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C2648

Sigma-Aldrich

Cholesterol 5β,6β-epoxide

≥98%

Sinônimo(s):

5β,6β-Epoxycholestan-3β-ol

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About This Item

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

Ensaio

≥98%

forma

powder

grupo funcional

epoxy

Condições de expedição

ambient

temperatura de armazenamento

room temp

cadeia de caracteres 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

chave InChI

PRYIJAGAEJZDBO-UHFFFAOYSA-N

Aplicação

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

Ações bioquímicas/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 classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Sigma-Aldrich

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Sigma-Aldrich

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3-Chlorobenzoic acid ReagentPlus®, ≥99%

Sigma-Aldrich

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Cholesteryl pelargonate 97%

Sigma-Aldrich

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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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