Processes for chromatographic fractionation of fatty acids and t

Details Processes for chromatographic fractionation of fatty acids and t Processes for chromatographic fractionation of fatty acids and t

1996-01-18

1998-02-17

Shaver, Paul F.

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

Organic compounds

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

554205, C11B 310

Patent

active

057193029

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention concerns processes for chromatographic fractionation of compositions comprising polyunsaturated fatty acids or derivatives thereof.
2. Description of the Related Art
Fractionation of fatty acids or their derivatives has been widely investigated in recent years. The reason for this interest lies in the recognition that some fatty acids, especially long chain polyunsaturated fatty acids, are precursors for so-called prostanoid compounds, including prostacyclins and prostaglandins, which play an important role in the regulation of biological functions such as platelet aggregation, inflammation and immunological responses.
In this specification polyunsaturated fatty acids are identified according to the system wherein the omega- or n-number denominates the position of the first double bond when counting from the terminal methyl group, e.g in an omega-3 or n-3 fatty acid, the first double bond occurs at the third carbon atom from the terminal methyl group of the acid. Further, when a fatty acid is identified, for instance, as C18:3, this refers to a fatty acid having 18 carbon atoms in the chain and three double bonds.
Two important polyunsaturated omega-3 fatty acids, EPA (eicosapentaenoic acid, C20:5) and DHA (docosahexaenoic acid, C22:6) are found in marine oils. The biological properties of these fatty acids have been discussed in many publications and patents, such as for instance GB-2221843 which teaches that concentrated mixtures of EPA and DHA are efficient products for the treatment and prophylaxis of multiple risk factors for cardio-vascular diseases.
Correspondingly, the polyunsaturated fatty acids of the omega-6 series, such as gamma-linolenic acid or arachidonic acid, may be produced from linseed oil or corn oil for nutritional and pharmaceutical uses.
In order to be active without toxicity, these. polyunsaturated compounds must exhibit an all-cis (Z--Z) conformation corresponding to how they appear in nature. Unfortunately, polyunsaturated fatty acids are extremely fragile when heated in the presence of oxygen as they are subjected to fast isomerization, peroxidation and oligomerization. Thus the fractionation and purification of these products to prepare the pure fatty acids is extremely difficult: distillation--even under vacuum--leads to non-acceptable product degradation; whereas liquid-liquid extraction or crystallization are not efficient, especially not when high purity products for nutritional or pharmaceutical uses are required.
Polyunsaturated fatty acids are to be found in natural raw materials, such as marine oils or vegetable oils. In such oils, and in concentrates of polyunsaturated fatty acids from such oils, there are many possible categories of by-products/contaminants that preferably should be removed in products intended for nutritional and pharmaceutical uses. A discussion of the major categories of such unwanted by-products/contaminants is given by H. Breivik and K. H. Dahl, Production and Quality Control of n-3 Fatty acids. In: J. C. Frolich and C. von Schacky, Klinische Pharmakologie. Clinical Pharmacology Vol. 5 Fish, Fish Oil and Human Health 1992 W. Zuckschwerdt Verlag, Munich.
Thus the fatty acids do not naturally occur in simple binary mixtures from which they can be easily isolated.
To illustrate the difficulty of achieving pure polyunsaturated fatty acids by fractionation of natural oils, Tables 1 and 2 below present the composition of some typical fatty acid ethyl ester mixtures obtained from natural sources either by a simple ethanol transesterification or with subsequent fractionation of unsaturated fatty acid chains through molecular distillation.


TABLE 1 ______________________________________ Composition of fatty acids esters obtained from a typical linseed oil (transesterification) in mass percent ______________________________________ C16:0 5.3 C18:0 2.5 C18:1 14.5 C18:2 16.8 C18:3 (n-3) 60.6 (.alpha.-linolenic acid) Others 0.3 ____________________________________

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