Neo-Menthyl Derivatives as Flavor Materials

• US 20090311401A1
• Filed: 06/10/2009
• Published: 12/17/2009
• Est. Priority Date: 06/13/2008
• Status: Active Grant

• Current Assignee: Symrise AG
• Original Assignee: Symrise Gmbh & Co. Kg (Symrise AG)
• Inventors: Backes, Michael, Ley, Jakob Peter, Oertling, Heiko, Vossing, Tobias
• Granted Patent: US 8,852,664 B2
• Time in Patent Office: Days
• US Class Current: 426/533
• CPC Class Codes: A23L 27/20 Synthetic spices, flavouring agents or condiments
• CPC Class Codes: A23L 27/2024 having oxygen as the only hetero atom
• CPC Class Codes: A23L 27/2028 Carboxy compounds
• CPC Class Codes: A23L 27/88 Taste or flavour enhancing agents
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 271/34 with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 271/36 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 271/38 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 275/26 having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
• CPC Class Codes: C07C 335/14 having nitrogen atoms of thiourea groups bound to carbon atoms of rings other than six-membered aromatic rings

Abstract

The present invention relates primarily to the use of particular ureas, thioureas, carbamates, thiocarbamates and guanidines based on the neomenthyl structure and corresponding mixtures with one another or with further compounds as flavor materials or flavor material mixtures for producing, imparting, modifying and/or enhancing savory flavor notes. the invention furthermore relates to particular compositions, preparations and semifinished products which comprise the said compounds, as well as methods for producing, imparting, modifying and/or enhancing particular flavor impressions. Lastly, the invention also relates to the compounds themselves and to corresponding mixtures.

Claims

1. A method for preparing a flavor material or flavor material mixture, comprising adding a compound or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (I) and (ent-I)

2. The method as defined in the claim 1, wherein (i) the compound of formula (I) or (ent-I) or (ii) one, two, more than two or all compounds of the formulae (I) and (ent-I) in the mixture are selected from the group consisting of:

(1) 1-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-(3-methoxy-propyl)-urea,

(2) 1-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-3-(3-methoxy-propyl)-urea,

(3) 1-(3-hydroxy-propyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-urea,

(4) 1-(3-hydroxy-propyl)-3-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-urea,

(5) 1-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-(2-methoxy-1-methyl-ethyl)-urea,

(6) 1-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-3-(2-methoxy-1-methyl-ethyl)-urea,

(7) 3-[3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-ureido]-butyric acid ethyl ester,

(8) 3-[3-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-ureido]-butyric acid ethyl ester,

(9) (3-methoxy-propyl)-carbamic acid (1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester,

(10) (3-methoxy-propyl)-carbamic acid (1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester,

(11) 4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonylamino)-butyric acid ethyl ester

and

(12) 4-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylamino)-butyric acid ethyl ester.

3. The method as defined in claim 1, wherein the mixture contains one or more pairs of compounds of formulae (I) and (ent-I) or consists of one or more such pairs,

each pair consisting of a compound of the formula (I) and a compound of the formula (ent-I) as defined in claim 1,

wherein

the meanings of X and Y in the compound of formula (I) are respectively identical to the meanings of X and Y in the compound of formula (ent-I) and

wherein

(a) the meaning of Z in the compound of formula (I) is identical to the meaning of Z in the compound of formula (ent-I) or

(b) Z in the compound of formula (I) and Z in the compound of formula (ent-I) contain or one or more chiral centers and differ only by the absolute configuration at one, several or all of these chiral centers.

4. A method for preparing a mixture as a flavor material mixture, which consists of the following components or contains them, the method comprising combining:

(a) a compound selected from the group consisting of compounds of the formulae (I) and (ent-I) as defined in claim 1 or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (I) and (ent-I) as defined in claim 1;

and

(b) a compound selected from the group consisting of compounds of the formulae (II), (ent-II), (III), (ent-III), (IV), (ent-IV) or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (II), (ent-II), (III), (ent-III), (IV), (ent-IV);

5. The method as defined in claim 1, wherein the method produces, imparts, modifies and/or enhances an umami flavor and/or saltiness.

15. The method according to claim 3, wherein each pair is an enantiomer or epimer pair.

16. The method according to claim 4, wherein the flavor material mixture is at least 90:

10.

17. The method according to claim 4, wherein the flavor material mixture is at least 95:

5.

6. A single compound or mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (I) and (ent-I)

7. The single compound or mixture as defined in claim 6, wherein (i) the compound of formula (I) or (ent-I) or (ii) one, two, more than two or all compounds of the formulae (I) and (ent-I) in the mixture are selected from the group consisting of:

(1) 1-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-(3-methoxy-propyl)-urea,

(2) 1-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-3-(3-methoxy-propyl)-urea,

(3) 1-(3-hydroxy-propyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-urea,

(4) 1-(3-hydroxy-propyl)-3-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-urea,

(5) 1-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-3-(2-methoxy-1-methyl-ethyl)-urea,

(6) 1-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-3-(2-methoxy-1-methyl-ethyl)-urea,

(7) 3-[3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-ureido]-butyric acid ethyl ester,

(8) 3-[3-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl)-ureido]-butyric acid ethyl ester,

(9) (3-Methoxy-propyl)-carbamic acid (1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester,

(10) (3-methoxy-propyl)-carbamic acid (1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester,

(11) 4-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonylamino)-butyric acid ethyl ester

and

(12) 4-((1R,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxycarbonylamino)-butyric acid ethyl ester.

8. The mixture as defined in claim 6, wherein the mixture contains one or more pairs of compounds of formulae (I) and (ent-I) or consists of one or more such pairs, each pair consisting of a compound of the formula (I) and a compound of the formula (ent-I) as defined in claim 6,

wherein

the meanings of X and Y in the compound of formula (I) are respectively identical to the meanings of X and Y in the compound of formula (ent-I), and

wherein

(a) the meaning of Z in the compound of formula (I) is identical to the meaning of Z in the compound of formula (ent-I) or

(b) Z in the compound of formula (I) and Z in the compound of formula (ent-I) contain or one or more chiral centers and differ only by the absolute configuration at one, several or all of these chiral centers Z.

9. A mixture, which consists of the following components or contains them:

(a) a compound selected from the group consisting of compounds of the formulae (I) and (ent-I) as defined in claim 6 or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (I) and (ent-I) as defined in claim 6;

and

(b) a compound selected from the group consisting of compounds of the formulae (II), (ent-II), (III), (ent-III), (IV), (ent-IV) or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (II), (ent-II), (III), (ent-III), (IV), (ent-IV);

10. A composition, in particular composition suitable for consumption, comprising or consisting of

an effective flavoring amount of a compound or a mixture as defined in claim 6

and one or more further constituents suitable for consumption.

11. A method of preparing staple or luxury foods comprising adding compounds as defined in claim 6 or mixtures as defined in claim 6 in

(i) preparations ready for use or consumption or

(ii) semifinished products.

12. A preparation comprising compounds as defined in claim 6 or mixtures as defined in claim 6.

13. Semifinished products comprising compounds as defined in claim 6 or mixtures as defined in claim 6.

14. A method for producing, imparting, modifying and/or enhancing a flavor impression, wherein a compound as defined in claim 6 or a mixture as defined in claim 6 is added to a substance or composition in an effective flavoring amount.

18. The mixture according to claim 8, wherein each pair is an enantiomer or epimer pair.

19. A mixture, which consists of the following components or contains them:

(a) a compound selected from the group consisting of compounds of the formulae (I) and (ent-I) or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (I) and (ent-I) or containing a mixture as defined in claim 8;

and

(b) a compound selected from the group consisting of compounds of the formulae (II), (ent-II), (III), (ent-III), (IV), (ent-IV) or a mixture consisting of two or more compounds or containing one or more compounds selected from the group consisting of compounds of the formulae (II), (ent-II), (III), (ent-III), (IV), (ent-IV);

20. The mixture according to claim 19, wherein the flavor material mixture is at least 90:

10.

21. The mixture according to claim 19, wherein the flavor material mixture is at least 95:

5.

22. The mixture according to claim 9, wherein the flavor material mixture is at least 90:

10.

23. The method of claim 11, wherein the staple or luxury foods are sodium glutamate-reduced or -free preparations.

24. A method of preparing staple or luxury foods comprising adding compositions according to claim 10 in

(i) preparations ready for use or consumption or

(ii) semifinished products.

25. The method according to claim 24, wherein the staple or luxury foods are glutamate-reduced or -free preparations.

26. A preparation comprising compositions according to claim 10.

27. Semifinished products comprising compositions according to claim 10.

28. A method for producing, imparting, modifying and/or enhancing a flavor impression, wherein a composition as defined in claim 10 is added to a substance or composition in an effective flavoring amount.

29. A method for producing, imparting, modifying and/or enhancing a flavor impression, wherein a preparation as claimed in claim 12 is added to a substance or composition in an effective flavoring amount.

30. A method for producing, imparting, modifying and/or enhancing a flavor impression, wherein a semifinished product as claimed in claim 13 is added to a substance or composition in an effective flavoring amount.