Synthesis of 9-oxononanoyl cholesterol by ozonization.
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
H
Institute of Organic Chemistry, SFB Biomembranes Research Centre, Karl-Franzens-University, Graz, Austria.
Karten
B
B
Abuja
P M
PM
Sattler
W
W
Mittelbach
M
M
D002784:Cholesterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D015227:Lipid Peroxidation; D000432:Methanol; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D019301:Oleic Acid; D010126:Ozone
C114702:9-oxononanoyl cholesterol; D007202:Indicators and Reagents; D019301:Oleic Acid; D010126:Ozone; D002784:Cholesterol; D000432:Methanol