C2773
Cholesterol 5α,6α-epoxide
Sinônimo(s):
5α,6α-Epoxycholestan-3β-ol
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About This Item
Fórmula empírica (Notação de Hill):
C27H46O2
Número CAS:
Peso molecular:
402.65
Número CE:
Número MDL:
Código UNSPSC:
41141804
ID de substância PubChem:
NACRES:
NA.77
Preço e disponibilidade não estão disponíveis no momento.
Produtos recomendados
Ensaio
≥80%
Formulário
powder
grupo funcional
epoxy
Condições de expedição
ambient
temperatura de armazenamento
room temp
cadeia de caracteres 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
chave InChI
PRYIJAGAEJZDBO-ZEQHCUNVSA-N
Categorias relacionadas
Aplicação
Cholesterol 5α, 6α-epoxide was incorporated in culture medium of human arterial endothelial cells to study oxysterol-induced toxicity.[1]
Ações bioquímicas/fisiológicas
Cholesterol 5α, 6α-epoxide is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis.[2] The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation.[3] Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.[2]
Nota de preparo
Cholesterol 5α, 6α-epoxide yields clear, colorless solution in chloroform at 50 mg/ml.
Código de classe de armazenamento
11 - Combustible Solids
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
Equipamento de proteção individual
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
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
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)
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
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