Methods of isolating phenols from phenol-containing media

Patent metadata

Field	Value
Publication number	US-11548845-B2
Application number	US-202117470539-A
Country	US
Kind code	B2
Filing date	Sep 9, 2021
Priority date	Aug 26, 2019
Publication date	Jan 10, 2023
Grant date	Jan 10, 2023

Abstract

Methods of isolating phenols from phenol-containing media. The methods include combining a phospholipid-containing composition with the phenol-containing medium to generate a combined medium, incubating the combined medium to precipitate phenols in the combined medium and thereby form a phenol precipitate phase and a phenol-depleted phase, and separating the phenol precipitate phase and the phenol-depleted phase. The methods can further include extracting phenols from the separated phenol precipitate phase. The extracting can include mixing the separated phenol precipitate phase with an extraction solvent to solubilize in the extraction solvent at least a portion of the phenols originally present in the phenol precipitate phase.

First claim

What is claimed is:

1. A method of isolating phenols from a phenol-containing medium, the method comprising:
combining a phospholipid-containing composition with the phenol-containing medium to generate a combined medium;
incubating the combined medium to precipitate phenols in the combined medium and thereby form a phenol precipitate phase and a phenol-depleted phase;
separating the phenol precipitate phase and the phenol-depleted phase; and
extracting phenols from the separated phenol precipitate phase, wherein the extracting comprises mixing the separated phenol precipitate phase with an extraction solvent to solubilize in the extraction solvent at least a portion of the phenols originally present in the phenol precipitate phase.

2. The method of claim 1 , wherein the phospholipid-containing composition comprises negatively charged phospholipid.

3. The method of claim 1 , wherein the phospholipid-containing composition comprises phosphoinositide.

4. The method of claim 1 , wherein the phospholipid-containing composition comprises hydroxylated phospholipid.

5. The method of claim 1 , wherein the phospholipid-containing composition is or includes lecithin.

6. The method of claim 5 , wherein the lecithin comprises chemically modified lecithin.

7. The method of claim 5 , wherein the lecithin comprises hydroxylated lecithin.

8. The method of claim 1 , wherein the phospholipid-containing composition has a hydrophilic-lipophilic balance (HLB) greater than 3.

9. The method of claim 1 , wherein the phenol precipitate phase comprises a polyphenol.

10. The method of claim 1 , wherein the phenol precipitate phase comprises a flavonoid.

11. The method of claim 1 , wherein the phenol precipitate phase comprises an anthocyanin, an anthocyanidin, a proanthocyanidin, or a combination thereof.

12. The method of claim 1 , wherein total phenol mass concentration in the phenol-depleted phase is at least 30% less than total phenol mass concentration in the phenol-containing medium.

13. The method of claim 1 , wherein the incubating is performed at a temperature of about 0-17° C.

14. The method of claim 1 , wherein the phenol-containing medium comprises alcohol.

15. The method of claim 1 , further comprising combining pectin with the phospholipid-containing composition and the phenol-containing medium to generate the combined medium.

16. The method of claim 1 , wherein the extraction solvent comprises an organic solvent.

17. The method of claim 1 , wherein the extraction solvent comprises at least one of an alcohol and acetone.

18. The method of claim 1 , wherein the extraction solvent comprises water in an amount less than 20% v/v.

19. The method of claim 1 , wherein the separated phenol precipitate phase comprises the phenols and phospholipid and the mixing the separated phenol precipitate phase with the extraction solvent preferentially solubilizes the phenols over the phospholipid in the extraction solvent.

20. The method of claim 1 , wherein:
the phospholipid-containing composition comprises negatively charged phospholipid;
the phospholipid-containing composition has a hydrophilic-lipophilic balance (HLB) greater than 3;
total phenol mass concentration in the phenol-depleted phase is at least 30% less than total phenol mass concentration in the phenol-containing medium;
the extraction solvent comprises an alcohol and acetone;
the separated phenol precipitate phase comprises the phenols and phospholipid and the mixing the separated phenol precipitate phase with the extraction solvent preferentially solubilizes the phenols over the phospholipid in the extraction solvent.

Assignees

• Wisconsin Alumni Res Found

Inventors

• Bolling Bradley
• Wu Yuwei
• Voss Danielle
• Dorris Matthew

Classifications

• B01D11/0265

  Applying ultrasound · CPC title

• C07C37/004

  by obtaining phenols from plant material or from animal material · CPC title

• B01D9/0054

  Use of anti-solvent · CPC title

• B01D9/0004

  cooling by heat exchange (by evaporation of components of the mixture to be separated B01D9/0013; refrigeration machines F25B) · CPC title

• C07D311/30

  not hydrogenated in the hetero ring, e.g. flavones · CPC title