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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.
Mahadevan et al. (Mon,) studied this question.