IP Library Granted Patent US 12662505
Granted Patent B2
US 12662505 · App. 17/594,136 · Granted Jun 23, 2026

Steviol glycoside solubility enhancers

Inventors: Dan S. Gaspard (Victoria, MN); Adam T. Zarth (St. Louis Park, MN)
Assignee: CARGILL, INCORPORATED
C07H15/256A23L2/60A23L27/36
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Quick Facts
Patent No.
US 12662505
App. No.
17/594,136
Granted
Jun 23, 2026
Kind
B2
Abstract

A steviol glycoside solubility enhancer may include a monocaffeoylquinic (MCQ) component that includes at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and a dicaffeoylquinic (DCQ) component that includes at least one compound selected from the group consisting 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. In one suitable implementation, the MCQ component and the DCQ component together comprise more than 50% (wt), preferably more than 60% (wt), more than 70% (wt), more than 80% (wt), more than 90% (wt), or more than 95% (wt) of the steviol glycoside solubility enhancer.

Claims (39)

1 . An aqueous steviol glycoside solution comprising:

one or more steviol glycosides; and

a steviol glycoside solubility enhancer comprising

a monocaffeoylquinic (MCQ) component that includes at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and

a dicaffeoylquinic (DCQ) component that includes at least one compound selected from the group consisting 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;

wherein the MCQ component and the DCQ component together comprise more than 60% (wt) of the steviol glycoside solubility enhancer; and

wherein a weight ratio of the DCQ component to the MCQ component is at least 1;

wherein solubility of the one or more steviol glycosides in the aqueous steviol glycoside solution is higher than an equivalent solution lacking the steviol glycoside solubility enhancer; and

wherein when the aqueous steviol glycoside solution comprises at least 2% (wt) steviol glycoside and the one or more steviol glycosides remains in solution for at least 10 days when stored at 22° C.

2 . The aqueous steviol glycoside solution of claim 1 , wherein the MCQ component and the DCQ component together comprise more than 70% (wt) of the steviol glycoside solubility enhancer.

3 . The aqueous steviol glycoside solution of claim 1 , wherein the MCQ component and the DCQ component together comprise more than 80% (wt) of the steviol glycoside solubility enhancer.

4 . The aqueous steviol glycoside solution of claim 1 , wherein the MCQ component and the DCQ component together comprise more than 90% (wt) of the steviol glycoside solubility enhancer.

5 . The aqueous steviol glycoside solution of claim 1 , wherein the steviol glycoside solubility enhancer further comprising one or more compounds selected from the group consisting of caffeic acid, ferulic acid, p-coumaric acid, sinapic acid, quinic acid, 3-(3,4-dihydroxyphenyl) lactic acid, tartaric acid, chicoric acid, caftaric acid, monoferuloylquinic acids, diferuloylquinic acids, monocoumaroylquinic acids, dicoumaroylquinic acids, and salts thereof.

6 . The aqueous steviol glycoside solution of claim 1 , wherein the steviol glycoside solubility enhancer further comprising one or more compounds selected from the group consisting of caffeic acid, monoferuloylquinic acids, diferuloylquinic acids, and salts thereof.

7 . The aqueous steviol glycoside solution of claim 1 , wherein the weight ratio of the DCQ component to the MCQ component is between 1 and 20.

8 . The aqueous steviol glycoside solution of claim 1 , wherein solution comprises at least 2% (wt) steviol glycoside and the one or more steviol glycosides remains in solution for at least 10 days when stored at 22° C.

9 . The aqueous steviol glycoside solution of claim 1 , wherein solution comprises at least 3% (wt) steviol glycoside and the one or more steviol glycosides remains in solution for at least 10 days when stored at 22° C.

10 . The aqueous steviol glycoside solution of claim 1 , wherein solution comprises at least 5% (wt) steviol glycoside and the one or more steviol glycosides remains in solution for at least 10 days when stored at 22° C.

11 . The aqueous steviol glycoside solution of claim 1 , wherein the one or more steviol glycosides comprises rebaudioside M, rebaudioside D, or combinations thereof.

12 . The aqueous steviol glycoside solution of claim 1 , wherein the solution comprises at least 2% (wt) of a combination of rebaudioside M and rebaudioside D.

13 . The aqueous steviol glycoside solution of claim 1 , wherein the solution comprises at least 2% (wt) of a combination of rebaudioside M and rebaudioside D, and the combination of rebaudioside M and rebaudioside D are at least 75% (wt) of total steviol glycosides in the aqueous steviol glycoside solution.

14 . The aqueous steviol glycoside solution of claim 1 , wherein the solution comprises at least 2% (wt) of a combination of rebaudioside M and rebaudioside D, and the combination of rebaudioside M and rebaudioside D are at least 80% (wt) of total steviol glycosides in the aqueous steviol glycoside solution.

15 . The aqueous steviol glycoside solution of claim 1 , wherein the solution comprises at least 2% (wt) of a combination of rebaudioside M and rebaudioside D, and the combination of rebaudioside M and rebaudioside D are at least 90% (wt) of total steviol glycosides in the aqueous steviol glycoside solution.

16 . The aqueous steviol glycoside solution of claim 1 , wherein ratio of total steviol glycosides to steviol glycoside solubility enhancer is between 1:1 and 1:2.

17 . The aqueous steviol glycoside solution of claim 1 , wherein the solution comprises 1% (wt) to 10% (wt) steviol glycoside.

18 . The aqueous steviol glycoside solution of claim 1 , wherein the solution comprises 100 ppm to 900 ppm of the steviol glycoside solubility enhancer.

19 . The aqueous steviol glycoside solution of claim 1 , wherein steviol glycoside solubility enhancer comprises at least 50% (wt) of the DCQ component.

20 . The aqueous steviol glycoside solution of claim 1 , wherein steviol glycoside solubility enhancer comprises at least 60% (wt) of the DCQ component.

21 . The aqueous steviol glycoside solution of claim 1 , wherein steviol glycoside solubility enhancer comprises at least 70% (wt) of the DCQ component.

22 . A non-alcoholic beverage comprising the aqueous steviol glycoside solution of claim 1 and having a pH of between 1.5 and 4.

23 . An aqueous steviol glycoside solution comprising:

at least 2.0 wt % of total steviol glycosides comprising rebaudioside M and rebaudioside D; and

a steviol glycoside solubility enhancer comprising

a monocaffeoylquinic (MCQ) component that includes at least one compound selected from the group consisting of chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, and salts thereof; and

a dicaffeoylquinic (DCQ) component that includes at least one compound selected from the group consisting 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;

wherein the MCQ component and the DCQ component together comprise more than 60% (wt) of the steviol glycoside solubility enhancer; and

wherein a weight ratio of the DCQ component to the MCQ component is at least 1;

wherein solubility of the total steviol glycosides in the aqueous steviol glycoside solution is higher than an equivalent solution lacking the steviol glycoside solubility enhancer; and

wherein the total steviol glycosides remain in solution for at least 10 days when stored at 22° C.