IP Library Granted Patent US 8,420,349
Granted Patent B2
US 8,420,349 · App. 12/668,533 · Granted Apr 16, 2013

Enzymatic modification of oil

Inventors: Jaroslav A. Kralovec (Halifax, CA); Weijie Wang (Dartmouth, CA); Colin James Barrow (Torquay, AU)
Assignee: Ocean Nutrition Canada Limited
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,420,349
App. No.
12/668,533
Granted
Apr 16, 2013
Kind
B2
Abstract

The disclosed subject matter relates generally to a method for modifying oil, and specifically to a process for increasing the concentration of polyunsaturated fatty acid in an oil composition.

Claims (19)

1. A method for modifying an oil comprising a glyceride, comprising: a) contacting the oil with an aqueous solution of Thermomyces lanuginosus lipase at a time and temperature sufficient to hydrolyze at least a portion of the glyceride and thereby provide a composition comprising a free saturated fatty acid fraction and a hydrolyzed glyceride fraction; b) separating at least a portion of the free saturated fatty acid fraction from the hydrolyzed glyceride fraction; and c) esterifying, in the presence of a second lipase, the hydrolyzed glyceride fraction from step b) with a polyunsaturated fatty acid or ethyl ester thereof.

2. The method of claim 1 , wherein the oil comprises at least one diglyceride or triglyceride.

3. The method of claim 1 , wherein the oil is contacted with a buffer solution of about pH 10 prior to the contacting step a).

4. The method of claim 1 , further comprising after the contacting step a) and prior to the separating step b), sealing the oil composition and Thermomyces lanuginosus lipase in an inert or substantially inert atmosphere.

5. The method of claim 1 , wherein the Thermomyces lanuginosus lipase is in the form of a phosphate buffered solution of pH about 7.2.

6. The method of claim 1 , wherein the Thermomyces lanuginosus lipase is immobilized on a matrix, wherein the matrix comprises a copolymer of (i) divinylbenzene and (ii) acrylic acid, methacrylic acid, methylacrylate, methylmethacrylate, ethylvinylbenzene or styrene, wherein the copolymer comprises at least 79 weight % divinylbenzene and 4 weight % or less non-polymerizable impurities.

7. The method of claim 1 , wherein the Thermomyces lanuginosus lipase is used in an amount of from about 0.0001 to about 5% by weight of the total oil composition.

8. The method of claim 1 , wherein in step b) the saturated fatty acid fraction is separated from the hydrolyzed glyceride fraction by molecular distillation.

9. The method of claim 1 , wherein in step b) the saturated fatty acid fraction is separated from the hydrolyzed glyceride fraction by short path molecular distillation.

10. The method of claim 1 , wherein in step b) the saturated fatty acid fraction is separated from the hydrolyzed glyceride fraction by wiped film evaporation.

11. The method of claim 1 , wherein the second lipase comprises Candida antarctica lipase B.

12. The method of claim 1 , wherein step c), esterifying in the presence of a second lipase, is under anhydrous conditions.

13. The method of claim 1 , wherein the second lipase is immobilized on a matrix, wherein the matrix comprises a copolymer of (i) divinylbenzene and (ii) acrylic acid, methacrylic acid, methylacrylate, methylmethacrylate, ethylvinylbenzene or styrene, wherein the copolymer comprises at least 79 weight % divinylbenzene and 4 weight % or less non-polymerizable impurities.

14. The method of claim 1 , wherein the second lipase is present in an amount of from about 0.1% to about 20% by weight of total weight of the polyunsaturated fatty acid or ethyl ester thereof and hydrolyzed glyceride.

15. The method of claim 1 , wherein the polyunsaturated fatty acid or ethyl ester thereof comprises one or more of eicosapentaenoic acid, docosahexaneoic acid, or docosapentaenoic acid.

16. The method of claim 1 , wherein the oil composition comprises a microbial oil, plant oil, animal oil, marine oil, algal oil, or combination thereof.

17. The method of claim 1 , wherein the oil comprises fish oil.

18. The method of claim 1 , wherein the oil comprises a crude oil, a semi-refined oil, a refined oil, or a re-esterified oil.

19. The method of claim 1 , wherein the glyceride, after step c), comprises a higher concentration of polyunsaturated fatty acid than the oil composition.

Assignments (2)
NUNC PRO TUNC ASSIGNMENT Recorded Sep 19, 2013
From: OCEAN NUTRITION CANADA LIMITED
To: DSM NUTRITIONAL PRODUCTS AG
Reel/Frame 031246/0134 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2010
From: KRALOVEC, JAROSLAV A.; WANG, WEIJIE; BARROW, COLIN JAMES
To: OCEAN NUTRITION CANADA LIMITED
Reel/Frame 024609/0822 →
Continuity (2)
Provisional Application 60959248 · Jul 12, 2007
Related Publication 20110045555A1 · Feb 24, 2011