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C2773

Sigma-Aldrich

Cholesterol 5α,6α-epoxide

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Synonym(s):
5α,6α-Epoxycholestan-3β-ol
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥80%

Quality Level

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

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This Item
D6128C9377C1129
Cholesterol 5α,6α-epoxide

C2773

Cholesterol 5α,6α-epoxide

5α-Cholestan-3β-ol ≥95%

D6128

5α-Cholestan-3β-ol

Chenodeoxycholic acid

C9377

Chenodeoxycholic acid

Cholic acid from bovine and/or ovine, ≥98%

C1129

Cholic acid

functional group

epoxy

functional group

-

functional group

carboxylic acid

functional group

carboxylic acid

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

form

powder

form

powder

form

powder

form

powder

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
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.
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
L Ryan et al.
Cell biology and toxicology, 20(5), 313-323 (2005-02-03)
Oxysterols have been shown to induce apoptosis in a variety of cell lines. The mechanism of oxysterol-induced apoptosis is mainly known at the post-mitochondrial level. The aim of the present study was to compare the pathway of apoptosis induced by

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