Pro-fragrance compounds
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 (R 1 OH) released from a compound of Formula I or in which Formula I is derived from (R 1 OH) 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.
1 . A compound of Formula (I)
wherein said compound is capable of releasing upon oxidation an alcohol of formula R 1 OH 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 R 1 OH is derived from the
moiety of the compound of Formula (I), such that R 1 moiety of the alcohol of formula R 1 OH corresponds to the R 1 moiety of the compound of Formula (I);
b) each R 2 is, independently from each other at each position, hydrogen, hydroxyl group, an optionally substituted C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, —O(C═O)CH 3 or —O(C═O)CH(CH 3 ) 2 ;
c) wherein R 2 may form an optionally substituted 5 or 6 membered ring;
d) wherein n=5 provided that R 2 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.
2 . The compound as recited in claim 1 wherein R 2 is hydroxy located at the para position and a methoxy at the meta position and hydrogen at the remaining positions.
3 . The compound as recited in claim 1 wherein at least one R 2 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
4 . The compound as recited in claim 3 wherein at least one R 2 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.
5 . The compound as recited in claim 4 wherein R 2 is ethyl and is located at the para position with hydrogen at the remaining positions.
6 . The compound as recited in claim 1 wherein one or two of the R 2 substituents are each independently selected from the group consisting of hydroxyl, methoxy, ethoxy, propoxy, isopropoxy and butoxy group, and R 2 is hydrogen at the remaining positions.
7 . The compound as recited in claim 6 wherein a first R 2 is a methoxy located at the para and a second R 2 is a methoxy located at the meta position, and R 2 is hydrogen at the remaining positions.
8 . The compound as recited in claim 1 wherein two R 2 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.
9 . A compound of Formula (I)
wherein R 1 represents a C 3 to C 20 optionally substituted linear, branched or cyclic alkyl; a C 3 to C 20 optionally substituted linear, branched or cyclic alkenyl; or a C 3 to C 20 optionally substituted linear, branched or cyclic alkynyl group,
wherein a first R 2 is a hydroxy located at the para position; a second R 2 is a methoxy located at the meta position; and R 2 is hydrogen at the remaining positions, and
wherein n is 5.
10 . 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 R 1 and R 2 are as set forth in claim 1 .;
wherein the compound of Formula I is capable of releasing upon oxidation an alcohol of formula R 1 OH 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 R 1 OH is derived from the
moiety of the compound of Formula (I), such that R 1 moiety of the alcohol of formula R 1 OH corresponds to the R 1 moiety of the compound of Formula (I);
wherein each R 2 is, independently from each other at each position, hydrogen, hydroxyl group, an optionally substituted C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, —O(C═O)CH 3 or—O(C═O)CH(CH 3 ) 2 ;
wherein R 2 may form an optionally substituted 5 or 6 membered ring;
wherein n=5 provided that R 2 is not hydrogen at every position; and
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-y1)-4-(tert-butyl)benzene, 1-(3-butoxyprop-1-en-1-yl)-4-methoxybenzene, 1-(3-(tert-butoxy)prop-1-en-1-y1)-4-methylbenzene, 1-(3-(tertbutoxy) prop-1-en-1-y1)-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-y1)-4-methoxybenzene, 4-(3-((3,7-dimethyloct-6-en-1-yl)oxy)prop-1-en-1-y1)-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-y1)-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.
11 . 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.
12 . The method as recited in claim 10 wherein R 2 is hydroxy located at the para position and a methoxy at the meta position and hydrogen at the remaining positions.
13 . The method as recited in claim 10 wherein at least one R 2 is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
14 . The method as recited in claim 13 wherein at least one R 2 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.
15 . The method as recited in claim 14 wherein R 2 is ethyl and is located at the para position with hydrogen at the remaining positions.
16 . The method as recited in claim 10 wherein one or two of the R 2 substituents comprises C 1 -C 6 alkoxy groups selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy and butoxy group and R 2 is hydrogen at the remaining positions.
17 . The method as recited in claim 16 wherein R 2 is a methoxy located at the para and meta position and R 2 is hydrogen at the remaining positions.
18 . 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.
19 . The method as recited in claim 10 wherein R 2 is a hydroxyl located at the para position and an ethoxy located at the meta position and R 2 is hydrogen at the remaining positions.
20 . The method as recited in claim 10 wherein R 1 is an optionally substituted linear, branched or cyclic C 3 -C 20 alkyl.
21 . The method as recited in claim 10 wherein R 1 is an optionally substituted linear, branched or cyclic C 3 -C 20 alkenyl.
22 . The method as recited in claim 10 wherein R 1 is an optionally substituted linear, branched or cyclic C 3 -C 20 alkynyl.
23 . The method as recited in claim 20 wherein R 1 is an optionally substituted linear, branched or cyclic C 6 to C 12 alkyl.
24 . The method as recited in claim 21 wherein R 1 is an optionally substituted linear, branched or cyclic C 6 to C 12 alkenyl.
25 . The method as recited in claim 22 wherein R 1 is an optionally substituted linear, branched or cyclic C 6 to C 12 alkynyl.
26 . The method as recited in claim 10 wherein the cyclic substituent of the fragrant compound comprises an oxygen in the ring of Formula III.
27 . A compound of the following structure:
28 . The compound as recited in claim 6 wherein the compound of Formula (I), upon oxidation, releases the alcohol of formula R 1 OH and a compound of formula (III)
wherein one or two of the R 2 substituents are each independently selected from the group consisting of hydroxyl, methoxy, ethoxy, propoxy, isopropoxy and butoxy group, and R 2 is hydrogen at the remaining positions.
29 . The compound as recited in claim 6 wherein a first R 2 is a methoxy located at the meta position, a second R 2 is a hydroxyl located at the para position, and R 2 is hydrogen at the remaining positions.
30 . The compound as recited in claim 1 wherein the compound of Formula (I), upon oxidation, releases the alcohol of formula R 1 OH and a compound of formula (III):
a) wherein each R 2 is, independently from each other at each position, hydrogen, hydroxyl group, an optionally substituted C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, —O(C═O)CH 3 or —O(C═O)CH(CH 3 ) 2 ;
b) wherein R 2 may form an optionally substituted 5 or 6 membered ring; and
c) wherein n=5 provided that R 2 is not hydrogen at every position.
31. The compound as recited in claim 1 wherein the compound is (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-y1)-2-methoxyphenol or (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene.
32. The compound as recited in claim 9 wherein the compound is (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-y1)-2-methoxyphenol.
33. The compound as recited in claim 9 wherein said compound is capable of releasing upon oxidation an alcohol of formula R 1 OH wherein:
the alcohol of formula R 1 OH is derived from the
moiety of the compound of Formula (I), such that the R 1 moiety of the alcohol of formula R 1 OH corresponds to the R 1 moiety of the compound of Formula (I).
34. The method as recited in claim 10 wherein the precursor compound of Formula I is (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-2-methoxyphenol or (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene.
35. The method as recited in claim 11 wherein the precursor compound of Formula I is (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-2-methoxyphenol or (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene.
36. The compound as recited in claim 30 wherein the compound of Formula (I) is (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-2-methoxyphenol or (E)-4-(3-((2,6-dimethyloctan-2-yl)oxy)prop-1-en-1-yl)-1,2-dimethoxybenzene.