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700140P

Avanti

6-keto-5α-hydroxycholesterol

Avanti Research™ - A Croda Brand 700140P, powder

Synonym(s):

3β,5α-dihydroxy-cholestan-6-one

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About This Item

Empirical Formula (Hill Notation):
C27H46O3
CAS Number:
13027-33-3
Molecular Weight:
418.65
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 5 mg (700140P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 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)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

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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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
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)
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
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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