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700021P

Avanti

27-hydroxycholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H46O2
CAS Number:
20380-11-4
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

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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

also commonly purchased with this product

Product No.
Description
Pricing

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’.

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Valéria S Nunes et al.
Clinica chimica acta; international journal of clinical chemistry, 433, 169-173 (2014-03-25)
HDL is considered the most important mechanism for the excretion of intracellular cholesterol. The liver is the only organ capable to metabolize cholesterol into bile acid. The enzymatic conversion of cholesterol to bile acid is dependent on the cytochrome P450
Marjan Shafaati et al.
Journal of lipid research, 52(5), 1004-1010 (2011-02-22)
There is a significant flux of the neurotoxic oxysterol 27-hydroxycholesterol (27OHC) from the circulation across the blood-brain barrier. Because there is a correlation between 27OHC and cholesterol in the circulation and lipoprotein-bound cholesterol does not pass the blood-brain barrier, we
Sun-Mi Kim et al.
Biochemical and biophysical research communications, 430(2), 454-459 (2012-12-19)
Enhanced production of TNF-α from macrophages promotes development and instability of atherosclerotic plaques, but involvement of lipid component in TNF-α production has not been clarified in atherosclerosis. We attempted to determine whether cholesterol oxidation products (oxysterols) could modify TNF-α production.
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
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
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