Skip to Content
Merck
All Photos(1)

Key Documents

Safety Information

700140P

Avanti

6-keto-5α-hydroxycholesterol

Avanti Research™ - A Croda Brand 700140P, powder

Synonym(s):

3β,5α-dihydroxy-cholestan-6-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

700140P-5MG:
700140P-VAR:
700140P-BULK:

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service