Method for producing eicosapentaenoic acid alkyl ester-containing composition

A technology of eicosapentaenoic acid alkyl ester and manufacturing method, which is applied in the fields of medical preparations containing active ingredients, fatty acid preparation/refining, food science, etc., and can solve problems such as difficult purification of EPA, and achieve low ratio and high content little effect

Pending Publication Date: 2021-10-29
NISSHIN PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the methods described in Patent Documents 1 to 5, when treating with an aqueous solution containing a silver salt, PUFA other than EPA also forms a complex with the silver salt, so it is difficult to purify EPA selectively.

Method used

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  • Method for producing eicosapentaenoic acid alkyl ester-containing composition
  • Method for producing eicosapentaenoic acid alkyl ester-containing composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0073] Hereinafter, examples are given to illustrate the present invention in more detail, but the present invention is not limited to these examples.

reference example 1

[0074] (Reference Example 1) Analysis of Fatty Acid Composition Ratio

[0075] 12.5 mg of the measurement sample was diluted in 1 mL of n-hexane, and the content ratio of each fatty acid in the total fatty acids was analyzed under the following conditions using a gas chromatography analyzer (Type 7890GC; manufactured by Agilent Technologies). The results are shown in mass % converted from the area of ​​the chromatogram.

[0076]

[0077] Injection port temperature: 250°C, split ratio: 10.

[0078]

[0079] Column: DB-WAX 0.25mm×30m manufactured by J&W;

[0080] Column temperature: 210°C;

[0081] He flow: 1.0mL / min, He pressure: 20 PSI.

[0082]

[0083] h 2 Flow: 40mL / min, air flow: 450mL / min;

[0084] He flow rate: 1.00 mL / min, DET temperature: 260°C.

[0085] The fatty acids analyzed were as follows. EPA-E: Eicosapentaenoic acid ethyl ester, DHA-E: Docosahexaenoic acid ethyl ester, AA-E: Arachidonic acid ethyl ester, ETA-E: Eicosatraenoic acid ethyl ester .

...

Embodiment 1

[0092] Thoroughly stir and mix 30g of raw material oil 1 and 14mL of cyclohexane to dissolve it. 41 g of the obtained solution and 150 g of a silver salt solution (50 mass % silver nitrate aqueous solution) were put into the flask, and it stirred at 300 rpm at 20 degreeC for 20 minutes in nitrogen atmosphere (oxygen concentration 0.4%). The liquid after stirring was left still at 20° C. for 15 minutes, and the separated organic layer and aqueous layer (silver salt solution containing PUFA-silver complex) were collected respectively. Add 150g of newly prepared silver salt solution to the recovered organic layer, stir at a speed of 300rpm at 20°C for 20 minutes under a nitrogen environment (oxygen concentration 0.4%), and leave the stirred liquid for 15 minutes at 20°C. minute. Recover the separated water layer, add 15mL hexamethylene therein, stir 20 minutes with the speed of 300rpm at 20 ℃, the liquid after stirring is left standstill at 20 ℃ for 15 minutes, reclaim the separ...

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Abstract

In order to provide a method for producing high-purity EPA, the present invention provides a method for producing an EPA alkyl ester-containing composition which contains 96 mass% or more of an EPA alkyl ester in the total fatty acid content thereof, and in which the trans isomer ratio in the EPA alkyl ester is 1.5 mass% or less. This method includes: (1) preparing a raw material oil containing 50-92 mass% of an EPA alkyl ester in the total fatty acid content thereof; (2) bringing the raw material oil and an aqueous solution including a silver salt into contact, the mass ratio of a DHA alkyl ester with respect to the EPA alkyl ester contained in the raw material oil being 3.3 mass% or less, and the trans isomer ratio in the EPA alkyl ester contained in the raw material oil being 2 mass% or less; (3) recovering the aqueous solution including a silver salt brought into contact with the raw material oil; (4) bringing the recovered aqueous solution including the silver salt into contact with an organic solvent; and (5) recovering the organic solvent brought into contact with the aqueous solution including a silver salt.

Description

technical field [0001] The present invention relates to a method for producing a composition containing an alkyl eicosapentaenoate. Background technique [0002] Eicosapentaenoic acid (EPA), which is one of highly unsaturated fatty acids (PUFA), has been clarified in recent years in its pharmacological effects, and is used as a raw material for medicines and health foods. The EPA requires high purity and no impurities as much as possible for raw materials used as pharmaceuticals or food. However, since PUFA such as EPA has many double bonds, it is not easy to obtain by chemical synthesis. Most of industrially used EPA is produced by extraction (extraction) or purification from raw materials derived from marine organisms rich in EPA, such as fish oil. However, since the biologically derived oil and fat raw material is a mixture of various fatty acids having different carbon numbers, double bond numbers or positions, and stereoisomer composition ratios, the target EPA conten...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11B7/00C11C1/00A23L33/12A61K31/232
CPCC11B7/00A23L33/115C11C1/007C11C1/02
Inventor 池本裕之野出纯一竹本健二
Owner NISSHIN PHARMA INC
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