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Merck

700032P

Avanti

5α,6α-epoxycholestanol

Avanti Research - A Croda Brand

别名:

5α,6α-epoxy-cholesterol; 5α,6α-epoxy-5α-cholestan-3β-ol; cholesterol-5α,6α-epoxide; 110804

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About This Item

经验公式(希尔记法):
C27H46O2
CAS号:
分子量:
402.65
分類程式碼代碼:
12352211
NACRES:
NA.25

描述

cholestanol, 5α,6α-epoxy

化驗

>99% (TLC)

形狀

powder

包裝

pkg of 1 × 5 mg (700032P-5mg)

製造商/商標名

Avanti Research - A Croda Brand

運輸包裝

dry ice

儲存溫度

−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 密鑰

PRYIJAGAEJZDBO-ZEQHCUNVSA-N

一般說明

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

應用

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)

生化/生理作用

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.

包裝

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

法律資訊

Avanti Research is a trademark of Avanti Polar Lipids, LLC

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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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)
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)
The influence of an obesogenic diet on oxysterol metabolism in C57BL/6J mice
Wooten JS, et al.
Cholesterol, 2014 (2014)
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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