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Production and Purification of Esters of Polyunsaturated Fatty Acids

a technology of polyunsaturated fatty acids and esters, which is applied in the direction of fatty acid chemical modification, drug compositions, metabolic disorders, etc., can solve the problems of substantial levels of saturated fatty acids and other undesirable impurities, efforts directed to purify pufas, and suffer from problems

Inactive Publication Date: 2009-01-22
DSM IP ASSETS BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0034]In some embodiments, the medium further comprises an organic solvent that can solubilize the ester of the polyunsaturated fatty acid.

Problems solved by technology

The oils derived from each of these sources, however, also contain substantial levels of saturated fatty acids and other undesirable impurities.
Previous efforts directed to purifying PUFAs, however, have suffered from problems such as high costs and decreased yields due, in part, to the use of harsh reagents.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0161]This example illustrates a method of the present invention for purifying ethyl docosahexaneoate (DHA ethyl ester) from docosahexaneoic acid-containing single cell oil.

[0162]150 mL of absolute ethanol (EtOH) was added to 175 g (approximately 0.2 moles of triglyceride) of DHASCO®-T oil (Martek Biosciences Corporation, Columbia, Md., having a DHA content of 0.4 g / g oil) in a one-liter flask under nitrogen (N2) at room temperature. DHASCO®-T oil is prepared from the microalgae Crypthecodinium cohnii. The mixture was allowed to stir for 15 minutes to obtain a homogeneous solution. 67 g of a 21% solution of sodium ethoxide / ethanol (NaOEt / EtOH; approximately 1.04 molar equivalents of triglycerides) was then added to the solution and the mixture was allowed to reflux under N2 for about 9 hours. The progress of the reaction was monitored by gas chromatography (GC) and thin-layer chromatography (TLC). When the reaction was completed, approximately 75 mL of EtOH was removed by distillati...

example 2

[0164]This example illustrates a method of the present invention for purifying ethyl docosahexaneoate (DHA ethyl ester) from a crude Crypthecodinium cohnii oil.

[0165]A crude oil obtained from Crypthecodinium cohnii by hexane extraction (DHA content of 0.5 g / g oil) was used directly without any further processing, such as winterization and / or RBD processing. 150 mL of absolute ethanol was added to 175 g (approximately 0.2 moles of triglycerides) of the crude oil in a one-liter flask under N2 at room temperature. The mixture was allowed to stir for 15 minutes to obtain a homogeneous solution. 67 g of a 21% solution of NaOEt / EtOH (approximately 1.04 molar equivalents of triglycerides) was then added to the solution, and the mixture was allowed to reflux under N2 for about 10 hours. The progress of the reaction was monitored by GC and TLC. When the reaction was completed, approximately 75 mL of ethanol was removed by distillation, and the mixture was allowed to cool to room temperature ...

example 3

[0167]This example illustrates a method of the present invention for purifying ethyl docosahexaenoate (as a DHA ethyl ester / DPA ethyl ester mixture) from a crude Schizochytrium sp. oil.

[0168]A crude oil obtained from Schizochytrium sp. by hexane extraction was used directly without any further processing, such as winterization and / or RBD processing.

[0169]150 mL of absolute ethanol was added to 175 g (approximately 0.2 moles of triglycerides) of the crude oil (DHA content 40%, DPA content 15%) in a one-liter flask under N2 at room temperature. The mixture was allowed to stir for 15 minutes to obtain a homogeneous solution. 67 g of a 21% solution of NaOEt / EtOH (approximately 1.04 molar equivalents of triglycerides) was then added to the solution, and the mixture was allowed to reflux under N2 for about 10 hours. The progress of the reaction was monitored by GC and TLC. When the reaction was completed, approximately 65 mL of ethanol was removed by distillation, and the mixture was allo...

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Abstract

The present invention includes methods for producing and purifying esters of polyunsaturated fatty acids that include reacting a composition having triglycerides with polyunsaturated fatty acid residues in the presence of an alcohol and a base to produce an ester of a polyunsaturated fatty acid from the triglycerides. The composition can be a polyunsaturated fatty acid-containing composition that has not been conventionally processed. The reacted composition can be further processed by distillation.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]This application claims the benefit of priority under 35 U.S.C. § 119(e) of U.S. Provisional Application No. 60 / 947,284, filed Jun. 29, 2007, the disclosure of which is incorporated by reference herein in its entirety.FIELD OF THE INVENTION[0002]The invention relates to methods for producing and purifying esters of polyunsaturated fatty acids from triglyceride containing compositions. The invention also relates to compositions comprising polyunsaturated fatty acids.BACKGROUND OF THE INVENTION[0003]It is desirable to increase the dietary intake of many beneficial nutrients. Particularly beneficial nutrients include fatty acids such as omega-3 and omega-6 long chain polyunsaturated fatty acids (LC-PUFAs) and esters thereof. Omega-3 PUFAs are recognized as important dietary compounds for preventing arteriosclerosis and coronary heart disease, for alleviating inflammatory conditions and for retarding the growth of tumor cells. Omega-6 PUFAs se...

Claims

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Application Information

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IPC IPC(8): A61K31/23A61P25/28C11C1/00
CPCA21D2/16A23K1/164C07C67/03C07C67/08C11C3/003C07C69/587C07C67/60C07C69/533A23K20/158A23L33/12A61P25/28A61P3/06
Inventor RAMAN, KRISHNALEE, JUNGLEININGER, NEILLUIGART, CHRIS
Owner DSM IP ASSETS BV
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