SMILES string
O1[C@@]32[C@@H]1C[C@@H]4[C@@H]([C@]3(CC[C@@H](C2)O)C)CC[C@]5([C@H]4CC[C@@H]5[C@@H](CCCC(C)C)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
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
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
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
5alpha, 6alpha-Epoxyphytosterols and 5alpha, 6alpha-Epoxycholesterol Increase Oxidative Stress in Rats on Low-Cholesterol Diet
Wielkoszynski T, et al
Oxidative Medicine and Cellular Longevity, 2019 (2019)
Cholesterol is superior to 7-ketocholesterol or 7alpha-hydroxycholesterol as an allosteric activator for acyl-coenzyme A: cholesterol acyltransferase 1
Zhang Y, et al.
The Journal of Biological Chemistry, 278(13), 11642-11647 (2003)
Identification of 5alpha, 6alpha-epoxycholesterol as a novel modulator of liver X receptor activity
Berrodin TJ, et al.
Molecular Pharmacology, 78(6), 1046-1058 (2010)
Development and validation of methodologies for the quantification of phytosterols and phytosterol oxidation products in cooked and baked food products
Menendez-Carreno M, et al.
Journal of Chromatography A, 1428, 316-325 (2016)
Development of a novel method for quantification of sterols and oxysterols by UPLC-ESI-HRMS: application to a neuroinflammation rat model
Ayciriex S, et al.
Analytical and Bioanalytical Chemistry, 404(10), 3049-3059 (2012)
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