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C2773

Sigma-Aldrich

Cholesterol 5α,6α-epoxide

Synonyme(s) :

5α,6α-Epoxycholestan-3β-ol

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About This Item

Formule empirique (notation de Hill):
C27H46O2
Numéro CAS:
1250-95-9
Poids moléculaire :
402.65
Numéro CE :
215-007-6
Numéro MDL:
MFCD00046980
Code UNSPSC :
41141804
ID de substance PubChem :
24892526
Nomenclature NACRES :
NA.77

Pureté

≥80%

Forme

powder

Groupe fonctionnel

epoxy

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne SMILES 

[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

Clé InChI

PRYIJAGAEJZDBO-ZEQHCUNVSA-N

Application

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

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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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
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
Y C O'Callaghan et al.
Cell biology and toxicology, 17(2), 127-137 (2001-08-14)
The cytotoxicity of the oxysterols 25-hydroxycholesterol, 7beta-hydroxycholesterol, cholesterol-5alpha,6alphaepoxide, cholesterol-5beta,6beta-epoxide, 19-hydroxycholesterol and 7-ketocholesterol was examined in U937 cells, a human monocytic blood cell line. 7beta-Hydroxycholesterol, cholesterol-5beta,6beta-epoxide, and 7-ketocholesterol, at 30 micromol/L concentration, were found to be cytotoxic to this cell line
Sinéad Lordan et al.
Journal of biochemical and molecular toxicology, 21(6), 362-372 (2007-11-13)
Oxidized low-density lipoprotein contains many potentially proatherogenic molecules, including oxysterols, which have been shown to induce apoptosis in various cell lines. The aim of this study was to investigate the pathway of apoptosis induced by oxidized low-density lipoprotein and the
May-Thu Ma et al.
Neuroscience letters, 476(1), 36-41 (2010-04-13)
Increase in levels of oxysterols or cholesterol oxidation products have been detected in brain areas undergoing neuroinflammation after excitotoxic injury, and the present study was carried out to elucidate possible effects of these products on exocytosis in rat pheochromocytoma-12 (PC12)
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