fabric conditioner, softener or wash in form of a powder, a liquid or a tablet, a shampoo, a hair conditioner, a leave-in hair conditioner, or a hairspray.

13 . The method as recited in claim 5 wherein a compound of Formula I is exposed to the environment through a perfumed article comprising the compound wherein the perfurmed article is provided in a perfumed product selected from the group consisting of perfume, cologne, bath gel, shower gel, hair-care product, cosmetic preparation, body deodorant, solid or liquid airfreshener, detergent, fabric softener, and all purpose cleaner.

14 . The method as recited in claim 13 wherein the all purpose cleaner is an all purpose household cleaner, a window cleaner, a furniture polish, a fabric. conditioner, softener or wash in form of a powder, a liquid or a tablet, a shampoo, a hair conditioner, a leave-in hair conditioner, or a hairspray.

15 . (canceled)

Assignees

• Firmenich & Cie

Inventors

• Indradas Brinda
• Virtucio Gilbert
• Womack Gary

Classifications

• C07C45/36

  in compounds containing six-membered aromatic rings · CPC title

• C07C43/23

  containing hydroxy or O-metal groups · CPC title

• C11B9/0015

  containing oxygen as the only heteroatom · CPC title

• C07C29/50

  with molecular oxygen only · CPC title

• C07C45/37

  of >C—O—functional groups to >C=O groups · CPC title