Organic Compounds having Taste-Modifying Properties

Abstract

This disclosure relates to flavour modification and to compounds of formula (I) or edible salts thereof, wherein R 1 is selected from C 6 -C 20 alkyl, and C 9 -C 25 alkenyl, and i) R 3 and R 4 are hydrogen and R 2 the residue of a proteinogenic amino acid; ii) R 2 and R 3 are methyl and R 4 is hydrogen; or R 4 is hydrogen and R 2 and R 3 form together with the carbon atom to which they are attached cyclopropyl; iii) R 2 is hydrogen, and R 3 and R 4 together are —CH 2 —CH 2 —CH 2 — useful in modifying flavours.

1 . A flavour composition comprising a flavour co-ingredient and a compound of formula (I) and/or edible salt thereof, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from C 6 -C 20  alkyl, and C 9 -C 25  alkenyl, and
 i) R 3  and R 4  are hydrogen and R 2  the residue of a proteinogenic amino acid; 
 ii) R 2  and R 3  are methyl and R 4  is hydrogen; or R 4  is hydrogen and R 2  and R 3  form together with the carbon atom to which they are attached cyclopropyl; 
 iii) R 2  is hydrogen, and R 3  and R 4  together are —CH 2 —CH 2 —CH 2 —. 
 
       
     
     
         2 . A flavour composition according to  claim 1  wherein the flavour co-ingredient is selected from: sugars, fats, salts, monosodium glutamate, calcium ions, phosphate ions, organic acids, proteins, purines, flavours, and mixtures thereof. 
     
     
         3 . A comestible product comprising a compound of formula (I) and/or an edible salt thereof, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from C 6 -C 20  alkyl, and C 9 -C 25  alkenyl, and
 i) R 3  and R 4  are hydrogen and R 2  the residue of a proteinogenic amino acid; 
 ii) R 2  and R 3  are methyl and R 4  is hydrogen; or R 4  is hydrogen and R 2  and R 3  form together with the carbon atom to which they are attached cyclopropyl; 
 iii) R 2  is hydrogen, and R 3  and R 4  together are —CH 2 —CH 2 —CH 2 —. 
 
       
     
     
         4 . A compound of formula (I) and/or edible salt thereof, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from C 6 -C 20  alkyl, and C 9 -C 25  alkenyl, and
 i) R 3  and R 4  are hydrogen and R 2  the residue of a proteinogenic amino acid; 
 ii) R 2  and R 3  are methyl and R 4  is hydrogen; or R 4  is hydrogen and R 2  and R 3  form together with the carbon atom to which they are attached cyclopropyl; 
 iii) R 2  is hydrogen, and R 3  and R 4  together are —CH 2 —CH 2 —CH 2 —. 
 
       
     
     
         5 . A method of modifying the taste of comestible composition comprising at least one flavour co-ingredient comprising adding to said composition a compound of formula (I) and/or an edible salt thereof, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from C 6 -C 20  alkyl, and C 9 -C 25  alkenyl, and
 i) R 3  and R 4  are hydrogen and R 2  the residue of a proteinogenic amino acid; 
 ii) R 2  and R 3  are methyl and R 4  is hydrogen; or R 4  is hydrogen and R 2  and R 3  form together with the carbon atom to which they are attached cyclopropyl; 
 iii) R 2  is hydrogen, and R 3  and R 4  together are —CH 2 —CH 2 —CH 2 —. 
 
       
     
     
         6 . A taste-modifying agent adapted for use in a consumable product, the taste-modifying agent comprising a compound of formula (I) and/or an edible salt thereof, 
       
         
           
           
               
               
           
         
         wherein 
         R 1  is selected from C 6 -C 20  alkyl, and C 9 -C 25  alkenyl, and
 i) R 3  and R 4  are hydrogen and R 2  the residue of a proteinogenic amino acid; 
 ii) R 2  and R 3  are methyl and R 4  is hydrogen; or R 4  is hydrogen and R 2  and R 3  form together with the carbon atom to which they are attached cyclopropyl; 
 iii) R 2  is hydrogen, and R 3  and R 4  together are —CH 2 —CH 2 —CH 2 —. 
 
       
     
     
         7 . A flavour composition according to  claim 1 , wherein the compound of formula (I) is selected from:
 2-amino-4-(methylthio)-N-octadecylbutanamide;   2-amino-4-methyl-N-octadecylpentanamide;   N-octadecylpyrrolidine-2-carboxamide;   4-amino-N-octadecylbutanamide; 1-amino-N-octadecylcyclopropanecarboxamide;   (Z)-4-amino-N-(octadec-9-en-1-yl)butanamide; and,   N-hexadecyl 4-aminobutyramide.   
     
     
         8 . A comestible product according to  claim 3 , wherein the compound of formula (I) is selected from:
 2-amino-4-(methylthio)-N-octadecylbutanamide;   2-amino-4-methyl-N-octadecylpentanamide;   N-octadecylpyrrolidine-2-carboxamide;   4-amino-N-octadecylbutanamide; 1-amino-N-octadecylcyclopropanecarboxamide;   (Z)-4-amino-N-(octadec-9-en-1-yl)butanamide; and,   N-hexadecyl 4-aminobutyramide.   
     
     
         9 . A compound according to  claim 4 , wherein the compound of formula (I) is selected from:
 2-amino-4-(methylthio)-N-octadecylbutanamide;   2-amino-4-methyl-N-octadecylpentanamide;   N-octadecylpyrrolidine-2-carboxamide;   4-amino-N-octadecylbutanamide; 1-amino-N-octadecylcyclopropanecarboxamide;   (Z)-4-amino-N-(octadec-9-en-1-yl)butanamide; and,   N-hexadecyl 4-aminobutyramide.   
     
     
         10 . A method according to  claim 5 , wherein the compound of formula (I) is selected from:
 2-amino-4-(methylthio)-N-octadecylbutanamide;   2-amino-4-methyl-N-octadecylpentanamide;   N-octadecylpyrrolidine-2-carboxamide;   4-amino-N-octadecylbutanamide; 1-amino-N-octadecylcyclopropanecarboxamide;   (Z)-4-amino-N-(octadec-9-en-1-yl)butanamide; and,   N-hexadecyl 4-aminobutyramide.   
     
     
         11 . A taste-modifying agent according to to  claim 6 , wherein the compound of formula (I) is selected from:
 2-amino-4-(methylthio)-N-octadecylbutanamide;   2-amino-4-methyl-N-octadecylpentanamide;   N-octadecylpyrrolidine-2-carboxamide;   4-amino-N-octadecylbutanamide; 1-amino-N-octadecylcyclopropanecarboxamide;   (Z)-4-amino-N-(octadec-9-en-1-yl)butanamide; and,   N-hexadecyl 4-aminobutyramide.