C2773

Cholesterol 5α,6α-epoxide

• Synonym(s): 5α,6α-Epoxycholestan-3β-ol
• Empirical Formula (Hill Notation): C₂₇H₄₆O₂
• CAS Number: 1250-95-9
• Molecular Weight: 402.65
• NACRES: NA.77
• PubChem Substance ID: 24892526
• UNSPSC Code: 41141804
• EC Number: 215-007-6
• MDL number: MFCD00046980

Properties

• assay: ≥80%
• 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

Description

Application

Cholesterol 5α, 6α-epoxide was incorporated in culture medium of human arterial endothelial cells to study oxysterol-induced toxicity.[1]

Biochem/physiol Actions

Cholesterol 5α, 6α-epoxide is an oxysterol, a cholesterol derivative by auto-oxidation. Oxysterols are non-genomic regulators of cholesterol homeostasis.[2] The biological effects include protein prenylation, apoptosis, modulation of sphingolipid metabolism and platelet aggregation.[3] Oxysterols bind to liver X receptors, modulate cholesterol efflux and decrease the uptake of cholesterol by the cells.[2]

Preparation Note

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)