Composition containing eicosapentaenoic acid alkyl ester, and method for producing same

Patent metadata

Field	Value
Publication number	US-11648229-B2
Application number	US-202017076090-A
Country	US
Kind code	B2
Filing date	Oct 21, 2020
Priority date	Sep 17, 2014
Publication date	May 16, 2023
Grant date	May 16, 2023

Abstract

Provided are: a composition containing 96-99 area % of eicosapentaenoic acid alkyl ester, the composition having an arachidonic acid alkyl ester content of 0.7 area % or less, and an eicosapentaenoic-acid-alkyl-ester mono-trans isomer content of 2.5 area % or less; and a method for producing a composition containing a high concentration of eicosapentaenoic acid alkyl ester, the method including performing precision distillation on a composition containing eicosapentaenoic acid alkyl ester, obtained by alkyl esterification of a raw material oil containing eicosapentaenoic acid, under a vacuum of 0.2 Torr or lower and a temperature of 190° C. or lower in the entire column, and performing a concentration treatment on the precision-distilled composition using chromatography.

First claim

The invention claimed is:

1. An eicosapentaenoic acid alkyl ester-containing composition which, upon measurement by gas chromatography under the following analytical conditions, comprises 96-98 area % of an eicosapentaenoic acid alkyl ester, wherein the sum of the contents of substances whose relative retention times appear as peaks at about 1.077, with the mean retention time of ethyl eicosapentaenoate being taken as 1, is 2.5 area % or less, and wherein a feed oil of the composition is an oil or fat derived from a marine product as a feed:
[gas chromatographic analysis conditions: GC-FID measurement conditions]
GC: 6890N (Agilent Technologies)
Column: DB-WAX (Agilent Technologies)
30 m×0.25 mm ID, 0.25 μm in film thickness

Carrier gas: helium, 0.5 mL/min
Injection port: 300° C., 1 μL, Split (1:100)
Column temperature: 200° C. (constant)
Detector: FID, 300° C.
Makeup gas: nitrogen, 40 mL/min.

2. The composition of claim 1 , wherein the content of an arachidonic acid alkyl ester is 0.7 area % or less.

3. The composition of claim 1 , wherein the content of the arachidonic acid alkyl ester is 0.1 area % or less.

4. The composition of claim 1 , wherein the content of an eicosatetraenoic acid alkyl ester is 0.7 area % or less.

5. The composition of claim 1 , wherein the content of an octadecatetraenoic acid alkyl ester is 0.4 area % or less.

6. The composition of claim 1 , wherein the content of a nonadecapentaenoic acid alkyl ester is 0.2 area % or less.

7. The composition of claim 1 , wherein the eicosapentaenoic acid alkyl ester is ethyl eicosapentaenoate or methyl eicosapentaenoate.

8. The composition of claim 1 , wherein the content of a n-nonadecanoic acid (C19:0) alkyl ester is 0.1 area % or less.

9. The composition of claim 1 , wherein the content of an arachidic acid (C20:0) alkyl ester is 0.2 area % or less.

10. The composition of claim 1 , wherein the content of alkyl esters of saturated fatty acids is 0.5 area % or less.

11. The composition of claim 1 , wherein the content of an icosa-5,9,11,14,17-pentaenoic acid (C20:5n-3(5,9,11,14,17)) alkyl ester is 0.2 area % or less.

12. The composition of claim 1 , wherein the content of a henicosapentaenoic acid alkyl ester is 0.2 area % or less.

13. The composition of claim 1 , wherein the content of a dihomo-γ-linolenic acid alkyl ester is 0.05 area % or less.

14. The composition of claim 1 , wherein the content of alkyl esters of monounsaturated fatty acids with carbon number of 20 or more is 0.05 area % or less.

15. A pharmaceutical composition comprising the eicosapentaenoic acid alkyl ester-containing composition of claim 1 as an effective component.

16. The pharmaceutical composition of claim 15 further comprising a pharmaceutically acceptable additive component.

Assignees

• Nippon Suisan Kaisha Ltd
• Mochida Pharm Co Ltd

Inventors

• Doisaki Nobushige
• Arato Shingo
• Fukae Takuro

Classifications

• A61P3/06

  Antihyperlipidemics · CPC title

• C11B3/12

  by distillation · CPC title

• C11C3/10

  Ester interchange · CPC title

• A61P7/02

  Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors · CPC title

• C07C67/54

  by distillation · CPC title