Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions

A N-substituted unsaturated alkyl amide compound having the structure selected from the group consisting of structure 3 and structure 4:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• or if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of C1-C4 alkyl, alkenyl;
• removed methylene
• R5 is selected from the group consisting of H, methyl or ethyl;
• R6 is selected from the group consisting of H, methyl and ethyl;
• R7 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• except for in the case of structure 3 when if R5=H or methyl and R6=H or methyl, R7 as described above and phenyl.

A method of enhancing the salty taste of salt-containing beverages, foodstuff, chewing gum, dental and oral hygiene products which comprises adding a salt enhancing level of the structure selected from the group consisting of structure 3 and structure 4:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• or if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of C1-C4 alkyl, alkenyl;
• removed methylene
• R5 is selected from the group consisting of H, methyl or ethyl;
• R6 is selected from the group consisting of H, methyl and ethyl;
• R7 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• except for in the case of structure 3 when if R5=H or methyl and R6=H or methyl, R7 as described above and phenyl.

A N-substituted unsaturated alkyl amide compound having the structure:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• or if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of C1-C4 alkyl;
• R5 is selected from the group consisting of H, methyl or ethyl;
• R6 is selected from the group consisting of H, methyl and ethyl;
• R7 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• except for in the case of structure 4 when if R5=H or methyl and R6=H or methyl, R7 as described above and phenyl.

A method of enhancing the salty taste of salt-containing beverages, foodstuff, chewing gum, dental and oral hygiene products which comprises adding a salt enhancing level of the structure:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• or if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of C1-C4 alkyl;
• R5 is selected from the group consisting of H, methyl or ethyl;
• R6 is selected from the group consisting of H, methyl and ethyl;
• R7 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• except for in the case of structure 4 when if R5=H or methyl and R6=H or methyl, R7 as described above and phenyl.

A foodstuff or beverage containing wherein the salt or umami taste enhancer (a) is selected from the group consisting of:

• 2-butenamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-, (2E)-2-butenamide, N-[(2Z)-3,7-dimethyl-2,6-octadienyl]-, (2E)-2-butenamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-3-methyl-2-butenamide, N-[(2Z)-3,7-dimethyl-2,6-octadienyl]-3-methyl-2-butenamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-2-methyl-(2E)-2-butenamide, N-[(2Z)-3,7-dimethyl-2,6-octadienyl]-2-methyl-(2E)-Cyclopropanecarboxamide, N-[(2Z,6Z)-2,6-nonadienyl]-Cyclopropanecarboxamide, N-[(2E,6Z)-2,6-nonadienyl]-Cyclopropanecarboxamide, N-[(2E)-3-(3-cyclohexen-1-yl)-2-propenyl]-Cyclopropanecarboxamide, N-[(2E,6Z)-2,6-dodecadienyl]-Cyclopropanecarboxamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-Cyclopropanecarboxamide, N-[(2Z)-3,7-dimethyl-2,6-octadienyl]-Propanamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-2-methyl-Propanamide, N-[(2Z)-3,7-dimethyl-2,6-octadienyl]-2-methyl-Acetamide, N-[(2Z,6Z)-2,6-nonadienyl]-Acetamide, N-[(2E,6Z)-2,6-nonadienyl]-Acetamide, N-[(2Z,6Z)-2-methyl-2,6-nonadienyl]-Acetamide, N-[(2Z,6Z)-2-methyl-2,6-nonadienyl]-Cyclopropanecarboxamide, N-[[2-methyl-2-(4-methyl-3-pentenyl)cyclopropyl]methyl]-Acetamide, N-[[2-methyl-2-(4-methyl-3-pentenyl)cyclopropyl]methyl]-Cyclopropanecarboxamide, N-methyl-N-[(2E,6Z)-2,6-nonadienyl]-Cyclopropanecarboxamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-N-methyl- Cyclopropanecarboxamide, N-[(2E)-3,7-dimethyl-2,6-octadienyl]-N-ethyl-Propanamide, N-[(2E,6Z)-2,6-nonadienyl]-N-cyclopropylmethyl-N,N,3,7-Tetramethylocta-2,6-dienamide,(2E)-2-propenamide, 3-(3-cyclohexen-1-yl)-N-ethyl-,(2E)-3,7-dimethyl-2,6-octadienamide, N-ethyl-,(2E)-2,6-nonadienamide, N,N-dimethyl-, (2E,6Z)-2,6-nonadienamide, N-cyclopropyl, 2-methyl-, (2E,6Z)—-2,6-dodecadienamide, N-ethyl-, (2E,6Z)-2,6-nonadienamide, N-cyclopropyl-, (2E,6Z)-2,6-nonadienamide, N-ethyl-, (2E,6Z)-.

A N-substituted unsaturated alkyl amide compound having the structure selected from the group consisting of structure 1 and structure 2:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• or if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of H, methyl or ethyl;
• R5 is selected from the group consisting of H, methyl and ethyl;
• R6 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• with the proviso that in structure 1 when R4 is H or methyl;
• and R5 is H or methyl, R6 may be selected from the group described above phenyl, and if R1=H and R2=H, then R3 can not be H or methyl unless R4=R5=H.

The compound of the formula

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• or if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of H, methyl or ethyl;
• R5 is selected from the group consisting of H, methyl and ethyl;
• R6 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• with the proviso that in structure 1 when if R4 is H or methyl and R5 is H or methyl, R6 may be selected from the group described above and phenyl, and if R1=H and R2=H, then R3 can not be H or methyl unless R4=R5=H.

A method of enhancing the salty taste of salt-containing beverages, foodstuff, chewing gum, dental and oral hygiene products which comprises adding a salt enhancing level of the structure selected from the group consisting of structure 1 and structure 2:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of H, methyl or ethyl;
• R5 is selected from the group consisting of H, methyl and ethyl;
• R6 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• with the proviso that in structure 1 when if R4 is H or methyl and R5=H or methyl, R6 may be selected from the group described above and phenyl, and if R1=H and R2=H, then R3 can not be H or methyl unless R4=R5=H.

In combination an organoleptically acceptable amount of the compound having the structure selected from the group consisting of structure 1 and structure 2:

• where R1=H or methyl;
• R2 is selected from the group consisting of H, C1-C4 alkyl, alkenyl and methylene;
• R3 is selected from the group consisting of H, C1-C8 straight or branched chain alkyl, alkenyl, dienalkyl and phenyl;
• if R1=H, R2 and R3 taken together can represent
• cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl;
• or if R1=Me, R2 and R3 taken together can represent
• or cyclopropyl,
• R4 is selected from the group consisting of H, methyl or ethyl;
• R5 is selected from the group consisting of H, methyl and ethyl;
• R6 is selected from the group consisting of H, C1-C9 straight or branched chain alkyl, alkenyl, alkyldienyl, acyclic or containing no more than one ring;
• with the proviso that in structure 1 when if R4 is H or methyl and R5=H or methyl, R6 may be selected from the group described above and phenyl, and if R1=H and R2=H, then R3 can not be H or methyl unless R4=R5=H.