Steroids p. 225 - 229 (1993)
Update date:2022-08-25
Topics:
Wang, Keyang
Bermudez, Eliezer
Pryor, William A.
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).
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