Synthesis of 9-oxononanoyl cholesterol by ozonization1

Abstract

A new route for the preparation of 9-oxononanoyl cholesterol (5) and its stable dimethylacetal (4) is described. The core aldehyde 5 is one of the major products formed during lipid peroxidation. The synthesis starts with the ozonization of oleic acid in methanol and further reduction with dimethyl sulfide to yield 9,9-dimethoxy nonanoic acid (2a). The condensation of 2a with cholester ol is achieved with N,N′-dicyclohexylcarbodiimide in dichloromethane to give 4. Further hydrolysis of 4 with the help of an acidic ion exchange resin yields 9-oxononanoyl cholesterol.—Boechzelt, H., B. Karten, P. M. Abuja, W. Sattler, and M. Mittelbach. Synthesis of 9-oxononanoyl cholesterol by ozonization. J. Lipid Res. 1998. 39: 1503–1507.

Keywords

• cholesteryl ester
• core aldehyde
• ozonolysis
• synthesis
• lipid peroxidation