700035P
Avanti
7β-hydroxycholesterol
Avanti Research™ - A Croda Brand
Synonym(s):
cholest-5-ene-3b,7b-diol; 110809
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.25
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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
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
also commonly purchased with this product
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Amira Zarrouk et al.
Biochimie, 153, 210-219 (2018-07-14)
Some oxysterols resulting either from enzymatic oxidation or autoxidation of cholesterol are associated with age-related diseases including neurodegenerative diseases. Among these oxysterols, 7β-hydroxycholesterol (7β-OHC) is often found at increased levels in patients. It is therefore important to identify molecules or
M P Ares et al.
Atherosclerosis, 153(1), 23-35 (2000-11-04)
In the present study, we characterize the early cytotoxic effects of 7beta-hydroxycholesterol, a major cytotoxin in oxidized LDL, in human aortic smooth muscle cells. Within a few minutes after addition, 7beta-hydroxycholesterol induced Ca(2+) oscillations with a frequency of approximately 0.3-0.4
Kyoung Ah Kang et al.
Biological & pharmaceutical bulletin, 28(8), 1377-1380 (2005-08-05)
The cytotoxic activity of 7beta-hydroxycholesterol (7beta-OHC) was evaluated on human NCI-H460 lung cancer cells. 7beta-OHC decreased clonogenic survival of NCI-H460 in a dose dependent pattern. 7beta-OHC induced apoptosis in NCI-H460, with the characteristic features like increase in sub-G(1) hypodiploid (apoptotic)
Changguang Wang et al.
International journal of pharmaceutics, 569, 118576-118576 (2019-07-31)
Cholesterol is one of the major structural constituents in a liposomal bilayer. Cholesterol is susceptible to various reactions in the presence of oxygen, heat, light, certain metals, and radicals during manufacturing or storage, which may cause to generate cholesterol oxidation
Sinead Lordan et al.
International journal of toxicology, 27(3), 279-285 (2008-06-24)
The induction of apoptosis in cells of the arterial wall is a critical event in the development of atheroma. 7beta-Hydroxycholesterol (7beta-OH) and cholesterol-5beta,6beta-epoxide (beta-epoxide) are components of oxLDL and have previously been shown to be potent inducers of apoptosis. However
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