Paper on Methodology

Synthesis of 9-oxononanoyl cholesterol by ozonization

Correspondence to: Martin Mittelbach.

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 cholesterol 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.

Supplementary key words: cholesteryl ester, core aldehyde, ozonolysis, synthesis, lipid peroxidation

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