IP Library Granted Patent US 8,679,461
Granted Patent B2
US 8,679,461 · App. 11/996,765 · Granted Mar 25, 2014

Use of hesperetin for enhancing the sweet taste

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Quick Facts
Patent No.
US 8,679,461
App. No.
11/996,765
Granted
Mar 25, 2014
Kind
B2
Abstract

The use of hesperetin of formula (I) is described wherein the hesperetin of formula (I) is in the form of a (2S)-enantiomer, (2R)-enantiomer or any desired mixture of the two enantiomers, a salt of hesperetin of formula (I), —a mixture comprising or consisting of two or more salts of the hesperetin of formula (I), or a mixture comprising or consisting of hesperetin of formula (I) and one or more salts of hesperetin of formula (I) for enhancing the sweet taste of a sweet-tasting substance or sweet olfactory impression of a flavoring which gives a sweet olfactory impression.

Claims (38)

1. A preparation comprising:

(a) 0.1 to 500 ppm of hesperetin, or a salt thereof;

(b) one or more sweet-tasting substances selected from the group consisting of sucrose, lactose, glucose, D-tagatose, fructose, and sugar alcohols;

wherein the (a) hesperetin, or salt thereof, and the (b) one or more sweet-tasting substances in the preparation are in amounts such that the sweet taste impression of the preparation is enhanced by at least 20%, in comparison to a preparation with an otherwise identical composition without the (a) hesperetin, or salt thereof.

2. The preparation according to claim 1 , wherein the (b) one or more sweet-tasting substances is selected from the group consisting of sucrose, lactose, glucose, D-tagatose, and fructose.

3. The preparation according to claim 2 , wherein the (b) one or more sweet-tasting substances is sucrose.

4. The preparation according to claim 1 , further comprising:

(c) one or more flavorings that give a sweet olfactory impression.

5. The preparation according to claim 2 , wherein the (c) one or more flavoring that give a sweet olfactory impression are selected from the group consisting of vanillin, ethylvanillin, ethylvanillin isobutyrate (3-ethoxy-4-isobutyryloxybenzaldehyde), 2,5-dimethyl-4-hydroxy-3(2H)-furanone and derivatives, homofuronol (2-ethyl-5-methyl-4-hydroxy-3(2H)-furanone and 5-ethyl-2-methyl-4-hydroxy-3(2H)-furanone), maltol and derivatives, coumarin and derivatives, gamma-lactones, delta-lactones, methyl sorbate, divanillin, 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)furanone, 2-hydroxy-3-methyl-2-cyclopentenone, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, fruit esters and fruit lactones, 4-(p-hydroxyphenyl)-2-butanone, 1,1-dimethoxy-2,2,5-trimethyl-4-hexan, 2,6-dimethyl-5-hepten-1-al, phenylacetaldehyde, and mixtures thereof.

6. The preparation according to claim 1 comprising:

(a) 0.1 to 250 ppm of hesperetin, or a salt thereof.

7. The preparation according to claim 1 , wherein the (a) hesperetin, or salt thereof, and the (b) one or more sweet-tasting substances in the preparation are in amounts such that the sweet impression of the preparation is enhanced by at least 40%, in comparison to a preparation with an otherwise identical composition without the (a) hesperetin, or salt thereof.

8. The preparation of claim 1 , further comprising:

(d) one or more esters selected from the group consisting of lactic acid-C 1 -C 6 -esters, tartaric acid-di-C 1 -C 4 -esters, succinic acid-di-C 1 -C 4 -esters, malonic acid-di-C 1 -C 4 -esters, malic acid-di-C 1 -C 4 -esters, citric acid-di-C 1 -C 4 -esters, and citric acid-tri-C 1 -C 4 -esters; and optionally further comprises one or more 1,2-propylene glycol, dimethylsulphoxide, lactic acid, ethanol, ethanol/water mixtures, or mixtures thereof, as solvents.

9. The preparation of claim 1 , further comprising at least one substance for masking or avoiding a bitter, metallic, chalky, acidic, or astringent taste impression.

10. The preparation of claim 1 , further comprising at least one additional substance for enhancing a sweet, salty, or savory taste impression.

11. The preparation of claim 1 , further comprising a 4-hydroxydihydrochalcone, or a salt thereof, other than (a) hesperetin, or a salt thereof, wherein the 4-hydroxydihydrochalcone has the following formula:

R 1 , R 2 , R 3 , and R 4 are, independently of one another, H, OH, or C 1 -C 4 alkoxy, provided that at least one of R 1 , R 2 , and R 3 is OH.

12. The preparation of claim 1 , wherein the preparation is selected from the group consisting of:

(A) a confectionery;

(B) an alcoholic or non-alcoholic drink;

(C) a cereal or nut product;

(D) a milk product;

(E) a fruit and/or vegetable preparation;

(F) a product based on fat and oil or emulsions thereof; and

(G) an oral hygiene product.

13. The preparation of claim 1 , wherein said preparation is spray-dried.

14. A preparation comprising:

(a) 0.1 to 500 ppm of hesperetin, or a salt thereof;

(b) sucrose;

wherein the (a) hesperetin, or salt thereof, and the (b) sucrose in the preparation are in amounts such that the sweet taste impression of the preparation is enhanced by at least 40%, in comparison to a preparation with an otherwise identical composition without the (a) hesperetin, or salt thereof.

15. A method for enhancing the sweet taste impression of a preparation comprising including in the preparation:

(a) 0.1 to 500 ppm of hesperetin, or a salt thereof; and

(b) one or more sweet-tasting substances selected from the group consisting of sucrose, lactose, glucose, D-tagatose, fructose, and sugar alcohols;

wherein the (a) hesperetin, or salt thereof, and the (b) one or more sweet-tasting substances in the preparation are in amounts such that the sweet taste impression of the preparation is enhanced by at least 20%, in comparison to a preparation with an otherwise identical composition without the (a) hesperetin, or salt thereof.

16. The method according to claim 15 , wherein the (b) one or more sweet-tasting substances is selected from the group consisting of sucrose, lactose, glucose, D-tagatose, and fructose.

17. The method according to claim 15 , wherein the (b) one or more sweet-tasting substances is sucrose.

18. The preparation according to claim 15 , wherein the (a) hesperetin, or salt thereof, and the (b) one or more sweet-tasting substances in the preparation are in amounts such that the sweet taste impression of the preparation is enhanced by at least 40%, in comparison to a preparation with an otherwise identical composition without the (a) hesperetin, or salt thereof.

Assignments (2)
MERGER Recorded Apr 22, 2011
From: SYMRISE GMBH & CO. KG
To: SYMRISE AG
Reel/Frame 026171/0582 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2008
From: LEY, JAKOB; KINDEL, GUNTER; PAETZ, SUSANNE; REISS, THOMAS; HAUG, MARTIN; SCHMIDTMANN, RALPH; KRAMMER, GERHARD
To: SYMRISE GMBH & CO. KG
Reel/Frame 021360/0517 →