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C2773

Sigma-Aldrich

Cholesterol 5α,6α-epoxide

Synonym(s):

5α,6α-Epoxycholestan-3β-ol

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
1250-95-9
Molecular Weight:
402.65
EC Number:
215-007-6
MDL number:
MFCD00046980
UNSPSC Code:
41141804
PubChem Substance ID:
24892526
NACRES:
NA.77

Assay

≥80%

form

powder

functional group

epoxy

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@@]12[C@]([C@](CC[C@H](O)C3)(C)[C@@]3(O4)[C@@H]4C2)([H])CC[C@@]5(C)[C@@]1([H])CC[C@]5([H])[C@]([H])(C)CCCC(C)C

InChI

1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24+,25-,26-,27+/m1/s1

InChI key

PRYIJAGAEJZDBO-ZEQHCUNVSA-N

Application

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

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.

Preparation Note

Cholesterol 5α, 6α-epoxide yields clear, colorless solution in chloroform at 50 mg/ml.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anne Vejux et al.
Histochemistry and cell biology, 127(6), 609-624 (2007-01-18)
Oxysterols, mainly those oxidized at the C7 position, induce a complex mode of cell death exhibiting some characteristics of apoptosis associated with a rapid induction of lipid rich multilamellar cytoplasmic structures (myelin figures) observed in various pathologies including atherosclerosis. The
Chisato Ishimaru et al.
Lipids, 43(4), 373-382 (2008-01-25)
This paper describes the inhibitory activities of cholesterol derivatives such as cholesterol, sodium cholesteryl sulfate, cholesteryl-5alpha, 6alpha-epoxide, cholesteryl chloride, cholesteryl bromide, and cholesteryl hemisuccinate (compounds 1-6, respectively) against DNA polymerase (pol), DNA topoisomerase (topo), and human cancer cell growth. Among
Patrik Johansson et al.
Journal of molecular biology, 351(5), 1048-1056 (2005-07-30)
Epoxide hydrolases are vital to many organisms by virtue of their roles in detoxification, metabolism and processing of signaling molecules. The Mycobacterium tuberculosis genome encodes an unusually large number of epoxide hydrolases, suggesting that they might be of particular importance
Y W Cheng et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 43(4), 617-622 (2005-02-22)
The mutagenicity of oxysterols, cholesterol-3beta,5alpha,6beta-triol (alpha-Triol), 7-keto-cholesterol (7-Keto) and cholesterol-5alpha,6alpha-epoxide (alpha-Epox) were examined by the Ames method and chromosome aberration test in this study. Only alpha-Triol concentration-dependently caused an increase of bacterial revertants in the absence of metabolic activating enzymes
I Spyridopoulos et al.
Arteriosclerosis, thrombosis, and vascular biology, 21(3), 439-444 (2001-03-07)
Controversy exists about the net effect of alcohol on atherogenesis. A protective effect is assumed, especially from the tannins and phenolic compounds in red wine, owing to their inhibition of low density lipoprotein (LDL) oxidation. However, increased atherogenesis occurs in
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