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Journal of Lipid Research, Vol. 3, 106-110, January 1962
Copyright © 1962 by Lipid Research, Inc.

Preparation of cholesterol esters of long-chain fatty acids and characterization of cholesteryl arachidonate

V. Mahadevan and W. O. Lundberg

University of Minnesota, The Hormel Institute, Austin, Minnesota

Cholesterol esters of long-chain saturated fatty acids (C₁₂ to C₂₂), as well as those of the C₁₈ unsaturated fatty acids (oleic, linoleic, and linolenic), were prepared by the ester interchange method, starting with cholesteryl acetate and the methyl esters of the fatty acids and using sodium ethylate as a catalyst. Cholesteryl arachidonate was synthesized and obtained in crystalline form, and its melting point, optical rotation, and infrared spectrum were recorded. The infrared spectrum of cholesteryl arachidonate showed minor variations from the unsaturated esters of the C₁₈ acids. However, the infrared spectra of cholesteryl arachidonate prepared from arachidonate of different sources, one synthetic and the other of natural origin, were identical in all respects. The application of this procedure to the synthesis of labeled cholesterol esters on a microscale was demonstrated by the preparation of cholesteryl oleate-C¹⁴ from randomly labeled C¹⁴-methyl oleate. The purity of the cholesterol esters was established by thin-layer chromatography and other techniques.

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