The ozonation of cholesterol: Separation and identification of 2,4-dinitrophenulhydrazine derivatization products of 3β-hydroxy-5-oxo-5,6-secocholestan-6-al

Article abstract of DOI:10.1016/0039-128X(93)90023-G

The ozonation products of cholesterol, which are of interest as possible biomarkers of O₃ exposure, were studies by derivation with 2,4-dinitrophenylhydrazine (DNPH). The DNPH derivatization of 3&x03B2;-hydroxy-5-oxo-5,6-secocholesterol-6-al (2) produces the expected trans (3b) and cis (3c) derivatives of 3x03B2;-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), ¹³C 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 #s#x00A3;3af functionality is proposed for the formation of 3a. The ratio of sed3a/3b + 3c depends on the concentration of acid used and the reaction tiome. (Steroids 58: 225-229, 7993).