Method to produce highly pure eicosapentaenoic acid or its ester

Details Method to produce highly pure eicosapentaenoic acid or its ester Method to produce highly pure eicosapentaenoic acid or its ester

1994-06-27

1998-11-24

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554191, 554193, 202 41, 202 81, 202 82, 202 98, C11B 312

Patent

active

058409440

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP92/01393 filed Oct. 28, 1992.


TECHNICAL FIELD

The present invention relates to a method of producing highly pure eicosapentaenoic acids or their esters. More particularly, the present invention relates to a novel, highly efficient method of producing highly pure eicosapentaenoic acids (EPA) or their esters, which is a useful in the treatment and prevention of thrombotic diseases.


BACKGROUND TECHNOLOGY

It is well known for many years that eicosapentaenoic acids (EPA), their esters, amides and the like are useful for the prevention of thrombus and the treatment of thrombotic disease.
It is also well known that these eicosapentaenoic acids occur in natural and aquatic oils and fats, such as in mackerels, sardines, and cods, in particular, per se or as derivatives such as glycerides. Many published papers propose a method to separate eicosapentaenoic acids from these fish oils and the like.
Natural fats consisting of these fish oils, however, contain, in addition to eicosapentaenoic acids of carbon number 20 and double bond number 5, an overwhelmingly large quantity of diverse fatty acids with carbon numbers ranging from 12 to 24, and double bond numbers from 0 to 6. It is thus very difficult to effectively isolate and refine eicosapentaenoic acids as a pure product of a high concentration.
As one of the methods to isolate and refine eicosapentaenoic acids, a method to rectifying a mixture of fatty acids containing eicosapentaenoic acids and then refining them by forming urea adducts is known (publication of unexamined patent application Nos. 149400-1982 and 8037-1983). With this method, however, eicosapentaenoic acids are only insufficiently isolated from other C20 high level unsaturated fatty acids and intervening C18 and C22 high level unsaturated fatty acids, with the result that only 95% pure products are produced at best. In fact, the method disclosed in unexamined patent application No. 149400 indicates that a 93.5% purity is the highest achievable level in its working example 3. EPA recovery is also a very low 30%.
The use of reversed-phase partition type column chromatography is proposed as a means to partition-refine eicosapentaenoic acids (publication of unexamined patent application No. 88339-1983). With this method, however, in spite of using raw materials containing highly concentrated (30%) eicosapentaenoic acids, the same quantity of docosa-hexaenoic acids (DHA) are included in the final product, and these two are only incompletely separated, with the result that the yield of 95% pure eicosapentaenoic acids is only 40%.
It is thus very difficult with conventional methods to produce highly pure eicosapentaenoic acids, those of 95% purity and above in particular, from a mixture of fats with a high recovery rate.


DISCLOSURE OF THE PRESENT INVENTION

The present invention has been made in view of the above circumstances to provide a novel method, by eliminating the drawbacks of conventional methods, to produce highly pure eicosapentaenoic acids or their esters with a high recovery rate, which is also available for acquiring products which are 95% pure or above.
To solve the problems encountered in conventional methods, the present invention provides a method to produce highly pure eicosapentaenoic acids or their esters wherein a mixture of fatty acids or their ester produced from natural oils and fats containing eicosapentaenoic acids or their derivatives is precision distilled under a high vacuum using a plurality of distillation columns to derive a fraction mainly comprising fatty acids of carbon number 20 or their esters, which is then subjected to a reversed-phase partition type column chromatography for partition refinement.


BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the structure of a continuous distillation method used in the present invention.
FIG. 2 is the absorbency spectrum of a chromatography as a working example of the present invention.


DETAILED DESCRIPTION OF THE PRESENT INVENTION

The key points of the present invention are removal

REFERENCES:
patent: 5215630 (1993-06-01), Hata et al.

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