Todas las fotos(2)

700035P

Avanti

7β-hydroxycholesterol

cholest-5-en-3β,7β-diol, powder

Sinónimos:
cholest-5-ene-3b,7b-diol; 110809
Empirical Formula (Hill Notation):
C27H46O2
Número de CAS:
Peso molecular:
402.65
NACRES:
NA.25

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)

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-25mg)
5 mL Amber Glass Screw Cap Vial (700035P-10mg)
5 mL Amber Glass Screw Cap Vial (700035P-5mg)

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificado de Análisis

Certificado de origen

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...
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)...
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...
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...
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...

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