Electrochemical oxidation of cholesterol in acetonitrile leads to the formation of cholesta-4,6-dien-3-one |
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Authors: | Yu-Ya Hosokawa Hideki Hakamata Tomonori Murakami Sakae Aoyagi Minpei Kuroda Yoshihiro Mimaki Ayumi Ito Sayaka Morosawa Fumiyo Kusu |
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Affiliation: | a Department of Analytical Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan b Analytical and Quality Evaluation Research Laboratories, Daiichi-Sankyo Co. Ltd., 1-12-1 Shinomiya, Hiratsuka, Kanagawa 254-0014, Japan c Department of Medicinal Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan d Laboratory of Medicinal Pharmacognosy, School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan |
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Abstract: | Cholesterol was shown to be oxidized at the glassy carbon electrode in an acetonitrile–2-propanol mixture and this oxidation reaction was applied to the determination of serum total cholesterol by high-performance liquid chromatography with electrochemical detection (K. Hojo, H. Hakamata, A. Ito, A. Kotani, C. Furukawa, Y.Y. Hosokawa, F. Kusu, J. Chromatogr. A 1166 (2007) 135–141). To gain insight into the detection mechanisms of cholesterol, an electrolytic product of cholesterol was collected and characterized by infrared spectroscopy, one- and two-dimensional nuclear magnetic resonance, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. The three techniques, together with comparisons of literature spectral data, confirmed the formation of cholesta-4,6-dien-3-one. The conversion of cholesterol to cholesta-4,6-dien-3-one, a four-electron, four-proton electrochemical process, has been proposed as an electrochemical oxidation mechanism of cholesterol in acetonitrile. |
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Keywords: | Electrochemical oxidation Cholesterol Cholesta-4 6-dien-3-one Infrared spectroscopy Nuclear magnetic resonance Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry |
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