Synthesis of saturated, unsaturated, spin-labeled, and fluorescent cholesteryl esters: Acylation of cholesterol using fatty acid anhydride and 4-pyrrolidinopyridine.

ABSTRACT

A rapid, high yield method for the preparation of cholesteryl esters is described. The method is a modification of the catalytic procedure previously applied to the acylation of sn-glycero-3-phosphoryl-choline (Patel, K.M., J.D. Morrisett, and J.T. Sparrow, J. Lipid Res., 20676 (1979). Cholesteryl esters are formed in excellent yield by acylating cholesterol with fatty acid anhydride or fatty acid and dicyclohexylcarbodiimide in methylene chloride containing 4-pyrrolidinopyridine. The versatility of the method is demonstrated by the preparation of the cholesteryl esters of saturated, unsaturated, spinlabeled, and labile fluorescent fatty acids.