Steviol glycoside compositions with reduced surface tension

Patent metadata

Field	Value
Publication number	US-11701400-B2
Application number	US-201916374388-A
Country	US
Kind code	B2
Filing date	Apr 3, 2019
Priority date	Oct 6, 2017
Publication date	Jul 18, 2023
Grant date	Jul 18, 2023

Abstract

A steviol glycoside composition with reduced surface tension. The reduced surface tension steviol glycoside composition includes an aqueous solution of a steviol glycoside and a surface tension reducing compound in an amount effective to reduce surface tension. Method for reducing surface tension in a steviol glycoside solution includes contacting a steviol glycoside and a surface tension reducing compound.

First claim

The invention claimed is:

1. A steviol glycoside composition with reduced surface tension, the composition comprising an aqueous solution of:
a steviol glycoside; and
at least 1% by weight of a surface tension reducing compound, the surface tension reducing compound comprising
(i) one or more monocaffeoylquinic acids or salts thereof;
(ii) at least 10% by weight of one or more dicaffeoylquinic acids or salts thereof and
(iii) at least one of an ester of ferulic acid and quinic acid, an ester of sinapic acid and quinic acid, an ester of p-coumaric acid and quinic acid, an ester of caffeic acid and 3-(3,4-dihydroxyphenyl)lactic acid, an ester of caffeic acid and tartaric acid, and isomers thereof,
wherein the aqueous solution comprises a 1:0.5 to 1:4 ratio by weight of steviol glycoside to the surface tension reducing compound.

2. The composition of claim 1 , wherein the surface tension reducing compound comprise at least one of neochlorogenic acid, cryptochlorogenic acid, 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, 3-O-feruloylquinic acid, 4-0-feruloylquinic acid, 5-0-feruloylquinic acid, 3,4-diferuloylquinic acid, 3,5-diferuloylquinic acid, 4,5-diferuloylquinic acid, rosmarinic acid, cichoric acid, caftaric acid, monocaffeoyltartaric acid, dicaffeoyltartaric acid and isomers thereof.

3. The composition of claim 1 , wherein the surface tension reducing compound comprises at least 20% by weight of one or more dicaffeoylquinic acids or salts thereof.

4. The composition of claim 1 , wherein the surface tension reducing compound comprises at least 40% dicaffeoylquinic acids or salts thereof.

5. The composition of claim 1 , wherein the composition comprises between about 100 ppm and about 5000 ppm steviol glycoside.

6. The composition of claim 1 , wherein the composition comprises rebaudioside D or rebaudioside M.

7. The composition of claim 1 , wherein the steviol glycoside comprises between about 50% to about 95% rebaudioside M.

8. The composition of claim 1 , wherein the steviol glycoside comprises between about 5% and about 25% rebaudioside D.

9. The composition of claim 1 , wherein the total steviol glycoside concentration is at least 1% by weight.

10. The composition of claim 1 , wherein the aqueous solution comprises a 1:1 to 1:3 ratio by weight of steviol glycoside to the surface tension reducing compound.

11. The composition of claim 1 , wherein the aqueous solution comprises a 1:1 to 1:3 ratio by weight of steviol glycoside to total concentration of esters of caffeic acid and quinic acid, esters of ferulic acid and quinic acid, esters of sinapic acid and quinic acid, esters of p-coumaric acid and quinic acid, esters of caffeic acid and 3-(3,4-dihydroxyphenyl)lactic acid, and esters of caffeic acid and tartaric acid.

12. A beverage comprising the composition of claim 1 .

13. A beverage concentrate solution with reduced surface tension, the solution comprising:
a steviol glycoside; and
a surface tension reducing compound in an amount effective to reduce surface tension by at least 10% during at least six-fold dilution of the concentrate, the surface tension reducing compound comprising
(i) one or more monocaffeoylquinic acids or salts thereof;
(ii) at least 10% by weight of one or more dicaffeoylquinic acids or salts thereof and
(iii) at least one of an ester of ferulic acid and quinic acid, an ester of sinapic acid and quinic acid, an ester of p-coumaric acid and quinic acid, an ester of caffeic acid and 3-(3,4-dihydroxyphenyl)lactic acid, an ester of caffeic acid and tartaric acid, and isomers thereof,
wherein the solution comprises a 1:0.5 to 1:4 ratio by weight of steviol glycoside to the surface tension reducing compound.

14. The solution of claim 13 , wherein the solution comprises about 2400 to about 4200 ppm steviol glycoside.

15. The solution of claim 13 , wherein the solution comprises about 1800 to about 5400 ppm surface tension reducing compound.

16. The solution of claim 13 , wherein the solution comprises a 1:1 to 1:3 ratio by weight of steviol glycoside to total concentration of esters of caffeic acid and quinic acid, esters of ferulic acid and quinic acid, esters of sinapic acid and quinic acid, esters of p-coumaric acid and quinic acid, esters of caffeic acid and 3-(3,4-dihydroxyphenyl)lactic acid, and esters of caffeic acid and tartaric acid.

17. The solution of claim 13 , wherein the surface tension reducing compound comprises at least 20% dicaffeoylquinic acid.

18. The solution of claim 13 , wherein the steviol glycoside comprises greater than 80% rebaudioside M and rebaudioside D.

19. The solution of claim 13 , wherein the solution additionally includes a buffer and has a pH between 1 . 5 and 4 .

20. A method for reducing surface tension in a steviol glycoside composition, the method comprising:
adding to a solution comprising a steviol glycoside a surface tension reducing compound comprising (i) one or more monocaffeoylquinic acids or salts thereof; (ii) at least 10% by weight of one or more dicaffeoylquinic acids or salts thereof; and (iii) at least one of an ester of ferulic acid and quinic acid, an ester of sinapic acid and quinic acid, an ester of p-coumaric acid and quinic acid, an ester of caffeic acid and 3-(3,4-dihydroxyphenyl)lactic acid, an ester of caffeic acid and tartaric acid, and isomers thereof, wherein the surface tension reducing compound is added in an amount such that the resulting composition comprises a 1:0.5 to 1:4 ratio by weight of steviol glycoside to the surface tension reducing compound and such that the resulting composition comprises at least 1% by weight of the surface tension reducing compound.

Assignees

• Cargill Inc

Inventors

• Gaspard Dan S
• Steinbach Adam John
• Zarth Adam T

Classifications

• A61K31/192

  having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid  {(cannabinoids A61K31/658)} · CPC title

• A61K36/28 Primary

  Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea · CPC title

• A23L27/36 Primary

  Terpene glycosides · CPC title

• A23F3/34

  Tea substitutes, e.g. matè; Extracts or infusions thereof · CPC title

• A23L2/56

  Flavouring or bittering agents (sweeteners A23L2/60) · CPC title