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700047P

Avanti

5α,6α-epoxycholestanol-d7

Avanti Polar Lipids

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Synonym(s):
cholestanol, 5α,6α-epoxy-d7
Empirical Formula (Hill Notation):
C27H39O2D7
CAS Number:
Molecular Weight:
409.70
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700047P-1mg)

manufacturer/tradename

Avanti Polar Lipids

shipped in

dry ice

storage temp.

−20°C

General description

5α,6α-epoxycholestanol (5α,6α-EC) is generated by cholesterol epoxidation. 5α,6α-epoxycholestanol-d7 is a deuterated derivative of 5α,6α-EC. It is catabolized by the enzyme cholesterol-5,6-epoxide hydrolase (ChEH) enzyme to 3β,5α,6β-triol.

Application

5α,6α-epoxycholestanol-d7 has been used as an internal standard in isotope dilution-mass spectrometry analysis of heart mitochondrial samples. It may be used as an internal standard in liquid chromatography with tandem mass spectrometry (LC-MS-MS) analysis of plasma samples.

Biochem/physiol Actions

5α,6α-epoxycholestanol (5α,6α-EC) is a liver X receptor (LXR) antagonist. 5α,6α-EC is employed in anticancer treatments. It impairs redox state and affects atherogenesis. The levels of 5α,6α-EC are elevated in hypercholesterolemia. It mediates steroid receptor coactivator (SRC) recruitment.

Packaging

5 mL Amber Glass Screw Cap Vial (700047P-1mg)

also commonly purchased with this product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids


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Thomas J Berrodin et al.
Molecular pharmacology, 78(6), 1046-1058 (2010-09-15)
The liver X receptors (LXRα and LXRβ) are members of the nuclear receptor superfamily that function as key transcriptional regulators of a number of biological processes, including cholesterol homeostasis, lipid metabolism, and keratinocyte differentiation. Natural ligands that activate LXRs include
Regis Soules et al.
Chemistry and physics of lipids, 207(Pt B), 92-98 (2017-05-31)
5,6α-epoxycholesterol (5,6α-EC) and 5,6β-epoxycholesterol (5,6β-EC) are oxysterols involved in the anticancer pharmacology of the widely used antitumor drug tamoxifen. They are both metabolized into cholestane-3β,5α,6β-triol (CT) by the cholesterol-5,6-epoxide hydrolase (ChEH) enzyme, and CT is metabolized by an as-yet uncharacterized
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)
Myung-Jin Oh et al.
Journal of lipid research, 57(5), 791-808 (2016-03-19)
Endothelial biomechanics is emerging as a key factor in endothelial function. Here, we address the mechanisms of endothelial stiffening induced by oxidized LDL (oxLDL) and investigate the role of oxLDL in lumen formation. We show that oxLDL-induced endothelial stiffening is
Julien Musman et al.
Biochemical pharmacology, 142, 87-95 (2017-06-25)
A major cause of cell death during myocardial ischemia-reperfusion is mitochondrial dysfunction. We previously showed that the reperfusion of an ischemic myocardium was associated with an accumulation of cholesterol into mitochondria and a concomitant strong generation of auto-oxidized oxysterols. The

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