Skip to Content
Merck
All Photos(2)

Key Documents

700021P

Avanti

27-hydroxycholesterol

Avanti Research - A Croda Brand

Synonym(s):

27-hydroxycholesterol(25R); cholest-5-ene-3β,27-diol, (25R); 110818

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
Molecular Weight:
402.65
UNSPSC Code:
12352211
NACRES:
NA.25

description

cholest-(25R)-5-ene-3β,27-diol

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700021P-1mg)
pkg of 1 × 25 mg (700021P-25mg)
pkg of 1 × 5 mg (700021P-5mg)

manufacturer/tradename

Avanti Research - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

InChI key

FYHRJWMENCALJY-YSQMORBQSA-N

Looking for similar products? Visit Product Comparison Guide

General description

27-hydroxycholesterol (27-HC) is synthesized from cholesterol by the action of sterol 27-hydroxylase in liver. It is an abundant oxysterol in the circulation ranging from 0.15 to 0.73 μM. 27-HC serves as a substrate for bile synthesis.

Application

27-hydroxycholesterol has been used:
  • to test its inhibitory effect on hepatic lipid accumulation
  • as liver X receptor (LXR) ligand in breast cancer cell lines
  • as a control in liquid chromatography with tandem mass spectrometry (LC-MS-MS) for the quantitation of 25-OHC in jejunum samples

Biochem/physiol Actions

27-hydroxycholesterol (27-HC) is a weak liver X receptor (LXR) agonist and a selective estrogen receptor modulator (SERM). Elevated levels of 27-HC is observed in hypercholesterolemia. 27-HC is implicated in breast cancer tumor and glioblastoma progression. 27-HC may help in treating non-alcoholic steatohepatitis. Elevated levels of 27-HC is associated with atherosclerotic lesions.

Packaging

5 mL Amber Glass Screw Cap Vial (700021P-1mg)
5 mL Amber Glass Screw Cap Vial (700021P-25mg)
5 mL Amber Glass Screw Cap Vial (700021P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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’.

Already Own This Product?

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

Visit the Document Library

Jacques E Rossouw et al.
Circulation, 126(13), 1577-1586 (2012-08-31)
Menopausal hormone therapy (MHT) increases the risk of coronary heart disease (CHD) in older women with elevated low-density lipoprotein (LDLC) levels. The endogenous estrogen receptor antagonist 27-hydroxycholesterol (27OHC) is correlated with LDLC levels and may block the beneficial effects of
Sun-Mi Kim et al.
Toxicology and applied pharmacology, 274(3), 462-470 (2013-12-29)
Th1 lymphocytes are predominant in atherosclerotic lesions. However, mechanisms involved in the Th1 predominance are unknown. We have investigated the possibility of Th1 lymphocyte recruitment in a cholesterol-rich milieu. A high cholesterol diet resulted in enhanced expression of CCR5 ligands
Ratna Karuna et al.
Atherosclerosis, 214(2), 448-455 (2010-12-07)
Secretion of 27-hydroxycholesterol (27OHC) from macrophages is considered as an alternative to HDL-mediated reverse transport of excess cholesterol. We investigated 27OHC-concentrations in plasma of humans and mice with monogenic disorders of HDL metabolism. As compared to family controls mutations in
Maura Heverin et al.
Journal of lipid research, 46(5), 1047-1052 (2005-03-03)
Side chain oxidized oxysterols have a unique ability to traverse lipophilic membranes. We tested the hypothesis that there is a net flux of 27-hydroxycholesterol from the circulation into the brain using plasma samples collected from the internal jugular vein and
Qian Wu et al.
Cell reports, 5(3), 637-645 (2013-11-12)
To date, estrogen is the only known endogenous estrogen receptor (ER) ligand that promotes ER+ breast tumor growth. We report that the cholesterol metabolite 27-hydroxycholesterol (27HC) stimulates MCF-7 cell xenograft growth in mice. More importantly, in ER+ breast cancer patients

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