CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Property

Melting point:

147 °C

Boiling point:

464.74°C (rough estimate)

Density 

0.9932 (rough estimate)

refractive index 

1.4480 (estimate)

storage temp. 

-20°C

solubility 

Soluble in DMSO (up to 10 mg/ml) orin Ethanol (up to 10 mg/ml).

form 

solid

pka

15.20±0.70(Predicted)

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.

Safety

WGK Germany 

3

RTECS 

FZ6360000

Hazard and Precautionary Statements (GHS)

CHOLESTEROL-5ALPHA,6ALPHA-EPOXIDE Chemical Properties,Usage,Production

Description

5α,6α-Epoxycholesterol (1250-95-9) is a naturally occurring metabolite of cholesterol.? It is a major oxysterol found in processed food1?and has been implicated in atherosclerosis2,3. 5α,6α-Epoxycholesterol has been found to be an endogenous ligand for LXR (EC50?= 76 nM).4

Uses

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

Uses

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

Uses

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)

Definition

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.

General Description

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

Biochem/physiol Actions

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.

References

1) Leonarduzzi?et al.?(2002),?Oxidized products of cholesterol: dietary and metabolic origin, and proatherosclerotic effect (review);?J.?Nutr. Biochem.,?13?700 2) Bj?rkhem?et al. (1988),?Assay of unesterified cholesterol-5,6-epoxide in human serum by isotope dilution mass spectrometry. Levels in the healthy state and in hyperlipoproteinemia; J. Lipid Res.,?29?1031 3) Staprans?et al.?(2005),?The role of dietary oxidized cholesterol and oxidized fatty acids in the development of atherosclerosis; Mol. Nutr. Food Res.,?49?1075 4) Berrodin?et al. (2010),?Identification of 5α,6α-Epoxycholesterol as a novel modulator of Liver X Receptor; Mol. Pharmacol.,?78?1046