# US 10,767,136 B2 · Pro-fragrance compounds

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- Number: US 10,767,136 B2
- Document ID: US10767136B2
- Status: Granted
- Kind: B2
- Application number: 15/351,175
- Filed: 2016-11-14
- Published: 2018-01-18
- Granted: 2020-09-08
- Earliest claimed: 2015-11-13
- Assignees: Firmenich SA
- Applicants: Firmenich SA
- Inventors: Brinda Indradas; Gary B. Womack
- Web page: https://patentgrep.com/patent/US10767136B2

## CPC

- C11B 9/0061: {compounds containing a six-membered aromatic ring not condensed with another ring}
- C07C 43/23: containing hydroxy or O-metal groups
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Precursor or pro-fragrance compounds used as a precursor to deliver at least one fragrant compound that is capable of imparting an odor, in particular one which imparts an odor to a material, more particularly to a fabric or textile. The pro-fragrant compounds of the invention include fragrant alcohols (R1OH) released from a compound of Formula I or in which Formula I is derived from (R1OH) and encompass any fragrant alcohol having more than three carbon atoms. Also, methods of generating the fragrant compounds and to improve, enhance or modify odoriferous properties of a perfuming composition or a perfumed article are also disclosed, as are the resultant perfuming compositions and articles.

## Claims

### Claim 1

A compound of Formula (I)
wherein said compound is capable of releasing upon oxidation an alcohol of formula R1OH selected from the group consisting of anisic alcohol, fenchylic alcohol, 9-decen-1-ol, phenethylol, citronellol 3-methyl-5-phenyl-1-pentanol, (4-isopropylcyclohexyl)methanol, 4-phenylbutan-2-ol, 2,6-dimethyl-7-octen-2-ol, 3,7-dimethyl-2,6-octadien-1-ol, (Z)-3-hexen-1-ol, 2-hexanol, 5-ethyl-2-nonanol, 2,6-nonadien-1-ol, borneol, 1-octen-3-ol, 4-cyclohexyl-2-methyl-2-butanol, 2-methyl-4-phenyl-2-butanol, 2-methyl-1-phenyl-2-propanol, cyclomethylcitronellol, decanol, 8-p-menthanol, 3,7-dimethyl-1-octanol, 2,6-dimethyl-2-heptanol, dodecanol, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, linalool, 2-methoxy-4-propyl-1-cylohexanol, α-terpineol, tetrahydromuguol, 3,7-dimethyl-3-octanol, 5,6-dimethyl-1-methylethenylbicyclo[2.2.1]hept-5-ene-2-methanol, 2-phenyethanol, 1-phenylpropanol, 2-phenylpropanol, (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol, 2,2-dimethyl-3-(3-methylphenyl)-propan-1-ol, 2-pentylcyclopentanol, 1,1-dimethyl-2-phenylethanol, 4-cyclohexyl-2-methylbutan-2-ol, menthol, 2,6-dimethylheptan-2-ol, 2-tert-butylcyclohexanol, 4-tert-butylcyclohexanol, 2,6-dimethyl-3,5-octadien-2-ol, 2-methyl-6-methylene-7-octen-2-ol, 3,7,9-trimethyl-1,6-decadien-3-ol, 3,6-dimethyloctan-3-ol, 1,2-dimethyl-3-prop-1-en-2-ylcyclopentan-1-ol, 2-methyl-4-phenylpentanol, 3-methyl-5-phenylpentanol, 3-methyl-5-(2,2,3-trimethyl-1-cyclopent-3-enyl)pentan-2-ol, (E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol, (E)-4-methyldec-3-en-5-ol, 4-(4-hydroxyphenyl)butan-2-ol, 4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenol, 4-(3-hydroxyprop-1-en-1-yl)-2-ethoxyphenol, 2,6-dimethyloctan-2-ol, 3,7-dimethylnon-1-en-3-ol, wherein:
a) the alcohol of formula R1OH is derived from the
moiety of the compound of Formula (I), such that R1 moiety of the alcohol of formula R1OH corresponds to the R1 moiety of the compound of Formula (I);
b) each R2 is, independently from each other at each position, hydrogen, hydroxyl group, an optionally substituted C1-C6 alkyl group, a C1-C6 alkoxy group, —O(C═O)CH3 or —O(C═O)CH(CH3)2;
c) wherein R2 may form an optionally substituted 5 or 6 membered ring;
d) wherein n=5 provided that R2 is not hydrogen at every position; and
e) provided that Formula I is not 1-(3-isopropoxyprop-1-en-1-yl)-4-methylbenzene, 1-(3-isopropoxyprop-1-en-1-yl)-4-methoxybenzene, 1-butyl-4-(3-isopropoxyprop-1-en-1-yl)benzene, 1-(3-butoxyprop-1-en-1-yl)-4-methylbenzene, 1-(3-butoxyprop-1-en-1-yl)-3-methylbenzene, 2-(3-butoxyprop-1-en-1-yl)-1,3,5-trimethylbenzene, 1-(3-butoxyprop-1-en-1-yl)-4-(tert-butyl)benzene, 1-(3-butoxyprop-1-en-1-yl)-4-methoxybenzene, 1-(3-(tert-butoxy)prop-1-en-1-yl)-4-methylbenzene, 1-(3-(tertbutoxy) prop-1-en-1-yl)-4-methoxybenzene, 1-(3-(tert-butoxy)prop-1-en-1-yl)-4-butylbenzene, (E)-1-(3-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-1-yl)-4-methoxybenzene, 4-(3-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene, 5-(3-propoxyprop-1-en-1-yl)benzo[d][1,3]dioxole, 5-(3-butoxyprop-1-en-1-yl)benzo[d][1,3]dioxole, 5-(3-pentoxyprop-1-en-1-yl) benzo[d][1,3]dioxole, 5-(3-hexyloxyprop-1-en-1-yl)benzo[d][1,3]dioxole, 1-(3-(benzyloxy)prop-1-en-1-yl)-4-methylbenzene, 1-(3-(benzyloxy)prop-1-en-1-yl)-4-methoxybenzene, 2-(3-(benzyloxy)prop-1-en-1-yl)-1,3,5-trimethylbenzene, 1-(3-(benzyloxy)prop-1-en-1-yl)-4-(tert-butyl)benzene, 4-(3-(benzyloxy)prop-1-en-1-yl)-2-methoxyphenol, 4-(3-(benzyloxy)prop-1-en-1-yl)-2-methoxyphenol, 4-(3-(benzyloxy)prop-1-en-1-yl)-2,6-dimethoxyphenol, 2-methoxy-4-(((3-(3,4,5-trimethoxyphenyl)allyl)oxy)methyl)phenol, (E)-5-(3-(benzyloxy)prop-1-en-1-yl)benzo[d][1,3]dioxole, 5-(((3-(benzo[d][1,3]dioxol-5-yl)allyl)oxy)methyl)benzo[d][1,3]dioxole, 1-(3-(cinnamyloxy)prop-1-en-1-yl)-4-methoxybenzene, 4,4′-(oxybis(prop-1-ene-3,1-diyl))bis(methoxybenzene), 4-(3-(cinnamyloxy)prop-1-en-1-yl)-2-methoxyphenol, 5-(3-(cinnamyloxy)prop-1-en-1-yl)-1,2,3-trimethoxybenzene, capsiconiate, or dihydrocapsiconiate.

### Claim 2 (depends on 1)

The compound as recited in claim 1 wherein R2 is hydroxy located at the para position and a methoxy at the meta position and hydrogen at the remaining positions.

### Claim 3 (depends on 1)

The compound as recited in claim 1 wherein at least one R2 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.

### Claim 4 (depends on 3)

The compound as recited in claim 3 wherein at least one R2 is selected from methyl, ethyl and tert-butyl and are located each independently at the meta and/or para positions with hydrogen at the remaining positions.

### Claim 5 (depends on 4)

The compound as recited in claim 4 wherein R2 is ethyl and is located at the para position with hydrogen at the remaining positions.

### Claim 6 (depends on 1)

The compound as recited in claim 1 wherein one or two of the R2 substituents are each independently selected from the group consisting of hydroxyl, methoxy, ethoxy, propoxy, isopropoxy and butoxy group, and R2 is hydrogen at the remaining positions.

### Claim 7 (depends on 6)

The compound as recited in claim 6 wherein a first R2 is a methoxy located at the para and a second R2 is a methoxy located at the meta position, and R2 is hydrogen at the remaining positions.

### Claim 8 (depends on 1)

The compound as recited in claim 1 wherein two R2 groups, located at the para and meta positions, together form a methylenedioxy component of a ring with the carbon atoms to which they are attached.

### Claim 9

A compound of Formula (I)
wherein R1 represents a C3 to C20 optionally substituted linear, branched or cyclic alkyl; a C3 to C20 optionally substituted linear, branched or cyclic alkenyl; or a C3 to C20 optionally substituted linear, branched or cyclic alkynyl group,
wherein a first R2 is a hydroxy located at the para position; a second R2 is a methoxy located at the meta position; and R2 is hydrogen at the remaining positions, and
wherein n is 5.

### Claim 10 (depends on 1)

A method of releasing a fragrant compound from a precursor compound, wherein the fragrant compound is selected from the group consisting of a compound of Formula III
by exposing a precursor compound of Formula I:
to an environment wherein the compound is oxidized and wherein R1 and R2 are as set forth in claim 1.

### Claim 11 (depends on 10)

The method as recited in claim 10 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):
by exposing a precursor compound of Formula I:
to an environment wherein the compound is oxidized.

### Claim 12 (depends on 10)

The method as recited in claim 10 wherein R2 is hydroxy located at the para position and a methoxy at the meta position and hydrogen at the remaining positions.

### Claim 13 (depends on 10)

The method as recited in claim 10 wherein at least one R2 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.

### Claim 14 (depends on 13)

The method as recited in claim 13 wherein at least one R2 is selected from methyl, ethyl and tert-butyl and are located each independently at the meta and/or para positions with hydrogen at the remaining positions.

### Claim 15 (depends on 14)

The method as recited in claim 14 wherein R2 is ethyl and is located at the para position with hydrogen at the remaining positions.

### Claim 16 (depends on 10)

The method as recited in claim 10 wherein one or two of the R2 substituents comprises C1-C6 alkoxy groups selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy and butoxy group and R2 is hydrogen at the remaining positions.

### Claim 17 (depends on 16)

The method as recited in claim 16 wherein R2 is a methoxy located at the para and meta position and R2 is hydrogen at the remaining positions.

### Claim 18 (depends on 17)

The method as recited in claim 17 wherein the alkoxy groups are located at the para and meta position and together form a methylenedioxy ring.

### Claim 19 (depends on 10)

The method as recited in claim 10 wherein R2 is a hydroxyl located at the para position and an ethoxy located at the meta position and R2 is hydrogen at the remaining positions.

### Claim 20 (depends on 10)

The method as recited in claim 10 wherein R1 is an optionally substituted linear, branched or cyclic C3-C20 alkyl.

### Claim 21 (depends on 10)

The method as recited in claim 10 wherein R1 is an optionally substituted linear, branched or cyclic C3-C20 alkenyl.

### Claim 22 (depends on 10)

The method as recited in claim 10 wherein R1 is an optionally substituted linear, branched or cyclic C3-C20 alkynyl.

### Claim 23 (depends on 20)

The method as recited in claim 20 wherein R1 is an optionally substituted linear, branched or cyclic C6 to C12 alkyl.

### Claim 24 (depends on 21)

The method as recited in claim 21 wherein R1 is an optionally substituted linear, branched or cyclic C6 to C12 alkenyl.

### Claim 25 (depends on 22)

The method as recited in claim 22 wherein R1 is an optionally substituted linear, branched or cyclic C6 to C12 alkynyl.

### Claim 26 (depends on 10)

The method as recited in claim 10 wherein the cyclic substituent comprises an oxygen in the ring.

### Claim 27

A compound of the following structure:

### Claim 28 (depends on 6)

The compound as recited in claim 6 wherein the compound of Formula (I), upon oxidation, releases the alcohol of formula R1OH and a compound of formula (III)
wherein one or two of the R2 substituents are each independently selected from the group consisting of hydroxyl, methoxy, ethoxy, propoxy, isopropoxy and butoxy group, and R2 is hydrogen at the remaining positions.

### Claim 29 (depends on 6)

The compound as recited in claim 6 wherein a first R2 is a methoxy located at the meta position, a second R2 is a hydroxyl located at the para position, and R2 is hydrogen at the remaining positions.

### Claim 30 (depends on 1)

The compound as recited in claim 1 wherein the compound of Formula (I), upon oxidation, releases the alcohol of formula R1OH and a compound of formula (III):
a) wherein each R2 is, independently from each other at each position, hydrogen, hydroxyl group, an optionally substituted C1-C6 alkyl group, a C1-C6 alkoxy group, —O(C═O)CH3 or —O(C═O)CH(CH3)2;
b) wherein R2 may form an optionally substituted 5 or 6 membered ring; and
c) wherein n=5 provided that R2 is not hydrogen at every position.