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C2648

Sigma-Aldrich

Cholesterol 5β,6β-epoxide

≥98%

Synonyme(s) :

5β,6β-Epoxycholestan-3β-ol

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About This Item

Formule empirique (notation de Hill):
C27H46O2
Numéro CAS:
4025-59-6
Poids moléculaire :
402.65
Numéro MDL:
MFCD00201258
Code UNSPSC :
12352211
ID de substance PubChem :
24892511
Nomenclature NACRES :
NA.28

Pureté

≥98%

Forme

powder

Groupe fonctionnel

epoxy

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne 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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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)
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
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.
D U Ahn et al.
Poultry science, 78(7), 1060-1064 (1999-07-15)
A study was conducted to develop a solvent system that will clean egg yolk samples and concentrate cholesterol oxides effectively before analysis. Cholesterol oxide standards or lipid samples (0.2 g) loaded onto a silicic column were washed with a portion
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