Pro-fragrance 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 (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.

What is claimed is: 
     
         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.