Specific vanillyl lignans and use thereof as taste improvers

Patent metadata

Field	Value
Publication number	US-9545119-B2
Application number	US-201214114189-A
Country	US
Kind code	B2
Filing date	Apr 24, 2012
Priority date	Apr 29, 2011
Publication date	Jan 17, 2017
Grant date	Jan 17, 2017

Abstract

The invention relates to the use of specific compounds from the structural class of vanillyl lignans or the salts and/or mixtures thereof for modifying or masking unpleasant taste impressions, in particular bitter, astringent, and/or metallic taste impressions. The invention also relates to a corresponding method for masking unpleasant taste impressions, in particular bitter, astringent, and/or metallic taste impressions. The invention further relates to specific preparations containing an effective amount of vanillyl lignans or the salts and/or mixtures thereof to be used in accordance with the invention.

First claim

The invention claimed is:

1. A method for masking a bitter, an astringent, and/or a metallic taste of caffeine, theobromine, naringin, quinine hydrochloride dihydrate and/or salicin comprising combining the caffeine, theobromine, naringin, quinine hydrochloride dihydrate and/or salicin with one or more vanillyl lignans selected from the group consisting of:
(1-(−)) (−)-Matairesinol ((3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl[oxolan-2-one);
(2-(−)) (−)-7-hydroxymatairesinol ((3R,4R)-4-[(S)-hydroxy-(4-hydroxy-3-methoxy-phenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one);
(3-(+)) (+)-lariciresinol (4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxy-methyl)-oxolan-3-yl]methyl]-2-methoxyphenol);
(4-(−)) (−)-arctigenin ((3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxy-phenyl)m-ethyl[oxolan-2-one);
(5-(+)) (+)-isolariciresinol (1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-2,-3-naphthalenedimethanol);
(6-(−)) (−)-.alpha.-conidendrin ((3aR,9R,9aS)-7-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one);
(7-(−)) (−)-nortrachelogenin ((3S,4S)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-oxolan-2-on-e); and
(8-(+)) (+)-pinoresinol (4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydro-furo[3,4-c]furan-3-yl]-2-methoxyphenol),
wherein the stereoisomer purity is greater than 50% relative to all the stereoisomers of the respective vanillyl lignin(s).

2. The method of claim 1 , wherein the stereoisomer purity is greater than 80% relative to all the stereoisomers of the respective vanillyl lignin(s).

3. The method of claim 1 , wherein the total quantity of vanillyl lignans is in the range of 10 mg/kg to less than 300 mg/kg.

4. The method of claim 1 , wherein the total quantity of vanillyl lignans is in the range of 12 mg/kg to 100 mg/kg.

5. The method of claim 1 for masking a bitter, an astringent, and/or a metallic taste of caffeine.

6. The method of claim 1 for masking a bitter, an astringent, and/or a metallic taste of theobromine.

7. The method of claim 1 for masking a bitter, an astringent, and/or a metallic taste of naringin.

8. The method of claim 1 for masking a bitter, an astringent, and/or metallic taste of quinine hydrochloride dehydrate.

9. The method of claim 1 for masking a bitter, an astringent, and/or metallic taste of salicin.

10. A preparation comprising caffeine, theobromine, naringin, quinine hydrochloride dihydrate and/or salicin and one or more vanillyl lignans selected from the group consisting of:
(1-(−)) (−)-Matairesinol ((3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one);
(2-(−)) (−)-7-hydroxymatairesinol ((3R,4R)-4-[(S)-hydroxy-(4-hydroxy-3-methoxy-phenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one);
(3-(+)) (+)-lariciresinol (4-[[(3R,4R,5S)-5-(4-hydroxy-3-methoxyphenyl)-4-(hydroxy-methyl)-oxolan-3-yl]methyl]-2-methoxyphenol);
(4-(−)) (−)-arctigenin ((3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxy-phenyl)m-ethyl[oxolan-2-one);
(5-(+)) (+)-isolariciresinol (1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-2,-3-naphthalenedimethanol);
(6-(−)) (−)-.alpha.-conidendrin ((3aR,9R,9aS)-7-hydroxy-9-(4-hydroxy-3-methoxyphenyl)-6-methoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one);
(7-(−)) (−)-nortrachelogenin ((3S,4S)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-oxolan-2-on-e); and
(8-(+)) (+)-pinoresinol (4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydro-furo[3,4-c]furan-3-yl]-2-methoxyphenol),
wherein the stereoisomer purity is greater than 50% relative to all the stereoisomers of the respective vanillyl lignin(s).

11. The preparation of claim 10 , wherein the stereoisomer purity is greater than 80% relative to all the stereoisomers of the respective vanillyl lignin(s).

12. The preparation of claim 10 , wherein the total quantity of vanillyl lignans is in the range of 10 mg/kg to less than 300 mg/kg.

13. The preparation of claim 10 , wherein the total quantity of vanillyl lignans is in the range of 12 mg/kg to 100 mg/kg.

14. The preparation of claim 10 comprising caffeine.

15. The preparation of claim 10 comprising theobromine.

16. The preparation of claim 10 comprising naringin.

17. The preparation of claim 10 comprising quinine hydrochloride dehydrate.

18. The preparation of claim 10 comprising salicin.

19. The preparation of claim 10 comprising:
at least 0.05% by weight of caffeine;
at least 0.05% by weight of theobromine; or
at least 0.05% by weight of naringin.

20. The preparation of claim 10 comprising:
1% to 2.5% by weight of caffeine;
1% to 2.5% by weight of theobromine; or
0.2% to 2% by weight of naringin.

Assignees

• Backes Michael
• Ley Jakob Peter
• Reichelt Katharina
• Paetz Susanne
• Symrise Ag

Inventors

• Backes Michael
• Ley Jakob Peter
• Reichelt Katharina
• Paetz Susanne

Classifications

• A23L27/10 Primary

  Natural spices, flavouring agents or condiments; Extracts thereof · CPC title

• A23L27/84

  Flavour masking or reducing agents · CPC title

• A23L27/86

  Addition of bitterness inhibitors · CPC title

• A23L1/22075 Primary

  Human Necessities · mapped topic