700032P

5α,6α-epoxycholestanol

Avanti Research^™ - A Croda Brand

• Synonym(s): 5α,6α-epoxy-cholesterol; 5α,6α-epoxy-5α-cholestan-3β-ol; cholesterol-5α,6α-epoxide; 110804
• Empirical Formula (Hill Notation): C₂₇H₄₆O₂
• CAS Number: 1250-95-9
• Molecular Weight: 402.65
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• description: cholestanol, 5α,6α-epoxy
• Assay: >99% (TLC)
• form: powder
• packaging: pkg of 1 × 5 mg (700032P-5mg)
• manufacturer/tradename: Avanti Research^™ - A Croda Brand
• shipped in: dry ice
• storage temp.: −20°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

General description

5α,6α-epoxycholestanol (5α,6α-EC) is generated by cholesterol epoxidation and is a diastereoisomer of 5β,6β-epoxycholestanol (5β,6β-EC).

Application

5α,6α-epoxycholestanol has been used as a sterol internal standard in ultra-performance liquid chromatography–high resolution mass spectrometry (UPLC-ESI-HRMS) analysis to quantify mice brain sterols. It may be used in calibration curve generation for the quantification of phytosterols in food samples and as an internal standard for oxysterol quantification in biological samples by gas chromatography-mass spectrometry (GC-MS)

Biochem/physiol Actions

5α,6α-epoxycholestanol (5α,6α-EC) is a liver X receptor (LXR) antagonist. It mimics cholesterol in phosphatidylcholine vesicles and is a substrate for acyl-coenzyme A:cholesterol acyltransferase (ACAT). 5α,6α-EC is employed in anticancer treatments. It is catabolized by the enzyme cholesterol-5,6-epoxide hydrolase (ChEH) enzyme to 3β,5α,6β-triol. 5α,6α-EC impairs redox state and affects atherogenesis. The levels of 5α,6α-EC is elevated in hypercholesterolemia and mediates steroid receptor coactivator (SRC) recruitment.

Packaging

5 mL Amber Glass Screw Cap Vial (700032P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable