Substituted cyclopropanecarboxylic acid (3-methyl-cyclohexyl)amide as flavoring substance

1. A compound of formula (I) or a mixture of compounds of formula (I)

wherein:

R 1 , R 2 , and R 3 are independently H or an alkyl group having 1 to 3 C-atoms, wherein at least one of R 1 , R 2 , and R 3 is not H;

R 4 is H, an alkyl group having 1 to 6 C-atoms, or an alkenyl group having 2 to 6 C-atoms;

R 5 , R 6 , R 7 , and R 8 are independently H or methyl; and

R 9 is H, an alkyl group having 5 to 12 C-atoms, or an alkenyl group having 5 to 12 C-atoms;

with the proviso that compounds of formula (III),

are excluded.

2. A compound according to claim 1 or a mixture of the compounds according to claim 1 , wherein the compound or the compounds are selected from the group consisting of:

(1R,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (1), (1R,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (2), (1S,3R)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (3), (1S,3R)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (4), (1S,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (5), (1S,3S)-2,2-dimethyl-3-(2-methyl-propenyl)cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (6), (1R,3R)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (7), and (1R,3R)-2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)amide (8).

3. A compound according to claim 1 or a mixture of the compounds according to claim 1 , wherein the compound or the compounds of formula (I) is a compound or compounds of formula (II)

and wherein:

R 1 is alkyl group having 1 to 3 C-atoms; and

R 9 is H, an alkyl group having 5 to 12 C-atoms, or an alkenyl group having 5 to 12 C-atoms.

4. A compound according to claim 3 or a mixture of the compounds according to claim 3 , wherein the compound or the compounds of formula (II) is a compound or are compounds selected from the group consisting of:

cyclopropanecarboxylic acid((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (9),

cyclopropanecarboxylic acid((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (10),

cyclopropanecarboxylic acid((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (11),

cyclopropanecarboxylic acid((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (12),

cyclopropanecarboxylic acid((1R,2R,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (13),

cyclopropanecarboxylic acid((1S,2S,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (14),

cyclopropanecarboxylic acid((1S,2R,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (15), and

cyclopropanecarboxylic acid((1R,2S,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (16).

5. A composition suitable for consumption, comprising:

a flavorfully effective amount of one or more compounds of formula (I) according to claim 1 , and

one or more ingredients suitable for consumption.

6. A composition according to claim 5 , wherein the further ingredients are:

solid carrier substances or

solid carrier substances and flavoring components or

water, an oil phase, optionally one or more W/O emulsifiers, one or more antioxidants and optionally, one or more substances for enhancing an antioxidative effect.

7. A composition according to claim 6 , wherein the further ingredients are solid carrier substances, and the weight ratio of total amount of the compounds of formula (I) according to claim 1 , to the solid carrier substances is in a range from 1:10 to 1:100000 based on the dry weight of the composition.

8. A composition according to claim 7 , comprising:

0.01 to 0.1 wt % of one or more compounds of formula (I),

5 to 30 wt % of water,

50 to 90 wt % of an oil phase,

0.1 to 5 wt % of consumable W/O emulsifier and

optionally, one or more antioxidants and, optionally, one or more substances for enhancing an antioxidative effect.

9. The composition according to claim 5 , further comprising a substance for masking or reducing an unpleasant taste impression and/or a substance for enhancing the pleasant taste impression of a pleasantly tasting substance.

10. A (i) ready-to-use or ready-to-consume preparation or (ii) semi-finished goods used for nourishment, oral hygiene or enjoyment, comprising

a flavorfully effective amount of one or more compounds of formula (I)

wherein:

R 1 , R 2 , and R 3 are independently H or an alkyl group having 1 to 3 C-atoms, wherein at least one of R 1 , R 2 , and R 3 is not H;

R 4 is H, an alkyl group having 1 to 6 C-atoms, or an alkenyl group having 2 to 6 C-atoms;

R 5 , R 6 , R 7 , and R 8 are independently H or methyl; and

R 9 is H, an alkyl group having 5 to 12 C-atoms, or an alkenyl group having 5 to 12 C-atoms;

wherein the compound or mixture of compounds is a flavoring substance or a mixture of flavoring substances.

11. A ready-to-use or ready-to-consume preparation used for nourishment, oral hygiene or enjoyment according to claim 10 , comprising 0.01 ppm to 100 ppm of one or more compounds of formula (I), based on the total weight of the ready-to-consume preparation.

12. A composition, preparation or semi-finished goods according to claim 10 , further comprising a substance for masking or reducing an unpleasant taste impression and/or a substance for enhancing the pleasant taste impression of a pleasantly tasting substance.

13. A method for creating, modifying or enhancing a taste in a (i) ready-to-consume preparation or (ii) semi-finished goods used for nourishment or enjoyment, comprising the following steps:

mixing a flavorfully effective amount of one or more compounds of formula (I) according to claim 1 with one or more further ingredients of (i) a ready-to-consume preparation or (ii) semi-finished goods

and/or

applying a flavorfully effective amount of one or more compounds of formula (I) according to claim 1 to one or more further ingredients of (i) ready-to-consume preparation or (ii) semi-finished goods

and/or

embedding a flavorfully effective amount of one or more compounds of formula (I) according to claim 1 in a cladding material or a matrix material.

14. The method according to claim 13 , further comprising creating, modifying or enhancing an Umami-taste.

15. A method for preparing a compound of formula (11) and/or (12), or a mixture comprising the compound of formula (11) and/or (12), comprising the following steps:

(a) carrying out a Leuckart-Wallach reaction, starting from enantiomerically pure or racemic menthone to produce a corresponding formamide of formula (III),

(b) carrying out a fractional crystallization of the neo-menthyl formamides (formula (IV) and/or (V))

(c) saponifying the neo-menthyl formamides with a strong acid to produce amine (VI) and/or (VII), and

(d) reacting the amine VI and/or VII either with (i) cyclopropanecarboxylic acid chloride or with (ii) cyclopropanecarboxylic acid to produce (11) and/or (12)

16. A method for flavoring a material comprising adding to the material a compound of Formula (I) or a mixture of compounds of formula (I)

wherein:

R 1 , R 2 , and R 3 are independently H or an alkyl group having 1 to 3 C-atoms, wherein at least one of R 1 , R 2 , and R 3 is not H;

R 4 is H, an alkyl group having 1 to 6 C-atoms, or an alkenyl group having 2 to 6 C-atoms;

R 5 , R 6 , R 7 , and R 8 are independently H or methyl; and

R 9 is H, an alkyl group having 5 to 12 C-atoms, or an alkenyl group having 5 to 12 C-atoms;

wherein the compound or mixture of compounds is a flavoring substance or a mixture of flavoring substances.

17. The method according to claim 16 , wherein the compound or the compounds of formula (I) is a compound or are compounds selected from the group consisting of:

(1R,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (1), (1R,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (2), (1S,3R)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (3), (1S,3R)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (4), (1S,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (5), (1S,3S)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (6), (1R,3R)-2,2-dimethyl-3-(2-methyl-propenyl)-cyclopropanecarboxylic acid-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (7), and (1R,3R)-2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylic acid-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (8).

18. The method according to claim 16 , wherein the compound or the compounds of formula (I) is a compound or are compounds of formula (II)

and wherein:

R 1 is an alkyl group having 1 to 3 C-atoms; and

R 9 is H, an alkyl group having 5 to 12 C-atoms, or an alkenyl group having 5 to 12 C-atoms.

19. The method according to claim 18 , wherein the compound or the compounds of formula (II) is a compound or are compounds selected from the group consisting of:

Cyclopropanecarboxylic acid ((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (9),

Cyclopropanecarboxylic acid ((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (10),

Cyclopropanecarboxylic acid ((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (11),

Cyclopropanecarboxylic acid ((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (12),

Cyclopropanecarboxylic acid ((1R,2R,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (13),

Cyclopropanecarboxylic acid ((1S,2S,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (14),

Cyclopropanecarboxylic acid ((1S,2R,5R)-2-isopropyl-5-methyl-cyclohexyl)-amide (15), and

Cyclopropanecarboxylic acid ((1R,2S,5S)-2-isopropyl-5-methyl-cyclohexyl)-amide (16).