Abstract
The ozonation products of cholesterol, which are of interest as possible biomarkers of O 3 exposure, were studies by derivation with 2,4-dinitrophenylhydrazine (DNPH). The DNPH derivatization of 3β-hydroxy-5-oxo-5,6-secocholesterol-6-al (2) produces the expected trans (3b) and cis (3c) derivatives of 3β-hydroxy-5-oxo-5,6-secocholestan-6-al,a nd the unexpected DNPH derivatives of 3,5-hydroxy-B-norcholestane-6-carboxyaldehyde (3a). The structures of 3a, 3b, and 3c were identified with 1H nuclear magnetic resonance (NMR), 13 C NMR, DEPT, COSY,a nd H-C correlation two-dimensional NMR techniques, and by comparison with the spectra of known compounds. A possible involving an enamine functionality is proposed for the formation of 3a. The ratio of sol3a (3b + 3c) depends on the concentration of acid used and the reaction tiome. (Steroids 58: 225–229, 1993)
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