C2773
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:
Molecular Weight:
402.65
EC Number:
MDL number:
UNSPSC Code:
41141804
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
Related Categories
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
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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
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.
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
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
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
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