Aromatic neomenthylamides as flavoring substances

1. A method of imparting or intensifying an umami flavor comprising adding to a substance

(a) one or more compounds selected from the group consisting of compounds of Formulae (I) and (ent-I)

wherein in Formulae (I) and (ent-I) the following applies:

the aromatic radical Ar is selected from the group consisting of:

wherein the dotted line marks the bond linking the aromatic radical Ar to the adjacent carbonyl carbon atom in Formula (I) or (ent-I),

and wherein

R 1 and R 2 in the aromatic radicals A and B are selected independently of one another from the group consisting of H, OCH 3 , and COOCH 3 , or

R 1 and R 2 are adjacent and jointly form an OCH 2 O group, and

X in the aromatic radical C is O, and

(b) optionally, one or more compounds selected from the group consisting of Formulae (II), (ent-II), (III), (ent-III), (IV), and (ent-IV):

wherein Formulae (II), (ent-II), (III), (ent-III), (IV), and (ent-IV), have independently of one another one of the meanings specified for Formulae (I) and (ent-I),

wherein the ratio by weight of (a) all of the compounds of Formulae (I) and (ent-I) to (b) all of the compounds of Formulae (II), (ent-II), (III), (ent-III), (IV) and (ent-IV), if present, is at least 90:10, thereby imparting or intensifying an umami flavor.

2. The method according to claim 1 , wherein the

(a) one or more compounds are selected from the group consisting of compounds of Formulae (I) and (ent-I), wherein the aromatic radical Ar is selected from the group consisting of:

3. The method according to claim 1 , wherein the

(a) one or more compounds are selected from the group consisting of:

(1) N-((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)terephthalic acid methyl ester,

(2) N-((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)terephthalic acid methyl ester,

(3) benzo[1,3]dioxol-5-carboxylic acid ((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)amide,

(4) benzo[1,3]dioxol-5-carboxylic acid ((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)amide,

(5) 2-benzo[1,3]dioxol-5-yl-N-((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)acetamide, and

(6) 2-benzo[1,3]dioxol-5-yl-N-((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)acetamide

4. The method according to claim 1 comprising adding one or more pairs of enantiomers of compounds of Formula (I) and Formula (ent-I) to the substance.

5. The method according to claim 1 , wherein the one or more compounds are selected from the group consisting of benzo[1,3]dioxol-5-carboxylic acid ((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)amide and benzo[1,3]dioxol-5-carboxylic acid ((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)amide.

6. The method according to claim 1 further comprising adding to the substance,

(b) one or more compounds selected from the group consisting of Formulae (II), (ent-II), (III), (ent-III), (IV), and (ent-IV).

7. An individual compound or a mixture comprising

(a) two or more compounds selected from the group consisting of compounds of Formulae (I) and (ent-I)

wherein in Formulae (I) and (ent-I) the following applies:

the aromatic radical Ar is independently selected from the group consisting of:

wherein the dotted line marks the bond linking the aromatic radical Ar to the adjacent carbonyl carbon atom in Formula (I) or (ent-I), and

R 1 and R 2 in the aromatic radicals A and B are selected independently of one another from the group consisting of H, OCH 3 , and COOCH 3 , or

R 1 and R 2 are adjacent and jointly form an OCH 2 O group, and

X in the aromatic radical C is O, on the condition that

(i) individual compounds of Formula (I), in which the aromatic radical Ar is selected from the group consisting of

and

(ii) mixtures consisting of a pair of enantiomers of Formulae (I)/(ent-I) with an aromatic radical selected from the group consisting of

and

(iii) mixtures consisting of benzoyl-d-neomenthylamine and benzoyl-l-menthylamine or benzoyl-d-neomenthylamine and benzoyl-d-isomenthylamine are excluded and

(b) optionally one or more compounds selected from the group consisting of Formulae (II), (ent-II), (III), (ent-III), (IV), and (ent-IV):

wherein Formulae (II), (ent-II), (III), (ent-III), (IV), and (ent-IV) have, independently of one another, one of the meanings specified for Formulae (I) and (ent-I),

wherein the ratio by weight of (a) all of the compounds of Formulae (I) and (ent-I) to (b) all of the compounds of Formulae (II), (ent-II), (III), (ent-III), (IV) and (ent-IV), if present, is at least 90:10, and

wherein the compound or mixture imparts or intensifies an umami flavor.

8. The mixture according to claim 7 , wherein the aromatic radical Ar is independently selected from the group consisting of:

9. The individual compound or mixture according to claim 7 , wherein the compounds of Formulae (I) and (ent-I) are selected from the group consisting of:

(1) N-((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)terephthalic acid methyl ester

(2) N-((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)terephthalic acid methyl ester

(3) benzo[1,3]dioxol-5-carboxylic acid ((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)amide

(4) benzo[1,3]dioxol-5-carboxylic acid ((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)amide

(5) 2-benzo[1,3]dioxol-5-yl-N-((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)acetamide

(6) 2-benzo[1,3]dioxol-5-yl-N-((1R,2R,5S)-2-isopropyl-5-methyl cyclohexyl)acetamide

10. The mixture according to claim 7 , comprising one or more pairs of enantiomers each consisting of a compound of Formula (I) and a compound of Formula (ent-I).

11. The mixture according to claim 7 , wherein the two or more compounds selected from the group consisting of Formulae (I) and (ent-I) comprise the following compounds:

benzo[1,3]dioxol-5-carboxylic acid ((1S,2S,5R)-2-isopropyl-5-methylcyclohexyl)amide and

benzo[1,3]dioxol-5-carboxylic acid ((1R,2R,5S)-2-isopropyl-5-methylcyclohexyl)amide.

12. A mixture according to claim 7 comprising

one or more compounds selected from the group consisting of Formulae (II), (ent-II), (III), (ent-III), (IV), and (ent-IV).

13. A composition comprising a compound or a mixture according to claim 7 and one or more further constituents suitable for consumption, wherein the ratio by weight of the total mass of the compounds of Formulae (I) and (ent-I) or the total mass of the compounds of Formulae (I), (ent-I), (II), (ent-II), (III), (ent-III), (IV), and (ent-IV) to the further constituents suitable for consumption lies in the range of from 1:10 to 1:100,000, based on the dry mass of the composition.

14. The composition as claimed in claim 13 , wherein the further constituents suitable for consumption are:

solid excipients or

solid excipients and aroma compositions or

water, an oil phase, and one or more W/O emulsifiers, and,

optionally, one or more antioxidants, and,

optionally, one or more substances for intensifying an antioxidative effect.

15. The composition as claimed in claim 14 , wherein the further constituents suitable for consumption are solid excipients and the ratio by weight of the total mass of the compounds of Formulae (I) and (ent-I) or the total mass of the compounds of Formulae (I), (ent-I), (II), (ent-II), (III), (ent-III), (IV), (ent-IV) to the solid excipients lies in the range of from 1:10 to 1:100,000, based on the dry mass of the composition.

16. The composition as claimed in claim 14 , comprising

a total of from 0.01 to 0.1% by weight of one or more compounds of Formulae (I) and (ent-I), or of Formulae (I), (ent-I), (II), (ent-II), (III), (ent-III), (IV), (ent-IV),

5 to 30% by weight of water,

50 to 90% by weight of an oil phase,

0.1 to 5% by weight of an edible W/O emulsifier, based on the total mass of the composition, and, optionally, one or more antioxidants, and, optionally, one or more substances for intensifying an antioxidative effect.

17. A preparation comprising

a compound or mixture according to claim 7 , wherein the preparation has total of from 0.01 ppm to 100 ppm of one or more compounds of Formulae (I) and (ent-I) or of Formulae (I), (ent-I), (II), (ent-II), (III), (ent-III), (IV), and (ent-IV), based on the total weight of the preparation.

18. The preparation according to claim 17 , wherein the preparation is suitable for nutrition, oral care, or consumption for pleasure.

19. The preparation as claimed in claim 17 comprising

a total of from 10 ppm to 100,000 ppm of one or more compounds of Formulae (I) and (ent-I), or of Formulae (I), (ent-I), (II), (ent-II), (III), (ent-III), (IV), and (ent-IV)

no sodium glutamate or only from 0.00001 to 10% by weight, of sodium glutamate, and

optionally from 0.0001% by weight to 90% by weight, of an aroma composition, based on the total weight of the preparation.

20. The composition as claimed in claim 13 , additionally comprising a substance for masking or reducing an unpleasant flavor impression and/or a substance for intensifying the pleasant flavor impression of a pleasant-tasting substance.

21. The method of claim 1 , wherein the ratio by weight of (a) all of the compounds of Formulae (I) and (ent-I) to (b) all of the compounds of Formulae (II), (ent-II), (III), (ent-III), (IV) and (ent-IV), if present, is at least 95:5.

22. An individual compound or mixture of claim 7 , wherein the ratio by weight of (a) all of the compounds of Formulae (I) and (ent-I) to (b) all of the compounds of Formulae (II), (ent-II), (III), (ent-III), (IV) and (ent-IV), if present, is at least 95:5.