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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%

Niveau de qualité

100

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)

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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
Z H Feng et al.
Sheng li ke xue jin zhan [Progress in physiology], 30(1), 23-28 (2003-01-21)
Oxysterols, being oxygenated derivatives of cholesterol, are as many kinds as one hundred. They are found in the foodstuffs, the blood and arterial tissues of animals with hypercholesterolemia, the human atheroma, the foam cell from atherosclerotic tissues, as well as
A J O'Sullivan et al.
Journal of applied toxicology : JAT, 23(3), 191-197 (2003-06-10)
Cholesterol can be oxidized to form a variety of cholesterol oxidation products also known as oxysterols. The aims of the present study were to compare the cytotoxic effects of four oxysterols, namely 25-hydroxycholesterol (25-OHC), 7beta-hydroxycholesterol (7beta-OHC), cholesterol-5beta,6beta-epoxide (beta-epox) and cholesterol-5alpha,6alpha-epoxide
S Ferderbar et al.
Diabetes/metabolism research and reviews, 23(1), 35-42 (2006-04-25)
Oxidative stress plays an important role in the pathophysiology of diabetes mellitus. The aim of this study was to evaluate the formation of cholesterol oxides (ChOx) as biomarkers of oxidative stress in subjects with impaired glucose tolerance (IGT) and diabetes.
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
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