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C2648

Sigma-Aldrich

Cholesterol 5β,6β-epoxide

≥98%

Synonym(s):

5β,6β-Epoxycholestan-3β-ol

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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

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘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
Y W Cheng et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 43(4), 617-622 (2005-02-22)
The mutagenicity of oxysterols, cholesterol-3beta,5alpha,6beta-triol (alpha-Triol), 7-keto-cholesterol (7-Keto) and cholesterol-5alpha,6alpha-epoxide (alpha-Epox) were examined by the Ames method and chromosome aberration test in this study. Only alpha-Triol concentration-dependently caused an increase of bacterial revertants in the absence of metabolic activating enzymes
Lisa Ryan et al.
The British journal of nutrition, 94(4), 519-525 (2005-10-04)
Oxysterols are oxygenated derivatives of cholesterol that may be formed endogenously or absorbed from the diet. Significant amounts of oxysterols have frequently been identified in foods of animal origin, in particular highly processed foods. To date, oxysterols have been shown
Patrik Johansson et al.
Journal of molecular biology, 351(5), 1048-1056 (2005-07-30)
Epoxide hydrolases are vital to many organisms by virtue of their roles in detoxification, metabolism and processing of signaling molecules. The Mycobacterium tuberculosis genome encodes an unusually large number of epoxide hydrolases, suggesting that they might be of particular importance
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