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Merck

C2648

Cholesterol 5β,6β-epoxide

≥98%

Synonym(s):

5β,6β-Epoxycholestan-3β-ol

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£85.00

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
4025-59-6
Molecular Weight:
402.65
MDL number:
MFCD00201258
UNSPSC Code:
12352211
PubChem Substance ID:
24892511
NACRES:
NA.28

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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

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1 of 4

This Item
H6891D6128C8503
Cholesterol 5β,6β-epoxide ≥98%

Sigma-Aldrich

C2648

Cholesterol 5β,6β-epoxide

7β-Hydroxycholesterol ≥95%

Sigma-Aldrich

H6891

7β-Hydroxycholesterol

5α-Cholestan-3β-ol ≥95%

Sigma-Aldrich

D6128

5α-Cholestan-3β-ol

Cholesterol from sheep wool, ≥92.5% (GC), powder

Sigma-Aldrich

C8503

Cholesterol

functional group

epoxy

functional group

hydroxyl

functional group

-

functional group

-

assay

≥98%

assay

≥95%

assay

≥95%

assay

≥92.5% (GC)

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

form

powder

form

powder

form

powder

form

powder

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

Application

Cholesterol 5β,6β-epoxide was used to treat PC12 cells or HepG2 and Caco-2 cells[1] to study the effects of cholesterol oxidation.[2]

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 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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Certificates of Analysis (COA)

Lot/Batch Number
0000488086
0000488086
0000386090
0000366286
0000366286

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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
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
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.
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