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Updated: Aug 3, 2026
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Synthesis of 9-oxononanoyl cholesterol by ozonization
H Boechzelt1, B Karten, P M Abuja
1Institute of Organic Chemistry, SFB Biomembranes Research Centre, Karl-Franzens-University, Graz, Austria.
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 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.
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