Cyclic compounds and their use as precursors of fragrant alcohols

Abstract

Compounds of the formula: in which the dotted lines indicate the position of single or double bonds, R 1 represents a radical belonging to a fragrant alcohol of the formula R 1 OH, X represents a nucleophilic group selected from the group consisting of —OH, ═O, —NH 2 or —NHR 3 , R 3 representing a C 1 to C 6 staight-chain or branched hydrocarbon radical, saturated or unsaturated, or an aliphatic or aromatic ring having 5 or 6 carbon atoms, m and n define whole numbers within the range 0 to 2 such that the sum m+n is equal to 1 or 2, p defines a whole number with a value of 0 or 1, each of the symbols R 2 , R 4 , R 5 , R 6 , R 7 , taken independently, represents a hydrogen atom, a C 1 to C 4 staight-chain or branched hydrocarbon radical, saturated or unsaturated, optionally substituted, and, taken two by two, they can form aromatic or aliphatic monoclic, bicyclic or tricyclic substances with the carbon atoms to which they are bound. Such compounds are capable of releasing a fragrant alcohol of the formula R 1 OH upon hydrolysis of the ester bond.

1 . A compound of formula  
       
         
           
           
               
               
           
         
       
       in which the dotted lines indicate the position of single or double bonds, R 1  represents a radical belonging to a fragrant alcohol of the formula R 1 OH, X represents a nucleophilic group selected from the group consisting of —OH, ═O, —NH2 or —NHR 3 , R 3  representing a C 1  to C 6  straight-chain or branched hydrocarbon radical, saturated or unsaturated, or an aliphatic or aromatic ring having 5 or 6 carbon atoms, m and n define whole numbers within the range 0 to 2 such that the sum m+n is equal to 1 or 2, p defines a whole number with a value of 0 or 1, each of the symbols R 2 , R 4 , R 5 , R 6 , R 7 , taken independently, represents a hydrogen atom, a C 1  to C 4  straight-chain or branched hydrocarbon radical, saturated or unsaturated, optionally substituted, and, taken two by two, they can form aromatic or aliphatic monocyclic, bicyclic or tricyclic substances with the carbon atoms to which they are bound, provided that menthyl 2-acetylbenzoate, benzyl 2-formylbenzoate, octyl 2-formylbenzoate, benzyl 2-acetylbenzoate and menthyl 2-formylbenzoate are excluded.  
     
     
         2 . A compound according to  claim 1 , characterised in that it is capable of assuming a constrained conformation in which the distance between the oxygen or nitrogen of the nucleophilic group X and the carbon of the ester function does not exceed 2.8 Angström for a molecular energy calculated by the method MM2 which differs by no more than 3 kcal/mol from the minimum total energy of the molecule.  
     
     
         3 . A compound according to  claim 1 , characterised in that X represents an ═O group.  
     
     
         4 . A compound according to  claim 3 , characterised in that R 2  defines a hydrogen or a methyl group.  
     
     
         5 . A compound of the formula  
       
         
           
           
               
               
           
         
       
       in which the symbols R 1 , R 2  and R 4  to R 7  are defined as in  claim 1 .  
     
     
         6 . A compound selected from the group consisting of 3,7-dimethyl-6-octenyl 2-formylbenzoate, (E or Z)-3,7-dimethyl-2,6-octadienyl 2-formylbenzoate, 2-phenylethyl 2-formylbenzoate, (E)-3,7-dimethyl-2,6-octadienyl 2-acetylbenzoate and 3,7-dimethyl-6-octenyl 2-acetylbenzoate.  
     
     
         7 . A compound according to  claim 1 , characterised in that X represents an —OH group.  
     
     
         8 . A compound of the formula  
       
         
           
           
               
               
           
         
       
       in which the symbols R 1 , R 2  and R 4  to R 7  are defined as in  claim 1 .  
     
     
         9 . A compound selected from the group consisting of 3-p-menthanyl 2-hydroxymethylbenzoate, 3,7-dimethyl-6-octenyl 2-hydroxymethylbenzoate, 2-phenylethyl 2-hydroxymethylbenzoate, (Z)-3-hexenyl 2-hydroxymethylbenzoate, (E)-3,7-dimethyl-2,6-octadienyl 2-hydroxymethylbenzoate, 1-p-menthen-8-yl 2-hydroxymethylbenzoate, 1,2,2-trimethyl4(2′,2′,3′-trimethyl-3′-cyclopenten-1′-yl)-3-butenyl 2-hydroxymethylbenzoate, (Z)-3-hexenyl dihydrocoumarate, (E)-3,7-dimethyl-2,6-octadienyl dihydrocoumarate and (Z)-3-hexenyl 3-endo-hydroxymethyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylate.  
     
     
         10 . A compound according to  claim 1 , characterised in that the residue of the said compound following release of the perfuming alcohol is odourless.  
     
     
         11 . A perfuming composition or perfumed article containing as an active ingredient a compound of the formula  
       
         
           
           
               
               
           
         
       
       in which the dotted lines indicate the position of single or double bonds, R 1  represents a radical derived from a fragrant alcohol of the formula R 1 OH, X represents one of the nucleophilic groups —OH, ═O, —NH 2  or —NHR 3 , R 3  representing a C 1  to C 6  straight-chain or branched hydrocarbon radical, saturated or unsaturated, or an aliphatic or aromatic ring having 5 or 6 carbon atoms, m and n define whole numbers within the range 0 to 2 such that the sum m+n is equal to 1 or 2, p defines a whole number with a value of 0 or 1, each of the symbols R 2 , R 4 , R 5 , R 6 , R 7 , taken independently, represents a hydrogen atom, a C 1  to C 4  straight-chain or branched hydrocarbon radical, saturated or unsaturated, optionally substituted and, taken two by two, they can form aromatic or aliphatic monocyclic, bicyclic or tricyclic substances with the carbon atoms to which they are bound.  
     
     
         12 . A perfuming composition or perfumed article according to  claim 11 , characterised in that the compound of the formula (I) is capable of assuming a constrained conformation in which the distance between the oxygen or nitrogen of the nucleophilic group X and the carbon of the esteric fimction does not exceed 2.8 Angström for a molecular energy calculated by the method MM2 which differs by no more than 3 kcal/mol from the minimum total energy of the molecule.  
     
     
         13 . A perfuming composition or perfumed article according to  claim 11 , characterised in that in the formula (I) X represents a ═O group.  
     
     
         14 . A perfuming composition or perfumed article according to  claim 13 , characterised in that in the formula (I) R 2  defines a hydrogen or a methyl group.  
     
     
         15 . A perfuming composition or perfumed article according to  claim 11 , characterised in that the compound of formula (I) has the formula:  
       
         
           
           
               
               
           
         
       
       in which the symbols R 1 , R 2 , and R 4  to R 7  are as defined above.  
     
     
         16 . A perfumed article according to  claim 11 , in the form of an after-shave lotion, a cosmetic preparation, a soap, a shampoo, conditioner, or other hair-care product, a bath or shower gel, a foam bath, a body deodorant, an air freshener, a detergent, a textile softener, or an all-purpose cleaner.  
     
     
         17 . A process for perfuming textiles subjected to washing in the presence of a detergent followed optionally by a treatment with a textile softener, the process being characterised in that the detergent or softener contains a compound of formula (I) as defined in  claim 11 .  
     
     
         18 . A process according to  claim 17 , characterised in that the detergent or softener contains a compound of formula (I) wherein X represents a ═O or —OH group.  
     
     
         19 . A process for prolonging the effect of diffusion of the characteristic odour of a fragrant alcohol developed by textiles, characterised in that these textiles are subjected to a washing cycle in the presence of a detergent and optionally to a subsequent treatment with a textile softener, wherein the detergent or softener contains a compound of formula (I) as defined in  claim 11 .  
     
     
         20 . A process according to  claim 19 , characterised in that the detergent or softener contains a compound of formula (I) wherein X represents a ═O or —OH group.