Electrochemical oxidation of cholesterol in acetonitrile leads to the formation of cholesta-4,6-dien-3-one

Electrochimica Acta

Volumn 54, Issue 26, 2009, Pages 6412-6416

  Hosokawa, Yu Ya ^a   Hakamata, Hideki ^a   Murakami, Tomonori ^a,b   Aoyagi, Sakae ^a   Kuroda, Minpei ^a   Mimaki, Yoshihiro ^a   Ito, Ayumi ^a   Morosawa, Sayaka ^a   Kusu, Fumiyo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b DAIICHI SANKYO CO   (Japan)

Author keywords

Cholesta 4,6 dien 3 one; Cholesterol; Electrochemical oxidation; Infrared spectroscopy; Matrix assisted laser desorption ionization time of flight mass spectrometry; Nuclear magnetic resonance

Indexed keywords

2-PROPANOL; CHOLESTA-4,6-DIEN-3-ONE; DETECTION MECHANISM; ELECTROCHEMICAL DETECTION; ELECTROCHEMICAL PROCESS; GAIN INSIGHT; GLASSY CARBON ELECTRODES; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX-ASSISTED LASER DESORPTION/IONIZATION TIME-OF-FLIGHT MASS SPECTROMETRY; OXIDATION REACTIONS; SPECTRAL DATA; TWO-DIMENSIONAL NUCLEAR MAGNETIC RESONANCE;

ACETONITRILE; CHOLESTEROL; CHROMATOGRAPHIC ANALYSIS; DESORPTION; ELECTROCHEMICAL CELLS; GLASS MEMBRANE ELECTRODES; HIGH PRESSURE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; LASERS; MASS SPECTROMETERS; MASS SPECTROMETRY; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SPECTROSCOPIC ANALYSIS;

ELECTROCHEMICAL OXIDATION;

EID: 69249115761     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2009.06.005     Document Type: Article

References (22)

1. Smith L.L. Cholesterol Autoxidation (1981), Plenum Press, New York, USA
2. Schroepfer G.J. Physiol. Rev. 80 (2000) 361
3. Bjorkhem I., and Diczfalusy U. Arterioscler. Thromb. Vasc. Biol. 22 (2002) 734
4. Ory D.S. Circ. Res. 95 (2004) 660
5. Djerassi C. Steroid Reactions: An Outline for Organic Chemists (1963), Holden-Day, Inc., San Francisco, USA
6. Uemi M., Ronsein G.E., Miyamoto S., Medeiros M.H.G., and Di Mascio P. Chem. Res. Toxicol. 22 (2009) 875
7. Brinkhorst J., Nara S.J., and Pratt D.A. J. Am. Chem. Soc. 130 (2008) 12224
8. Görög S. Quantitative Analysis of Steroids (1983), Elsevier Scientific Publishing Company, Inc., Amsterdam, The Netherlands
9. Groves J.T., and Neumann R. J. Org. Chem. 53 (1988) 3891
10. Maki S., Konno K., and Takayama H. Tetrahedron Lett. 38 (1997) 7067
11. Wu X., Song C., Cheng F., and Zhang W. J. Electroanal. Chem. 327 (1992) 321
12. Kowalski J., Ploszynska J., Sobkowiak A., Morzycki J.W., and Wilczewska A.Z. J. Electroanal. Chem. 585 (2005) 275
13. Kowalski J., Lotowski Z., Morzycki J.W., Ploszynska J., Sobkowiak A., and Wilczewska A.Z. Steroids 73 (2008) 543
14. Hojo K., Hakamata H., Ito A., Kotani A., Furukawa C., Hosokawa Y.Y., and Kusu F. J. Chromatogr. A 1166 (2007) 135
15. Arai K., Sato T., Tamanouchi H., Ohtomo M., Takamura K., Sueoka T., and Kusu F. Electrochim. Acta 45 (2000) 3029
16. Yang B., Arai K., and Kusu F. Electrochemistry 69 (2001) 519
17. Schiller J., Arnhold J., Glander H.J., and Arnold K. Chem. Phys. Lipids 106 (2000) 145
18. Schiller J., Zschörnig O., Petković M., Müller M., Arnhold J., and Arnold K. J. Lipid Res. 42 (2001) 1501
19. Gottlieb H.E., Kotlyar V., and Nudelman A. J. Org. Chem. 62 (1997) 7512
20. Kim E., and Ma E. Steroids 72 (2007) 360
21. Minami I., Takahashi K., Shimizu I., Kimura T., and Tsuji J. Tetrahedron 42 (1986) 2971
22. Doering W.E., Birladeanu L., Cheng X.H., Kitagawa T., and Sarma K. J. Am. Chem. Soc. 113 (1991) 4558