Flavour Modulating Derivative of a Carboxylic Acid and a Purine, Pyrimidine, Nucleoside, or Nucleotide

Abstract

The present invention relates to the field of improving the flavour of foodstuffs, beverages, tobacco products, pharmaceutics and oral care products. More particularly, the present invention provides flavour modulating substances selected from the group represented by formula (I): and edible salts thereof and edible esters thereof, which can advantageously be used for modulating the flavour of foodstuffs, beverages, tobacco products, pharmaceutics and oral care products. These flavour modulating substances can be used to impart desirable taste attributes in a wide variety of applications and products. In addition, the present flavour modulating substances are capable of modulating the taste and/or aroma impact of other, flavour imparting, substances contained within these same products, thereby improving the overall flavour quality of these products.

1 . Flavour modulating substances according to formula (I) as well as edible salts and esters thereof: 
       
         
           
           
               
               
           
         
       
       wherein X represents
 hydrogen; 
 branched or unbranched, aliphatic or cyclic C 1 -C 12  alkyl or C 2 -C 12  alkenyl, each optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, thiol, lower thioalkyl, lower alkoxyl, guanidine and saturated or unsaturated heterocyclic moieties; 
 a moiety represented by the formula —Z-Phe, wherein Z represents a covalent bond or a branched or unbranched saturated or unsaturated C 1 -C 6  alkylene optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, and lower alkoxyl and wherein Phe represents phenyl, optionally substituted with one or more substituents selected from hydroxyl, amine and lower alkoxyl; 
 a moiety represented by the formula —Y-CO-NHR, wherein Y represents branched or unbranched saturated or unsaturated C 1 -C 12  alkylene, optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, thiol, lower thioalkyl, lower alkoxyl and lower carboxyl;
 with the proviso that X does not represent a moiety wherein the a carbon atom is substituted with a hydroxyl group; 
 and wherein R represents (i) a moiety comprising a six membered heterocyclic ring, comprising at least two nitrogen atoms, which heterocyclic ring is optionally further substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; 
 
 alkyl; ribose; deoxyribose; phosphate esters of ribose; and phosphate esters of deoxyribose; or (ii) a moiety comprising a bicyclic fused ring system comprising a five membered heterocyclic ring and a six membered heterocyclic ring, each ring comprising at least two nitrogen atoms, and each ring being optionally further substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; ribose; deoxyribose; phosphate esters of ribose; and phosphate esters of deoxyribose. 
 
     
     
         2 . Flavour modulating substance according to  claim 1 , wherein the moiety —NRH represents the residue of a purine radical, a pyrimidine radical, a nucleoside or a nucleotide. 
     
     
         3 . Flavour modulating substance according to  claim 1 , wherein the moiety —NRH represents the residue of cytosine, guanine, adenine, guanosine, adenosine, cytidine, or cytidine 5′- monophosphate (CMP). 
     
     
         4 . Flavour modulating substance according to  claim 1 , wherein X represents, hydrogen;
 branched or unbranched C 1 -C 8  alkyl optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, thiol, lower thioalkyl, lower alkoxyl, guanidine, imidazole, indole and pyrrolidine; saturated or unsaturated C 2 -C 8  carboxyl, optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine and lower carboxyl; a moiety represented by the formula —Z-Phe, wherein Z represents a covalent bond or a saturated or unsaturated C 1 -C 4  alkylene, optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, and lower alkoxyl; or a moiety represented by the formula —Y-CO-NHR, wherein Y represents saturated or unsaturated C 1 -C 8  alkylene, optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine and lower carboxyl.   
     
     
         5 . Flavour modulating substance according to  claim 1 , wherein X represents branched or unbranched C 1 -C 4  alkyl, optionally wherein X represents C 1 -C 2  alkyl. 
     
     
         6 . Flavour modulating substance according to  claim 1 , wherein X is chosen such that the moiety X-CO- represents the residue of a carboxylic acid selected from the group of formic acid, propionic acid, butyric acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, oxalic acid, succinic acid, glutaric acid, fumaric acid, maleic acid, adipic acid, citric acid, pyruvic acid, oxalacetic acid, cinnamic acid, caffeic acid, benzoic acid, gallic acid, vanillic acid, anthranilic acid, glycine, alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine and valine. 
     
     
         7 . Flavour modulating substance selected from the group of N-formyl GMP, N-propanoyl GMP, N-butanoyl GMP, N-pentanoyl GMP, N-hexanoyl GMP, N-heptanoyl GMP, N-octanoyl GMP, N-oxalyl GMP, N-succinyl GMP, N-glutaryl GMP, N-fumaryl GMP, N-maleyl GMP, N-adipyl GMP, N-citryl GMP, N-galloyl GMP, N-oxalacetyl-GMP, N-feruloyl GMP, N-pyruvyl GMP, N-benzoyl GMP, N-vanilloyl GMP, N-anthranoyl GMP, N-caffeoyl GMP, N-cinnamoyl GMP, edible salts thereof and edible esters thereof 
     
     
         8 . Flavouring compositions comprising at least 60 ppt of one or more flavour modulating substances as defined in  claim 7 , as well as at least 0.1 wt % of one or more flavouring substances. 
     
     
         9 . Product selected from the group of foodstuffs, beverages, pharmaceutics, oral care products and tobacco products, said product comprising a flavour modulating amount of one or more flavour modulating substances as defined in  claim 1 . 
     
     
         10 . Product according to  claim 9 , wherein said flavour modulating amount is an amount of at least 0.3 ppt. 
     
     
         11 . Method of improving the flavour of a product selected from the group of foodstuffs, beverages, pharmaceutics, oral care products and tobacco products, said method comprising incorporating in said product a flavour modulating amount of one or more flavour modulating substances as defined in  claim 1 . 
     
     
         12 . Method according to  claim 11 , wherein said flavour modulating amount is an amount of at least 0.3 ppt. 
     
     
         13 . Process of producing a process flavour preparation comprising heating a mixture of
 a. (i) a carbohydrate source;   b. (ii) a nitrogen source, said nitrogen source comprising 0.5-100 wt %, of one or more amines represented by the formula NH 2 R, wherein R represents (a) a moiety comprising a six membered heterocyclic ring, comprising at least two nitrogen atoms, which heterocyclic ring is optionally further substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; ribose; deoxyribose; phosphate esters of ribose; and phosphate esters of deoxyribose; or (b) a moiety comprising a bicyclic fused ring system comprising a five membered heterocyclic ring and a six membered heterocyclic ring, each ring comprising at least two nitrogen atoms, and each ring being optionally further substituted with one or more substituents selected from the group of amino; hydroxyl; oxo; alkyl; ribose; deoxyribose; phosphate esters of ribose; and phosphate esters of deoxyribose; and   c. (iii) one or more of carboxylic acids represented by formula (II) and/or salts thereof:   
       
         
           
           
               
               
           
         
       
       wherein X represents
 hydrogen; 
 branched or unbranched, aliphatic or cyclic C 1 -C 12  alkyl or C 2 -C 12  alkenyl, each optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, thiol, lower thioalkyl, lower alkoxyl, guanidine and saturated or unsaturated heterocyclic moieties; 
 a moiety represented by the formula —Z-Phe, wherein Z represents a covalent bond or a branched or unbranched saturated or unsaturated C 1 -C 6  alkylene optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, and lower alkoxyl and wherein Phe represents phenyl, optionally substituted with one or more substituents selected from hydroxyl, amine and lower alkoxyl; 
 a moiety represented by the formula —Y-CO-NHR, wherein Y represents branched or unbranched saturated or unsaturated C 1 -C 12  alkylene, optionally substituted with one or more substituents selected from the group of oxo, hydroxyl, amine, thiol, lower thioalkyl, lower alkoxyl and lower carboxyl; 
 
       with the proviso that X does not represent a moiety wherein the a carbon atom is substituted with a hydroxyl group. 
     
     
         14 . Process according to  claim 13 , wherein the nitrogen source comprises 0.5-100 wt % of GMP. 
     
     
         15 . Flavouring compositions comprising at least 60 ppt of one or more flavour modulating substances as defined in  claim 1 , as well as at least 0.1 wt % of one or more flavouring substances. 
     
     
         16 . Product selected from the group of foodstuffs, beverages, pharmaceutics, oral care products and tobacco products, said product comprising a flavour modulating amount of one or more flavour modulating substances as defined in  claim 7 . 
     
     
         17 . Product according to  claim 16 , wherein said flavour modulating amount is an amount of at least 0.3 ppt. 
     
     
         18 . Method of improving the flavour of a product selected from the group of foodstuffs, beverages, pharmaceutics, oral care products and tobacco products, said method comprising incorporating in said product a flavour modulating amount of one or more flavour modulating substances as defined in  claim 7 . 
     
     
         19 . Method according to  claim 18 , wherein said flavour modulating amount is an amount of at least 0.3 ppt. 
     
     
         20 . Flavour modulating substance selected from the group of N-formyl AMP, N-propanoyl AMP, N-butanoyl AMP, N-pentanoyl AMP, N-hexanoyl AMP, N-heptanoyl AMP, N-octanoyl AMP, N-oxalyl AMP, N-succinyl AMP, N-glutaryl AMP, N-fumaryl AMP, N-maleyl AMP, N-adipyl AMP, N-citryl AMP, N-galloyl AMP, N-oxalacetyl-AMP, N-feruloyl AMP, N-pyruvyl AMP, N-benzoyl AMP, N-vanilloyl AMP, N-anthranoyl AMP, N-caffeoyl AMP, N-cinnamoyl AMP, N-acetyl CMP, N-formyl CMP, N-propanoyl CMP, N-butanoyl CMP, N-pentanoyl CMP, N-hexanoyl CMP, N-heptanoyl CMP, N-octanoyl CMP, N-oxalyl CMP, N-succinyl CMP, N-glutaryl CMP, N-fumaryl CMP, N-maleyl CMP, N-adipyl CMP, N-citryl CMP, N-galloyl CMP, N-oxalacetyl-CMP, N-feruloyl CMP, N-pyruvyl CMP, N-benzoyl CMP, N-vanilloyl CMP, N-anthranoyl CMP, N-caffeoyl CMP, N-cinnamoyl CMP, edible salts thereof and edible esters thereof.