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Key Documents

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C2648

Sigma-Aldrich

Cholesterol 5β,6β-epoxide

≥98%

Sinónimos:

5β,6β-Epoxycholestan-3β-ol

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About This Item

Fórmula empírica (notación de Hill):
C27H46O2
Número de CAS:
4025-59-6
Peso molecular:
402.65
MDL number:
MFCD00201258
UNSPSC Code:
12352211
PubChem Substance ID:
24892511
NACRES:
NA.28

Quality Level

100

assay

≥98%

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

InChI key

PRYIJAGAEJZDBO-UHFFFAOYSA-N

Application

Cholesterol 5β,6β-epoxide was used to treat PC12 cells or HepG2 and Caco-2 cells to study the effects of cholesterol oxidation.

Biochem/physiol Actions

Cholesterol 5β,6β-epoxide is an oxysterol produced as an oxidation product of cholesterol. Oxysterols are cytotoxic and induce death in monocytes, smooth muscle cells and endothelial cells. The mechanism of apoptosis induced by oxysterols may involve caspases or DNA fragmentation.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus.
Ferderbar S, Pereira EC, Apolinario E, et al.
Diabetes and Metabolism, 23, 35-42 (2007)
Zhi-Hua Chen et al.
FEBS letters, 580(2), 479-483 (2006-01-03)
The adaptive response induced by the lipid peroxidation products, such as phosphatidylcholine hydroperoxide, lysophosphatidylcholine (LysoPC), 15-deoxy-Delta(12,14)-prostaglandin J(2), 4-hydroxynonenal (4-HNE), hydroxyoctadecadienoic acid, 7-hydroxycholesterol, and cholesterol 5beta,6beta-epoxide, was investigated in this study. Although these products have been implicated in oxidative stress-related diseases
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
Christophe Morisseau
Biochimie, 95(1), 91-95 (2012-06-23)
Epoxide hydrolases (EH), enzymes present in all living organisms, transform epoxide-containing lipids to 1,2-diols by the addition of a molecule of water. Many of these oxygenated lipid substrates have potent biological activities: host defense, control of development, regulation of blood
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