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Key Documents

C2773

Sigma-Aldrich

Cholesterol 5α,6α-epoxide

Synonym(s):

5α,6α-Epoxycholestan-3β-ol

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
EC Number:
MDL number:
UNSPSC Code:
41141804
PubChem Substance ID:
NACRES:
NA.77

Assay

≥80%

Quality Level

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/t18-,19+,20+,21-,22+,23+,24+,25-,26-,27+/m1/s1

InChI key

PRYIJAGAEJZDBO-ZEQHCUNVSA-N

Related Categories

Application

Cholesterol 5α, 6α-epoxide was incorporated in culture medium of human arterial endothelial cells to study oxysterol-induced toxicity.

Biochem/physiol Actions

Cholesterol 5α, 6α-epoxide is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis. The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation. Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.

Preparation Note

Cholesterol 5α, 6α-epoxide yields clear, colorless solution in chloroform at 50 mg/ml.

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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