700140P
Avanti
6-keto-5α-hydroxycholesterol
Avanti Polar Lipids 700140P, powder
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Synonym(s):
3β,5α-dihydroxy-cholestan-6-one
Empirical Formula (Hill Notation):
C27H46O3
Recommended Products
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 5 mg (700140P-5mg)
manufacturer/tradename
Avanti Polar Lipids 700140P
shipped in
dry ice
storage temp.
−20°C
InChI
1S/C27H46O3/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24(29)27(30)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-23,28,30H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,25-,26-,27+/m1/s1
InChI key
SJZZRXMQSAXCFD-ZCBMJONGSA-N
General description
6-keto-5α-hydroxycholesterol, also known as 6-oxo-cholestan-3β,5α-diol (OCDO), is synthesized from the oxidation of 5β, 6β-epoxycholesterol in the presence of enzyme cholesterol epoxide hydrolase. It is also synthesized from cholestane-3β,5α,6β-triol by the enzyme 11β-hydroxysteroid dehydrogenase type II . The enzyme 11β-hydroxysteroid dehydrogenase type I catalyzes the reduction of OCDO to cholestane-3β,5α,6β-triol.
Biochem/physiol Actions
6-keto-5α-hydroxycholesterol favors tumor progression. cholestan-6-oxo-3β,5α-diolelicits cytotoxicity towards human bronchial 16-HBE cells and plays a key role in mediating cell necrosis post ozone exposure. It is an oncometabolite, which promotes breast cancer progression and also blocks chemotaxis mediated by polymorphonuclear leukocytes.
Packaging
5 mL Amber Glass Screw Cap Vial (700140P-5mg)
Certificates of Analysis (COA)
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Marc Poirot et al.
Biochimie, 153, 139-149 (2018-04-15)
Oxygenation products of cholesterol, named oxysterols, were suspected since the 20th century to be involved in carcinogenesis. Among the family of oxysterol molecules, cholesterol-5,6-epoxides (5,6-EC) retained the attention of scientists because they contain a putative alkylating epoxide group. However, studies
Maud Voisin et al.
Biochemical and biophysical research communications, 446(3), 782-785 (2014-02-11)
Cholesterol metabolism has been recently linked to cancer, highlighting the importance of the characterization of new metabolic pathways in the sterol series. One of these pathways is centered on cholesterol-5,6-epoxides (5,6-ECs). 5,6-ECs can either generate dendrogenin A, a tumor suppressor
Melissa K Pulfer et al.
The Journal of pharmacology and experimental therapeutics, 312(1), 256-264 (2004-08-19)
Ozone toxicity in the lung is thought to be mediated by products derived from the reaction of ozone with components of the lung epithelial lining fluid. Cholesterol is an abundant component of this epithelial lining fluid, and it is susceptible
Cholesterol, reactive oxygen species, and the formation of biologically active mediators.
Robert C Murphy et al.
The Journal of biological chemistry, 283(23), 15521-15525 (2008-02-21)
Melissa K Pulfer et al.
The Journal of biological chemistry, 279(25), 26331-26338 (2004-04-21)
Exposure of the lung to concentrations of ozone found in ambient air is known to cause toxicity to the epithelial cells of the lung. Because of the chemical reactivity of ozone, it likely reacts with target molecules in pulmonary surfactant
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