Process for the isolation of hydroxy fatty acid derivatives from convolvulaceae plants

• US 5,296,621 A
• Filed: 12/14/1992
• Issued: 03/22/1994
• Est. Priority Date: 07/20/1989
• Status: Expired due to Fees

• Current Assignee: Unilever Patent Holdings BV (Unilever PLC)
• Original Assignee: Unilever Patent Holdings BV (Unilever PLC)
• Inventors: Bakker, Jan, Roos, Robert
• Primary Examiner(s): Dees, Jose G.
• Assistant Examiner(s): CARR, DEBORAH D
• Application Number:
  US07/990,935
• Time in Patent Office: 463 Days
• Field of Search: 554/15, 424/195.1
• US Class Current: 554/15
• CPC Class Codes: C07C 51/09 from carboxylic acid esters or lactones
• CPC Class Codes: C07C 59/01 Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
• CPC Class Codes: C07C 59/105 having five or more carbon atoms, e.g. aldonic acids
• CPC Class Codes: C11B 1/10 by extracting
• CPC Class Codes: C11C 1/04 by hydrolysis

Abstract

The invention provides a process for the isolation of hydroxy fatty acid derivatives from Convolvulaceae plants like Ipomoea batatas and Ipomoea orizabensis by extracting parts of said plants like leaves, stems, seeds and in particular roots and tubers thereof, with an organic solvent, removing the solvent for at least the main part from the extract, dispersing the obtained residue into water, subjecting the obtained dispersion to a single hydrolysis step and recovering the released hydroxy fatty acids, like 11-hydroxy palmitic acid and 3,11-hydroxy myristic acid from the aqueous dispersion by means of an extraction agent. The obtained hydroxy fatty acid may be used in the synthesis of specific organic compounds like lactones or in the preparation of products having purgative properties and of thickeners for lubricating greases respectively.

Claims

1. In a process for the isolation of a hydroxy fatty acid or alkyl ester thereof from Convolvulaceae plants by extracting parts of said plants with an extraction agent and subsequently subjecting the extraction liquor to hydrolysis, the improvement which comprises:

(a) extracting the parts of the Convolvulaceae plants with an organic solvent;

(b) removing the solvent from at least the main part from the extract to obtain a resinous material containing the desired hydroxy fatty acid in ester form, dispersing the thus obtained material into water and subjecting the obtained dispersion to hydrolysis to form the hydroxy fatty acid or alkyl ester, said hydrolysis selected from the group consisting of;

(i) acid hydrolysis performed at a temperature in the range of 25°

to 180°

C. and under a pressure of from 1 up to 25 bar;

(ii) a neutral hydrolysis performed at a pH of about 7 at a temperature in the range of 25°

to 180° and

under a pressure of from 1 up to 25 bar; and

(iii) an enzymatic hydrolysis in the presence of an enzyme having ester activity performed in a pH range of 4-9 at a temperature in the range of 25°

to 40°

C. under about atmospheric pressure; and

c) recovering the resulting hydroxy fatty acid or alkyl ester thereof from the aqueous suspension.

2. Process according to claim 1, wherein species of the genus Ipomoeeae are used as the Convolvulaceae-plants.

3. Process according to claim 1, wherein there are used in stage (a) sliced roots of Ipomoea orizabensis or sliced tubers of Ipomoea batatas (sweet potato), Ipomoea turpethum, Ipomoea operaculata and/or Convolvulus microphyllus.

4. Process according to claim 3, wherein there are used in stage (a) sliced roots of Ipomoea orizabensis or sliced tubers of Ipomoea batatas.

5. Process according to claim 1, wherein there is used in stage (a) a "food grade" solvent as extraction agent.

6. Process according to claim 5, wherein there is used in stage (a) methylacetate as the "food grade" solvent.

7. Process according to claim 1, wherein the hydrolysis is neutral hydrolysis performed at a pH of about 7, at a temperature in the range of from 135°

to 145°

C. and under a pressure of from 3 to 10 bar.

8. Process according to claim 1 wherein the hydrolysis is an acid hydrolysis performed with the help of hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, citric acid or tartaric acid or mixtures thereof at a temperature in the range of 100°

to 180°

C. under a pressure of from about 1 up to 25 bar.

9. Process according to claim 8, wherein the acid hydrolysis step is performed with hydrochloric acid at a temperature in the range of 100°

-120°

C. and under a pressure of from 1 to 5 Bar.

10. Process according to claim 1, wherein the hydrolysis step is performed in a pH-range of 7-9 and at a temperature in the range of 25°

to 40°

C. with the help of an enzyme having esterase activity.

11. Process according to claim 10, wherein a lipase is used as the enzyme having esterase activity.

12. Process according to claim 1, wherein stage (c) hexane or cyclohexane is used as extraction agent.

13. Process according to claim 1, wherein the hydroxy fatty acid derivative(s) are recovered in stage (c) by means of a distillation under reduced pressure and at elevated temperature.

14. A process according to claim 1 wherein the plants are Radix Scammoniae Mexicanae plants and the acid obtained is 11-hydroxy palmitic acid.

15. The process of claim 14 wherein the hydrolysis is performed according to (i) in the presence of aqueous ethanol and the desired acid is obtained as the ethyl ester thereof.