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About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
description
cholest-5-en-3β,7β-diol
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 10 mg (700035P-10mg), pkg of 1 × 25 mg (700035P-25mg), pkg of 1 × 5 mg (700035P-5mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
shipped in
dry ice
storage temp.
−20°C
SMILES string
O[C@@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(C)C)C)(CC[C@@H]2[C@]4(CCC(CC4=C1)O)C)C
InChI
1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20?,21-,22+,23+,24+,25+,26+,27-/m1/s1
InChI key
OYXZMSRRJOYLLO-ISPKDCJXSA-N
General description
7β-hydroxycholesterol (7β-OHC) is an oxysterol synthesized by the oxidation of the low-density lipoprotein (LDL). It is primarily catabolized to bile acid in the liver.
Application
7β-hydroxycholesterol has been used:
- as an internal oxysterol standard in liquid chromatography–mass spectrometry (LC-MS) for the quantification of sterols associated with cholesterol biosynthesis in neurospheres post inhibitor AY9944 treatment
- to reconstitute high-density lipoprotein (HDL) for anti-apoptotic studies in insulinoma cell line INS1e
- as a cholesterol oxidation product standard in ultra high-performance liquid chromatography (UHPLC) coupled with high- resolution quadrupole time-of-flight (Q-TOF) mass spectrometry
Biochem/physiol Actions
7β-hydroxycholesterol (7β-OHC) favors apoptosis via caspase 8 based mitochondrial pathway. It also hinders cancer cell survival by generating reactive oxygen species(ROS). The levels of 7β-OHC are elevated in the cerebrospinal fluid of multiple sclerosis and Alzheimer′s disease (AD) patients. 7β-OHC also promotes oxiapoptophagy and demyelination. It activates mitogen-activated protein kinases and modulates intracellular Ca2+ homeostasis and may contribute to the disorganization of Golgi and endoplasmic reticulum membranes.
Packaging
5 mL Amber Glass Screw Cap Vial (700035P-10mg)
5 mL Amber Glass Screw Cap Vial (700035P-25mg)
5 mL Amber Glass Screw Cap Vial (700035P-5mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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