Process for obtaining 3′-epilutein

• US 6,420,614 B1
• Filed: 10/10/2000
• Issued: 07/16/2002
• Est. Priority Date: 10/10/2000
• Status: Expired due to Fees

• Current Assignee: Industrial Organica, S.A. De C.V.
• Original Assignee: Industrial Organica, S.A. De C.V.
• Inventors: Eugster, Conrad Hans, Torres-Quiroga, José-Odon, Montoya-Olvera, Ricardo
• Primary Examiner(s): Shippen, Michael L.
• Application Number:
  US09/685,321
• Time in Patent Office: 644 Days
• Field of Search: 568/824, 568/816
• US Class Current: 568/816
• CPC Class Codes: C07C 403/24 having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene

Abstract

A process for obtaining 3′-epilutein, by epimerization of a lutein-containing extract with an aqueous solution of a strong organic acid which is slowly added under agitation at room temperature, in the presence of an organic aprotic media, to obtain 3′-epilutein(crystals) in a solution which is neutralized with an alkali and extracting the 3′-epilutein from said solution by means of an organic media, then washing and drying the crystals and purifying them by chromatography by means of a chromatography column.

Claims

1. A process for obtaining 3′

-epilutein, comprising;

reacting a lutein-containing extract with an aqueous inorganic or organic acid whose anions possess a very low nucleophilicity in the presence of an organic aprotic media, to obtain a 3′

-epilutein solution.

2. The process according to claim 1, wherein the inorganic or organic acid is a strong mineral or organic acid, selected from the group consisting of sulfuric acid, hydrochloric acid, trifluoroacetic acid, perchloric acid, tetrafluoroboric acid, or mixtures thereof.

3. The process according to claim 1, comprising slowly adding the strong inorganic or organic acid under agitation at a temperature between ambient temperature and about 50°

C.

4. The process according to claim 1, wherein the organic aprotic media is selected from tetrahydrofurane, hexane, dimethylformamide, dimethylsulfoxide, glycolethers, or mixtures thereof.

5. The process according to claim 1, comprising neutralizing the solution with an alkali.

6. The process according to claim 1 comprising neutralizing the solution with ammonium hydroxide.

7. The process according to claim 1, comprising partitioning a 3′

-epilutein solution by means of an organic media.

8. The process according to claim 1, comprising partitioning the 3′

-epilutein solution with an organic solvent.

9. The process according to claim 1, comprising partitioning the 3′

-epilutein solution with methylene dichloride.

10. The process according to claim 1, comprising washing the 3′

-epilutein solution.

11. The process according to claim 1, comprising washing the 3′

-epilutein solution with water.

12. The process according to claim 1, comprising washing the 3′

-epilutein solution with a solution of sodium chloride.

13. The process according to claim 1, comprising drying the 3′

-epilutein solution with anhydrous sodium sulfate.

14. The process according to claim 1, comprising crystallizing the 3′

-epilutein by solvent evaporation to obtain 3′

-epilutein crystals.

15. The process according to claim 1, comprising purifying the 3′

-epilutein crystals by chromatography.

16. The process according to claim 1, comprising purifying the 3′

-epilutein crystals by chromatography in a column of silica gel.

17. The process according to claim 1, wherein the reaction time is from about 4 hours to about 130 hours.

18. The process according to claim 1, comprising reacting an extract containing about 1% to about 99.22% by weight of lutein with 1N sulfuric acid, in a ratio of about 1:

1 to about 1;

8.

25. The process according to claim 14, comprising purifying the 3′

-epilutein crystals by chromatography.

26. The process according to claim 14, comprising the 3′

-epilutein crystals by chromatography in a column of silica gel.

19. A process for obtaining 3′

-epilutein, comprising;

reacting a lutein-containing extract with an aqueous solution of sulfuric acid, in the presence of tetrahydrofurane, to obtain a solution of 3′

-epilutein;

neutralizing the solution with ammonium hydroxide;

partitioning the 3′

-epilutein by means of dichloromethane;

washing the 3′

-epilutein solution with water and with a solution of sodium chloride;

drying the 3′

-epilutein solution by means of anhydrous sodium sulfate;

crystallizing the 3′

-epilutein by evaporation, to obtain 3′

-epilutein crystals; and

purifying the 3′

-epilutein crystals by chromatography in a column of silica gel.

20. The process according to claim 19, wherein the lutein containing extract is reacted with an aqueous solution of sulfuric acid, by slowly adding the sulfuric acid under agitation, at a temperature between the ambient temperature and about 50°

C., during a period of from about 4 hours to about 130 hours.

21. The process according to claim 19, comprising reacting the extract containing about 1% to about 99.22% by weight of lutein with 1N sulfuric acid, in a ratio of about 1:

1 to about 1;

8.

22. A process for obtaining optically active (3R,3′

R)-zeaxanthin, comprising;

reacting a lutein-containing extract with an aqueous solution of an inorganic or organic acid in the presence of an organic aprotic media, to obtain a 3′

-epilutein solution;

neutralizing the solution with an alkali; and

reacting 3′

-epilutein crystals, with a strongly alkaline aqueous solution.

23. A process for obtaining optically active (3R,3′

R)-zeaxanthin, according to claim 22, wherein the inorganic or organic acid is a strong mineral or organic acid, selected from the group consisting of sulfuric acid, hydrochloric acid, trifluoroacetic acid, perchloric acid, tetrafluoroboric acid, or mixtures thereof.

24. A process for obtaining optically active (3R,3′

R)-zeaxanthin, according to claim 22, wherein the organic aprotic media is selected from tetrahydrofurane, hexane, dimethylformamide, dimethylsulfoxide, glycolethers, or mixtures thereof.