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700021P

Avanti

27-hydroxycholesterol

Avanti Research™ - A Croda Brand

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C27H46O2
Número CAS:
20380-11-4
Peso molecular:
402.65
Número MDL:
MFCD00272990
Código UNSPSC:
12352211
NACRES:
NA.25

descrição

cholest-(25R)-5-ene-3β,27-diol

Ensaio

>99% (TLC)

Formulário

powder

embalagem

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

fabricante/nome comercial

Avanti Research™ - A Croda Brand

Condições de expedição

dry ice

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

FYHRJWMENCALJY-YSQMORBQSA-N

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Descrição geral

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.

Aplicação

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

Ações bioquímicas/fisiológicas

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.

Embalagem

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)

Informações legais

Avanti Research is a trademark of Avanti Polar Lipids, LLC

geralmente comprado junto com este produto

Nº do produto
Descrição
Preços

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number

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Sigma-Aldrich

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Sigma-Aldrich

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Sigma-Aldrich

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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
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
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
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
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