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700021P

Avanti

27-hydroxycholesterol

Avanti Research™ - A Croda Brand

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :
C27H46O2
Numéro CAS:
20380-11-4
Poids moléculaire :
402.65
Numéro MDL:
MFCD00272990
Code UNSPSC :
12352211
Nomenclature NACRES :
NA.25

Description

cholest-(25R)-5-ene-3β,27-diol

Essai

>99% (TLC)

Forme

powder

Conditionnement

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

Fabricant/nom de marque

Avanti Research™ - A Croda Brand

Conditions d'expédition

dry ice

Température de stockage

−20°C

Chaîne SMILES 

O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)[C@@H](CCC[C@H](CO)C)C)(CC3)C)CC=C2C1)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

Clé InChI

FYHRJWMENCALJY-YSQMORBQSA-N

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Catégories apparentées

Description générale

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

Actions biochimiques/physiologiques

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.

Conditionnement

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)

Informations légales

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Souvent commandé avec ce produit

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

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.
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
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.
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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