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

Journal Article · Sat May 01 04:00:00 EDT 1993 · Steroids; (United States)

DOI:https://doi.org/10.1016/0039-128X(93)90023-G· OSTI ID:6146650

Wang, K; Bermudez, E; Pryor, W A ^[1]

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1. Louisiana State Univ., Baton Rouge (United States)

The ozonation products of cholesterol, which are of interest as possible biomarkers of O3 exposure, were studied by derivatization with 2,4-dinitrophenylhydrazine (DNPH). The DNPH derivatization of 3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al (2) produces the expected trans (3b) and cis (3c) derivatives of 3 beta-hydroxy-5-oxo-5,6-secocholestan-6-al, and the unexpected DNPH derivative of 3,5-dihydroxy-B-norcholestane-6-carboxaldehyde (3a). The structures of 3a, 3b, and 3c were identified with 1H nuclear magnetic resonance (NMR), 13C NMR, DEPT, COSY, and H-C correlation two-dimensional NMR techniques, and by comparison with the spectra of known compounds. A possible mechanism involving an enamine functionality is proposed for the formation of 3a. The ratio of 3a/(3b + 3c) depends on the concentration of acid used and the reaction time.

• OSTI ID: 6146650
• Journal Information: Steroids; (United States), Journal Name: Steroids; (United States) Vol. 58:5; ISSN 0039-128X; ISSN STEDAM
• Country of Publication: United States
• Language: English

Related Subjects

550200* -- Biochemistry
560300 -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
BIOLOGICAL EFFECTS
CHEMICAL REACTIONS
CHOLESTEROL
DERIVATIZATION
HYDRAZINE
HYDROXY COMPOUNDS
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
NITROGEN COMPOUNDS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
OZONE
OZONIZATION
RESONANCE
STEROIDS
STEROLS