Method for releasing aldehyde or ketone

Abstract

The invention relates to a method for releasing an aldehyde or ketone of formula (2) by allowing a hydrolase to act on a compound of formula (1). The compound of formula (1) is used as a flavor or fragrance precursor. In formula (1), each of R 1 , R 2 and R 3 independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent. R 1 and R 2 or R 1 and R 3 may form a ring. Ar represents an aryl group which may have a substituent. In formula (2), R 1 , R 2 and R 3 have the same definitions as those in formula (1). R 1 and R 2 or R 1 and R 3 may form a ring:

1 . A method for releasing an aldehyde or ketone represented by formula (2) by allowing a hydrolase to act on a compound represented by formula (1), in which the compound represented by formula (1) is used as a flavor or fragrance precursor: 
       
         
           
           
               
               
           
         
         wherein in formula (1), each of R 1 , R 2  and R 3  independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1  and R 2  or R 1  and R 3  may form a ring, and Ar represents an aryl group which may have a substituent, and: 
       
       
         
           
           
               
               
           
         
         wherein in formula (2), R 1 , R 2  and R 3  have the same definitions as those in formula (1), and R 1  and R 2  or R 1  and R 3  may form a ring. 
       
     
     
         2 . The method for releasing an aldehyde or a ketone according to  claim 1 , wherein the hydrolase is lipase. 
     
     
         3 . The method for releasing an aldehyde or a ketone according to  claim 1 , wherein each of R 1 , R 2  and R 3  is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent. 
     
     
         4 . A deodorizing method including allowing a microorganism to act on a compound represented by formula (1) to release, as a deodorizing component, an aldehyde or ketone represented by formula (2) and mitigating an odor caused by microorganism: 
       
         
           
           
               
               
           
         
         wherein in formula (1), each of R 1 , R 2  and R 3  independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1  and R 2  or R 1  and R 3  may form a ring, and Ar represents an aryl group which may have a substituent, and: 
       
       
         
           
           
               
               
           
         
         wherein in formula (2), R 1 , R 2  and R 3  have the same definitions as those in formula (1), and R 1  and R 2  or R 1  and R 3  may form a ring. 
       
     
     
         5 . The deodorizing method according to  claim 4 , wherein the microorganism is at least one selected from the group consisting of  Staphylococcus  bacteria,  Corynebacterium  bacteria,  Propionibacterium  bacteria,  Pseudomonas  bacteria,  Bacillus  bacteria,  Moraxella  bacteria, and  Malassezia  fungi. 
     
     
         6 . The deodorizing method according to  claim 4 , wherein each of R 1 , R 2  and R 3  is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent. 
     
     
         7 . A compound represented by formula (3): 
       
         
           
           
               
               
           
         
         wherein in formula (3), a wavy line represents either one of E and Z geometric isomers or a mixture thereof. 
       
     
     
         8 . A compound represented by formula (4): 
       
         
           
           
               
               
           
         
         wherein in formula (4), a wavy line represents either one of E and Z geometric isomers or a mixture thereof. 
       
     
     
         9 . A flavor or fragrance composition containing a compound represented by formula (1): 
       
         
           
           
               
               
           
         
         wherein in formula (1), each of R 1 , R 2  and R 3  independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1  and R 2  or R 1  and R 3  may form a ring, and Ar represents an aryl group which may have a substituent. 
       
     
     
         10 . The flavor or fragrance composition according to  claim 9 , wherein each of R 1 , R 2  and R 3  is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent. 
     
     
         11 . A flavor or fragrance composition containing the compound according to  claim 7 . 
       
         
           
           
               
               
           
         
       
     
     
         12 . A flavor or fragrance composition containing the compound according to  claim 8 . 
       
         
           
           
               
               
           
         
       
     
     
         13 . An aroma product, a laundry care product, a hair care product, a cosmetic, a cleaner or a deodorant, containing a compound represented by formula (1): 
       
         
           
           
               
               
           
         
         wherein in formula (1), each of R 1 , R 2  and R 3  independently represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent, R 1  and R 2  or R 1  and R 3  may form a ring, and Ar represents an aryl group which may have a substituent. 
       
     
     
         14 . The aroma product, laundry care product, hair care product, cosmetic, cleaner or deodorant according to  claim 13 , wherein each of R 1 , R 2  and R 3  is independently a hydrogen atom, an alkyl group having 1 to 13 carbon atoms, which may have a substituent, or an alkenyl group having 2 to 13 carbon atoms, which may have a substituent. 
     
     
         15 . An aroma product, a laundry care product, a hair care product, a cosmetic, a cleaner or a deodorant, containing the compound according to  claim 7 . 
       
         
           
           
               
               
           
         
       
     
     
         16 . An aroma product, a laundry care product, a hair care product, a cosmetic, a cleaner or a deodorant, containing the compound according to  claim 8 , 
       
         
           
           
               
               
           
         
       
     
     
         17 . An aroma product, a laundry care product, a hair care product, a cosmetic, a cleaner or a deodorant, containing the flavor or fragrance composition according to  claim 9 . 
     
     
         18 . An aroma product, a laundry care product, a hair care product, a cosmetic, a cleaner or a deodorant, containing the flavor or fragrance composition according to  claim 11 . 
     
     
         19 . An aroma product, a laundry care product, a hair care product, a cosmetic, a cleaner or a deodorant, containing the flavor or fragrance composition according to  claim 12 .