SMILES string
C[C@]12CC[C@H]([C@](CC[C@H](O)C3)(C)[C@]3(O4)[C@H]4C5)[C@@H]5[C@@H]1CC[C@@H]2[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-DTLXENBRSA-N
description
cholestanol, 5β,6β-epoxy
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 5 mg (700033P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
shipped in
dry ice
storage temp.
−20°C
General description
5β,6β-epoxycholestanol (5β,6β-EC) is generated by cholesterol epoxidation and is a diastereoisomer of 5α,6α-epoxycholestanol (5α,6α-EC).
Application
5β,6β-epoxycholestanol may be used as a oxy-mix component in treating human colorectal adenocarcinoma CaCo-2 cells to test its effect on toll-like receptor (TLR) expression, in the preparation of langmuir monolayers for isotherm studies, as an internal standard for gas chromatography-mass spectrometry (GC–MS) chromatograms
Biochem/physiol Actions
5β,6β-epoxycholestanol (5β,6β-EC) is associated with human carotid plaques and is not down-regulated by apolipoprotein A1 (apoA-I) protein. 5,6β-EC along with 5α,6α-epoxycholesterol and other oxysterols are reported to be associated with Alzheimer′s disease. It is catabolized by the enzyme cholesterol-5,6-epoxide hydrolase (ChEH) enzyme to 3β,5α,6β-triol. 5β,6β-EC elicits cytotoxic and inflammatory properties.
Packaging
5 mL PTFE Vial with Screw Cap (700033P-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
Cholesterol Acceptors Regulate the Lipidome of Macrophage Foam Cells
Paul A, et al.
International Journal of Molecular Sciences, 20(15), 3784-3784 (2019)
Fast LC-MS/MS analysis of free oxysterols derived from reactive oxygen species in human plasma and carotid plaque
Helmschrodt C, et al.
Clinica Chimica Acta; International Journal of Clinical Chemistry, 425, 3-8 (2013)
Gas chromatography-mass spectrometry determination of conjugated linoleic acids and cholesterol oxides and their stability in a model system
Yen TY, et al.
Analytical Biochemistry, 400(1), 130-138 (2010)
A dietary mixture of oxysterols induces in vitro intestinal inflammation through TLR2/4 activation: The protective effect of cocoa bean shells
Rossin D, et al.
Antioxidants, 8(6), 151-151 (2019)
Improvement of 5, 6alpha-epoxycholesterol, 5, 6beta-epoxycholesterol, cholestane-3beta, 5alpha, 6beta-triol and 6-oxo-cholestan-3beta, alpha-diol recovery for quantification by GC/MS
Soules R, et al.
Chemistry and Physics of Lipids, 207, 92-98 (2017)
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