25-Hydroxycholesterol

Names

[ Name ]:
25-Hydroxycholesterol

[Synonym ]:
25-Hydroxy Cholesterol
(3β,9β,14β)-Cholest-5-ene-3,25-diol
Cholest-5-ene-3,25-diol, (3β,9β,14β)-
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

Biological Activity

[Description]:

25-Hydroxycholesterol is a metabolite of cholesterol that is produced and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-hydroxycholesterol is a potent (EC50≈65 nM) and selective suppressor of IgA production by B cells.

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Natural Products >> Steroids

[Target]

Human Endogenous Metabolite

[In Vitro]

The synthesis of 25-hydroxycholesterol is catalyzed by the enzyme cholesterol 25-hydroxylase, which uses cholesterol and molecular oxygen as substrates and NADPH as a cofactor. 25-hydroxycholesterol is a potent bioactive lipid in the innate and adaptive immune systems[1].

[References]

[1]. McDonald JG, et al. Editorial: 25-Hydroxycholesterol: a new life in immunology. J Leukoc Biol. 2010 Dec;88(6):1071-2.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
513.1±23.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₇H₄₆O₂

[ Molecular Weight ]:
402.653

[ Flash Point ]:
213.5±17.2 °C

[ Exact Mass ]:
402.349792

[ PSA ]:
40.46000

[ LogP ]:
7.66

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.538

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H315-H319-H332-H335-H373

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
20/21/22-36/37/38-48

[ Safety Phrases ]:
26-36-45

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Articles

Oxysterols synergize with statins by inhibiting SREBP-2 in ovarian cancer cells.

Gynecol. Oncol. 135(2) , 333-41, (2014)

Determine mechanisms responsible for enhanced statin efficacy in a novel statin combination we name STOX (STatin-OXysterol).Ovarian cancer cell lines were treated with combinations of statins and oxys...

The effects of Zanthoxylum bungeanum extract on lipid metabolism induced by sterols.

J. Pharmacol. Sci. 127(3) , 251-9, (2015)

Variant pharmacological activities of Zanthoxylum bungeanum were determined before. The aim of this study was to assess whether Z. bungeanum could regulate lipid metabolism. The cholesterol overloadin...

Specific cellular incorporation of a pyrene-labelled cholesterol: lipoprotein-mediated delivery toward ordered intracellular membranes.

PLoS ONE 10(4) , e0121563, (2015)

In the aim of testing tools for tracing cell trafficking of exogenous cholesterol, two fluorescent derivatives of cholesterol, 22-nitrobenzoxadiazole-cholesterol (NBD-Chol) and 21-methylpyrenyl-choles...

Related Compounds

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