Cholesterol-5alpha,6alpha-epoxide

5α,6α-Epoxycholesterol (1250-95-9) is a naturally occurring metabolite of cholesterol. It is a major oxysterol found in processed food1and has been implicated in atherosclerosis2,3. 5α,6α-Epoxycholesterol has been found to be an endogenous ligand for LXR (EC50= 76 nM).4

Cholesterol 5alpha,6alpha-epoxide is used in the generation of oxysterols and in the studies of the biological significance of oxysterols.

Cholesterol 5α, 6α-epoxide was incorporated in culture medium of human arterial endothelial cells to study oxysterol-induced toxicity.

5α,6α-epoxycholestanol has been used as a sterol internal standard in ultra-performance liquid chromatography–high resolution mass spectrometry (UPLC-ESI-HRMS) analysis to quantify mice brain sterols. It may be used in calibration curve generation for the quantification of phytosterols in food samples and as an internal standard for oxysterol quantification in biological samples by gas chromatography-mass spectrometry (GC-MS)

ChEBI: 5,6alpha-epoxy-5alpha-cholestan-3beta-ol is a 3beta-hydroxy steroid, an oxysterol and an epoxy steroid. It derives from a hydride of a 5alpha-cholestane.

5α,6α-epoxycholestanol (5α,6α-EC) is generated by cholesterol epoxidation and is a diastereoisomer of 5β,6β-epoxycholestanol (5β,6β-EC).

Cholesterol 5α, 6α-epoxide is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis. The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation. Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.

[1] GABRIELLA LEONARDUZZI  Giuseppe P  Barbara Sottero. Oxidized products of cholesterol: dietary and metabolic origin, and proatherosclerotic effects (review)[J]. Journal of Nutritional Biochemistry, 2002, 13 12: Pages 700-710. DOI:10.1016/s0955-2863(02)00222-x
[2] I BJÖRKHEM. Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia.[J]. Journal of Lipid Research, 1988, 29 8: 1031-1038.
[3] ILONA STAPRANS. The role of dietary oxidized cholesterol and oxidized fatty acids in the development of atherosclerosis[J]. Molecular Nutrition & Food Research, 2005, 49 11: 1075-1082. DOI:10.1002/mnfr.200500063
[4] THOMAS J BERRODIN. Identification of 5α, 6α-epoxycholesterol as a novel modulator of liver X receptor activity.[J]. ACS Applied Electronic Materials, 2010: 1046-1058. DOI:10.1124/mol.110.065193