Pyridine Derivatives With Umami Flavour

Abstract

A compound (including salts thereof) according to Formula I in which R 1 is H, methyl or ethyl; R 2 is H, OH, fluorine, C 1 -C 4 linear or branched alkyl, C 1 -C 6 alkoxy wherein the alkyl group is linear or branched, or a C 3 -C 5 cycloalkyl moiety; R 3 is H, methoxy, methyl or ethyl; or R 2 and R 3 together form a bridging moiety —O—CH 2 —O— between the phenyl carbon atoms to which they are connected; R 4 is OH or methoxy; and R 5 and R 6 are independently H or methyl; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are such that, (i) when R 2 and R 3 together form a bridging moiety —O—CH 2 —O— between the phenyl carbon atoms to which they are connected, R 1 , R 5 , R 6 are H, and R 4 is OH; and (ii) when R 4 is OH and R 1 -R 3 are H, at least one of R 5 , R 6 is methyl, which compound or salt thereof provides umami flavour.

1 . A umami flavouring compound according to Formula I or salt thereof 
       
         
           
           
               
               
           
         
         in which 
         R 1  comprises H, methyl or ethyl; 
         R 2  comprises H, OH, fluorine, C 1 -C 4  linear or branched alkyl, C 1 -C 6  alkoxy 
         wherein the alkyl group is linear or branched, or a C 3 -C 5  cycloalkyl moiety; 
         R 3  comprises H, methoxy, methyl or ethyl; 
         or R 2  and R 3  together form a bridging moiety —O—CH 2 —O— between the phenyl carbon atoms to which they are connected; 
         R 4  comprises OH or methoxy; and 
         R 5  and R 6  independently comprise H or methyl; 
         R 1 , R 2 , R 3 , R 4 , R 5  and R 6  are such that, 
         (i) when R 2  and R 3  together form a bridging moiety —O—CH 2 —O— between the phenyl carbon atoms to which they are connected, R 1 , R 5 , R 6  are H, and R 4  is OH; and 
         (ii) when R 4  is OH and R 1 -R 3  are H, at least one of R 5  or R 6  is methyl, which compound or salt thereof provides umami flavouring. 
       
     
     
         2 . The umami flavouring compound according to  claim 1 , in which R 3  is selected from H and methoxy. 
     
     
         3 . The umami flavouring compound according to  claim 1 , in which R 2  comprises H, OH, fluorine, methyl, C 1 -C 6  alkoxy wherein the alkyl group is linear or branched, or a C 3 -C 5  cycloalkyl moiety. 
     
     
         4 . The umami flavouring compound according to  claim 1 , in which R 2  consists of a C 3 -C 5  cycloalkyl moiety. 
     
     
         5 . The umami flavouring compound according to  claim 1 , in which R 1  comprises H or methyl, R 2  comprises methyl, methoxy or isobutyloxy, R 3  is H, R 4  is OH, and R 5  and R 6  are H. 
     
     
         6 . The umami flavouring compound according to  claim 5 , selected from the group consisting of:
 1-(2-hydroxy-4,5-dimethylphenyl)-3-(pyridine-2-yl)propan-1-one;   1-(2-hydroxy-4-methylphenyl)-3-(pyridin-2-yl)propan-1-one;   1-(2-hydroxy-4-methoxyphenyl)-3-(pyridin-2-yl)propan-1-one;   1-(2-hydroxy-4-isobutoxyphenyl)-3-(pyridine-2-yl)propan-1-one;   and mixtures thereof.   
     
     
         7 . A method of providing umami flavour to a consumable composition, comprising the addition to the composition of at least one umami flavouring compound according to  claim 1 , which compound provides umami flavour. 
     
     
         8 . A consumable composition having an umami flavour, comprising a product base and at least one umami flavouring compound according to  claim 1 , which compound provides umami flavour. 
     
     
         9 . The consumable composition according to  claim 8 , in which the umami flavouring compound is present at a concentration of from about 0.01 to about 100 ppm. 
     
     
         10 . The consumable composition according to  claim 8 , in which the umami flavouring compound is present at a concentration of from about 0.1 to about 50 ppm. 
     
     
         11 . The consumable composition according to  claim 8 , in which the umami flavouring compound is present at a concentration of from about 0.2 to about 10 ppm.