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Merck

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:
Peso molecular:
402.65
Número MDL:
Código UNSPSC:
12352211
ID de la sustancia en PubChem:
NACRES:
NA.28

Nivel de calidad

Ensayo

≥98%

Formulario

powder

grupo funcional

epoxy

Condiciones de envío

ambient

temp. de almacenamiento

room temp

cadena 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

Clave InChI

PRYIJAGAEJZDBO-UHFFFAOYSA-N

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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


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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
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
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)
Marc Poirot et al.
Biochimie, 95(3), 622-631 (2012-05-23)
In the nineteen sixties it was proposed that cholesterol might be involved in the etiology of cancers and cholesterol oxidation products were suspected of being causative agents. Researchers had focused their attention on cholesterol-5,6-epoxides (5,6-ECs) based on several lines of

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