Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof

Abstract

The present invention relates to the discovery that certain non-naturally occurring, non-peptide amide compounds and amide derivatives, such as oxalamides, ureas, and acrylamides, are useful flavor or taste modifiers, such as a flavoring or flavoring agents and flavor or taste enhancer, more particularly, savory (the “umami” taste of monosodium glutamate) or sweet taste modifiers, —savory or sweet flavoring agents and savory or sweet flavor enhancers, for food, beverages, and other comestible or orally administered medicinal products or compositions.

1 . A method for modulating the taste of a comestible or medicinal product comprising: a) providing at least one comestible or medicinal product, or a precursor thereof, and b) combining the comestible or medicinal product or precursor thereof with at least a savory flavor modulating amount of at least one non-naturally occurring amide compound, or a comestibly acceptable salt thereof, so as to form a modified comestible or medicinal product; wherein the amide compound has the formula: 
       
         
           
           
               
               
           
         
         wherein R 1  comprises a hydrocarbon residue having at least three carbon atoms and optionally one to ten heteroatoms independently selected from oxygen, nitrogen, sulfur, halogens, or phosphorus; and wherein one of R 2  and R 3  is H the other of R 2  and R 3  comprises a hydrocarbon residue having at least three carbon atoms and optionally one to ten heteroatoms independently selected from oxygen, nitrogen, sulfur, halogens, or phosphorus; and wherein the amide compound has a molecular weight of 500 grams per mole or less. 
       
     
     
         2 . The method of  claim 1  wherein the amide compound has a molecular weight from 175 to 500 grams per mole. 
     
     
         3 . The method of  claim 1  wherein the amide compound has a molecular weight from 200 to 450 grams per mole. 
     
     
         4 . The method of  claim 1  wherein the amide compound has a molecular weight from 225 to 400 grams per mole. 
     
     
         5 . The method of  claim 1  wherein the amide compound has a molecular weight from 250 to 350 grams per mole. 
     
     
         6 . The method of  claim 1  wherein R 1  and one of R 2  and R 3  have between 3 and 14 carbon atoms. 
     
     
         7 . The method of  claim 2  wherein R 1  and one of R 2  and R 3  have between 4 and 12 carbon atoms. 
     
     
         8 . The method of  claim 1  wherein R 1  and one of R 2  and R 3  have between 4 and 10 carbon atoms. 
     
     
         9 . The method of  claim 1  wherein R 1  has between 3 and 16 carbon atoms and 0, 1, 2, 3, 4, or 5 heteroatoms selected from oxygen, nitrogen, sulfur, fluorine, or chlorine. 
     
     
         10 . The method of  claim 1  wherein one of R 2  or R 3  has between 3 and 16 carbon atoms and 0, 1, 2, 3, 4, or 5 heteroatoms independently selected from oxygen, nitrogen, sulfur, fluorine, or chlorine. 
     
     
         11 . The method of  claim 1  wherein one of R 2  or R 3  has between 4 and 14 carbon atoms and 0, 1, 2, 3, 4, or 5 heteroatoms independently selected from oxygen, nitrogen, sulfur. 
     
     
         12 . The method of  claim 1  wherein one of R 2  or R 3  has between 5 and 12 carbon atoms and 0, 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur. 
     
     
         13 . The method of  claim 1  wherein R 1  has between 3 and 16 carbon atoms and 0, 1, 2, 3, 4, or 5 heteroatoms selected from oxygen, nitrogen, sulfur, fluorine, or chlorine, and one of R 2  or R 3  has between 5 and 12 carbon atoms and 0, 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur. 
     
     
         14 . The method of  claim 1  wherein R 1  and one of R 2  and R 3  are independently selected from the group consisting of an arylalkenyl, heteroarylalkenyl, arylalkyl, heteroarylalkyl, alkyl, alkoxy-alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, —R 4 OH, —R 4 OR 5  —R 4 CN, —R 4 CO 2 H, —R 4 CO 2 R 5 , —R 4 COR 5 , —R 4 SR 5 , and —R 4 SO 2 R 5 , and optionally substituted derivative thereof comprising 1, 2, 3, or 4 carbonyl, amino groups, hydroxyl, or halogen groups: and wherein R 4  and R 5  are Q-Q hydrocarbon residues. 
     
     
         15 . The method of  claim 7  wherein R 1  and one of R 2  and R 3  are independently selected from the group consisting of an arylalkenyl, heteroarylalkenyl, arylalkyl, heteroarylalkyl, alkyl, alkoxy-alkyl, alkenyl, cycloalkyl, cycloalkenyl, heterocycle, aryl, and heteroaryl groups, and optionally substituted derivatives thereof comprising 1, 2, 3, or 4 substituent groups, independently selected from hydrogen, hydroxy, fluoro, chloro, NH 2 , NHCH 3 , N(CH 3 ) 2 , CO 2 CH 3 , SEt, SCH 3 , methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy groups. 
     
     
         16 . The method of  claim 1  wherein one of R 2  and R 3  is a branched or cyclic organic residue having a carbon atom directly bonded to (a) the amide nitrogen atom and (b) two additional carbon atoms, and wherein the branched or cyclic organic residue comprises hydrogen atoms, up to 10 optional additional carbon atoms, and from zero to five heteroatoms independently selected from oxygen, nitrogen, sulfur, fluorine, and chlorine. 
     
     
         17 . The method of  claim 1  wherein one of R and R has the formula 
       
         
           
           
               
               
           
         
         wherein na and nb are independently selected from 1, 2, and 3, and each R a  or R 2  substituent residue is independently selected from hydrogen, a halogen, a hydroxy, or an carbon-containing residue optionally having from zero to five heteroatoms independently selected from oxygen, nitrogen, sulfur, an a halogen. 
       
     
     
         18 . The method of  claim 1  wherein one of R and R is a branched alkyl radical having 1 five to 12 carbon atoms. 
     
     
         19 . The method of  claim 1  wherein one of R 2  and R 3  is a cycloalkyl or cycloalkenyl ring comprising 5 to 12 ring carbon atoms that can be optionally substituted with 1, 2, 3, or 4 independently selected from hydrogen, hydroxy, fluoro, chloro, NH 2 , NHCH 3 , N(CH 3 ) 2 , CO 2 CH 3 , SEt, SCH 3 , methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy groups. 
     
     
         20 . The method of  claim 1  wherein one of R and R has the structure 
       
         
           
           
               
               
           
         
         wherein Ar is a phenyl, pyridyl, furanyl, thiofuranyl, or pynole ring, m is 0, 1, 2, or 9*3, each R is independently selected from hydrogen, hydroxy, fluoro, chloro, NH 2 , NHCH 3 , N(CH 3 ) 2 , CO 2 CH 3 , SEt, SCH 3 , methyl, ethyl, isopropyl, vinyl, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy and R 2a  is selected from the group consisting of an alkyl, alkoxy-alkyl, alkenyl, cycloalkenyl, cycloalkyl, —R 4 OH, —R 4 O R 5 —R 4 CN, —R 4 CO 2 H, —R 4 CO 2 R 5 , —R 4 COR 5 , —R 4 SR 5 , and —R 4 SO R 5  comprising 1 to 12 carbon atoms. 
       
     
     
         21 - 322 . (canceled)