Steviol glycoside compositions with reduced surface tension

Patent metadata

Field	Value
Publication number	US-12097231-B2
Application number	US-202318328066-A
Country	US
Kind code	B2
Filing date	Jun 2, 2023
Priority date	Oct 6, 2017
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

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 method for reducing surface tension in a steviol glycoside solution, the method comprising:
adding one or more steviol glycosides and a surface tension reducing compound to an aqueous solution to form a steviol glycoside solution; wherein surface tension of the steviol glycoside solution is reduced relative to an equivalent solution lacking the surface tension reducing compound;
wherein the surface tension reducing compound comprises:
(i) one or more monocaffeoylquinic acids or salts thereof;
(ii) at least 20% (wt) 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; and

wherein the one or more steviol glycosides and the surface tension reducing compound are added such that the steviol glycoside solution comprises a 1:0.5 to 1:4 ratio by weight of steviol glycose to surface tension reducing compound.

2. The method of claim 1 , wherein surface tension is reduced by at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80% or at least 90% compared to a steviol glycoside solution without the surface tension reducing compound.

3. The method of claim 1 , wherein the surface tension reducing compound comprises at least 30% (wt) of a total of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof.

4. The method of claim 1 , wherein the one or more monocaffeoylquinic acids or salts thereof comprise one or more of neochlorogenic acid, cryptochlorogenic acid, 1,3-dicaffeoylquinic acid, and salts thereof.

5. The method of claim 1 , wherein the surface tension reducing compound comprises one or more of 3-O-feruloylquinic acid, 4-O-feruloylquinic acid, 5-O-feruloylquinic acid, 3,4-diferuloylquinic acid, 3,5-diferuloylquinic acid, 4,5-diferuloylquinic acid, and salts thereof.

6. The method of claim 1 , wherein the steviol glycoside solution comprises between about 100 ppm and about 5000 ppm steviol glycoside.

7. The method of claim 1 , wherein the one or more steviol glycosides comprises rebaudioside D, rebaudioside M, or combination thereof.

8. The method of claim 1 , wherein the steviol glycoside solution comprises between 50 wt % and 95 wt % rebaudioside M based on total weight of steviol glycosides in the solution.

9. The method of claim 1 , wherein the steviol glycoside solution comprises between 5 wt % and 25 wt % rebaudioside D based on total weight of steviol glycosides in the solution.

10. The method of claim 1 , wherein the steviol glycoside solution comprises at least 1 wt % steviol glycosides.

11. The method of claim 1 , wherein the steviol glycoside solution comprises a 1:1 to 1:3 ration by weight of steviol glycoside to surface tension reducing compound.

12. The method 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.

13. The method of claim 1 , additionally comprising the step of preparing a beverage comprising the steviol glycoside solution.

14. A method for preparing a beverage concentrate solution with reduced surface tension, the method comprising:
adding to an aqueous solution i) one or more steviol glycosides and ii) a surface tension reducing compound to form a beverage concentrate solution, wherein the beverage concentrate solution has reduced surface tension relative to an equivalent beverage concentrate solution lacking the surface tension reducing compound;
wherein the surface tension reducing compound comprises:
(i) one or more monocaffeoylquinic acids or salts thereof;
(ii) at least 20% (wt) 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; and

wherein the one or more steviol glycosides and the surface tension reducing compound are added such that the beverage concentrate solution comprises a 1:0.5 to 1:4 ratio by weight of steviol glycose to surface tension reducing compound.

15. The method of claim 14 , wherein the beverage concentrate solution comprises 2400 to 4200 ppm of total steviol glycoside.

16. The method of claim 14 , wherein the beverage concentrate solution comprises 1800 to 5400 ppm surface tension reducing compound.

17. The method of claim 14 , wherein the beverage concentrate solution includes a buffer and has a pH between 1.5 and 4.

18. The method of claim 14 , wherein surface tension is reduced by at least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80% or at least 90% compared to a steviol glycoside solution without the surface tension reducing compound.

19. The method of claim 14 , wherein the surface tension reducing compound comprises at least 30% (wt) of a total of 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and salts thereof.

20. The method of claim 14 , wherein the one or more steviol glycosides comprises rebaudioside D, rebaudioside M, or combination thereof.

21. The method of claim 14 , wherein the steviol glycoside solution comprises between 50 wt % and 95 wt % rebaudioside M and 5 wt % and 25 wt % rebaudioside D based on total weight of steviol glycosides in the solution.

22. The method of claim 14 , wherein the steviol glycoside solution comprises at least 1 wt % steviol glycosides.

23. The method of claim 14 , 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.

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

• B01D15/361

  Ion-exchange · CPC title

• A61K2236/39

  Complex extraction schemes, e.g. fractionation or repeated extraction steps · CPC title