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

• Published in: Steroids Vol. 58; no. 5; pp. 225 - 229
• Main Authors: Wang, Keyang, Bermúdez, Eliezer, Pryor, William A.
• Format: Journal Article
• Language: English
• Published: Elsevier Inc 1993
• Subjects: 3β-hydroxy-5,6-secocholestan-6-al; cholesterol; DNPH derivatization; enamine functionality; ozonationl; sterol; cholesterol; 3β-hydroxy-5,6-secocholestan-6-al; sterol; enamine functionality; ozonationl; DNPH derivatization
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/0039-128X(93)90023-G

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)