Amide compounds and their use as flavor modifiers

A flavor-modifying compound, which is a compound selected from the group consisting of:

• ethyl (3,4-dimethylbenzoyl)-L-valinate;
• methyl (3,4-dimethylbenzoyl)-L-phenylalaninate;
• diethyl cinnamoyl-L-glutamate;
• ethyl (E)-(3-(4-methoxyphenyl)acryloyl)-L-valinate;
• methyl (E)-(3-(4-methoxyphenyl)acryloyl)-L-leucinate;
• ethyl (E)-(3-(4-ethoxyphenyl)acryloyl)-L-valinate;
• and
• ethyl (E)-(4-methylpent-2-enoyl)-L-leucinate;
• or a comestibly acceptable salt thereof.

A method of enhancing a salty taste, an umami taste, or a kokumi taste of an ingestible composition, the method comprising introducing to the ingestible composition a flavor-modifying compound, which is a compound of formula (I):

• or a comestibly acceptable salt thereof;
• wherein:
• R1 is C1-10 alkyl, C5-12cycloalkenyl, C6-14 aryl or C4-12 heteroaryl, wherein the alkyl group is optionally substituted one or more times by substituents selected independently from the group consisting of RX, and wherein the cycloalkyl, aryl, and heteroaryl groups are each optionally substituted one or more times by substituents selected independently from the group consisting of RY;
• R2 is C1-10 alkyl, —(C1-6 alkylene)-C6-14 aryl, or —(C1-6 alkylene)-C4-12 heteroaryl, wherein the alkyl group and alkylene moiety are each optionally substituted one or more times by substituents selected independently from the group consisting of RX, and wherein the aryl and heteroaryl moieties are each optionally substituted one or more times by substituents selected independently from the group consisting of RY;
• R3 is C1-10 alkyl, which is optionally substituted one or more times by substituents selected independently from the group consisting of RX;
• RX is a halogen atom, oxo, —CN, nitro, —OH, —NH2, —C(O)H, —O—C(O)H, —C(O)—OH, —NH—C(O)H, —C(O)—NH2, —O—(C1-6 alkyl), —NH—(C1-6 alkyl), —N(C1-6 alkyl)2, —C(O)—(C1-6 alkyl), —O—C(O)—(C1-6 alkyl), —NH—C(O)—(C1-6 alkyl), —C(O)—O—(C1-6 alkyl), —C(O)—NH—(C1-6 alkyl), —C(O)—N(C1-6 alkyl)2, —S(O)2—(C1-6 alkyl), —O—S(O)2—(C1-6 alkyl), —NH—S(O)2—(C1-6 alkyl), —S(O)2—O—(C1-6 alkyl), —S(O)2—NH—(C1-6 alkyl), —S(O)2—N(C1-6 alkyl)2, C3-10 cycloalkyl, C2-14 heterocyclyl, C6-14 aryl, C2-14 heteroaryl, C1-6 haloalkoxy, and C2-6 haloalkenyloxy;
• RY is a halogen atom, oxo, —CN, nitro, —OH, —NH2, —C(O)H, —O—C(O)H, —C(O)—OH, —NH—C(O)H, —C(O)—NH2, —O—(C1-6 alkyl), —NH—(C1-6 alkyl), —N(C1-6 alkyl)2, —C(O)—(C1-6 alkyl), —O—C(O)—(C1-6 alkyl), —NH—C(O)—(C1-6 alkyl), —C(O)—O—(C1-6 alkyl), —C(O)—NH—(C1-6 alkyl), —C(O)—N(C1-6 alkyl)2, —S(O)2—(C1-6 alkyl), —O—S(O)2—(C1-6 alkyl), —NH—S(O)2—(C1-6 alkyl), —S(O)2—O—(C1-6 alkyl), —S(O)2—NH—(C1-6 alkyl), —S(O)2—N(C1-6 alkyl)2, C3-10 cycloalkyl, C2-14 heterocyclyl, C6-14 aryl, C2-14 heteroaryl, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C2-6 haloalkenyl, C1-6 haloalkoxy, C2-6 haloalkenyloxy, (C1-6 alkoxy)-C1-6 alkyl, C1-6 alkyl, and C2-6 alkenyl, wherein any adjacent substituents on an aryl or heteroaryl ring can optionally combine to form a fused carbocyclic or heterocyclic ring having from 5 to 7 members;
• and
• n is 0, 1, or 2.

An ingestible composition comprising and a salty tastant, an umami tastant, a kokumi tastant, or any combination thereof, and a flavor-modifying compound, which is a compound of formula (I):

• or a comestibly acceptable salt thereof;
• wherein:
• R1 is C1-10 alkyl, C5-12 cycloalkenyl, C6-14 aryl or C4-12 heteroaryl, wherein the alkyl group is optionally substituted one or more times by substituents selected independently from the group consisting of RX, and wherein the cycloalkyl, aryl, and heteroaryl groups are each optionally substituted one or more times by substituents selected independently from the group consisting of RY;
• R2 is C1-10 alkyl, —(C1-6 alkylene)-C6-14 aryl, or —(C1-6 alkylene)-C4-12 heteroaryl, wherein the alkyl group and alkylene moiety are each optionally substituted one or more times by substituents selected independently from the group consisting of RX, and wherein the aryl and heteroaryl moieties are each optionally substituted one or more times by substituents selected independently from the group consisting of RY;
• R3 is C1-10 alkyl, which is optionally substituted one or more times by substituents selected independently from the group consisting of RX;
• RX is a halogen atom, oxo, —CN, nitro, —OH, —NH2, —C(O)H, —O—C(O)H, —C(O)—OH, —NH—C(O)H, —C(O)—NH2, —O—(C1-6 alkyl), —NH—(C1-6 alkyl), —N(C1-6 alkyl)2, —C(O)—(C1-6 alkyl), —O—C(O)—(C1-6 alkyl), —NH—C(O)—(C1-6 alkyl), —C(O)—O—(C1-6 alkyl), —C(O)—NH—(C1-6 alkyl), —C(O)—N(C1-6 alkyl)2, —S(O)2—(C1-6 alkyl), —O—S(O)2—(C1-6 alkyl), —NH—S(O)2—(C1-6 alkyl), —S(O)2—O—(C1-6 alkyl), —S(O)2—NH—(C1-6 alkyl), —S(O)2—N(C1-6 alkyl)2, C3-10 cycloalkyl, C2-14 heterocyclyl, C6-14 aryl, C2-14 heteroaryl, C1-6 haloalkoxy, and C2-6 haloalkenyloxy;
• RY is a halogen atom, oxo, —CN, nitro, —OH, —NH2, —C(O)H, —O—C(O)H, —C(O)—OH, —NH—C(O)H, —C(O)—NH2, —O—(C1-6 alkyl), —NH—(C1-6 alkyl), —N(C1-6 alkyl)2, —C(O)—(C1-6 alkyl), —O—C(O)—(C1-6 alkyl), —NH—C(O)—(C1-6 alkyl), —C(O)—O—(C1-6 alkyl), —C(O)—NH—(C1-6 alkyl), —C(O)—N(C1-6 alkyl)2, —S(O)2—(C1-6 alkyl), —O—S(O)2—(C1-6 alkyl), —NH—S(O)2—(C1-6 alkyl), —S(O)2—O—(C1-6 alkyl), —S(O)2—NH—(C1-6 alkyl), —S(O)2—N(C1-6 alkyl)2, C3-10 cycloalkyl, C2-14 heterocyclyl, C6-14 aryl, C2-14 heteroaryl, C1-6 alkyl, C2-6 alkenyl, C1-6 haloalkyl, C2-6 haloalkenyl, C1-6 haloalkoxy, C2-6 haloalkenyloxy, (C1-6 alkoxy)-C1-6 alkyl, C1-6 alkyl, and C2-6 alkenyl, wherein any adjacent substituents on an aryl or heteroaryl ring can optionally combine to form a fused carbocyclic or heterocyclic ring having from 5 to 7 members;
• and
• n is 0, 1, or 2.