(3β,7α)-Cholest-5-ene-3,7,25-triol

Names

[ Name ]:
(3β,7α)-Cholest-5-ene-3,7,25-triol

[Synonym ]:
Cholest-5-ene-3,7,25-triol, (3β,7α)-
7.α.,25-dihydroxy Cholesterol
(3β,7α)-Cholest-5-ene-3,7,25-triol

Biological Activity

[Description]:

7α, 25-dihydroxycholesterol (7α,25-OHC) is a potent and selective agonist and endogenous ligand of the orphan GPCR receptor EBI2 (GPR183). 7α, 25-dihydroxycholesterol is highly potent at activating EBI2 (EC50=140 pM; Kd=450 pM). 7α, 25-dihydroxycholesterol can serve as a chemokine directing migration of B cells, T cells and dendritic cells[1][2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> EBI2/GPR183

[Target]

Human Endogenous Metabolite

[In Vitro]

In vitro, 7α, 25-dihydroxycholesterol (7α,25-OHC) stimulates the migration of EBI2-expressing mouse B and T cells with half-maximum effective concentration values around 500 pM, but had no effect on EBI2-deficient cells[1].

[In Vivo]

EBI2-deficient B cells or normal B cells desensitized by 7α,25-Dihydroxycholesterol (1 μM; 1.5 hours) pre-treatment shows reduced homing to follicular areas of the spleen[1].

[References]

[1]. Liu C, et al. Oxysterols direct B-cell migration through EBI2. Nature. 2011 Jul 27;475(7357):519-23.

[2]. Hannedouche S, et al. Oxysterols direct immune cell migration via EBI2. Nature. 2011 Jul 27;475(7357):524-7.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
548.5±35.0 °C at 760 mmHg

[ Melting Point ]:
235 - 236 °C

[ Molecular Formula ]:
C₂₇H₄₆O₃

[ Molecular Weight ]:
418.652

[ Flash Point ]:
230.5±20.5 °C

[ Exact Mass ]:
418.344696

[ PSA ]:
60.69000

[ LogP ]:
5.75

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.550

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Articles

Detection of dihydroxycholesterols in human plasma using HPLC-ESI-MS/MS.

Steroids 99 , 131-8, (2015)

We report a straightforward sample preparation procedure and a direct liquid chromatography electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) method for the analysis of 7alpha,25-dihydro...

Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase.

Biochim. Biophys. Acta 1344(3) , 241-9, (1997)

The metabolism of 25-hydroxycholesterol in different cell types was studied and the role of 7 alpha-hydroxylation for the effect of 25-hydroxycholesterol on the activity of HMG-CoA reductase was deter...

Molecular characterization of oxysterol binding to the Epstein-Barr virus-induced gene 2 (GPR183).

J. Biol. Chem. 287(42) , 35470-83, (2012)

Oxysterols are oxygenated cholesterol derivates that are emerging as a physiologically important group of molecules. Although they regulate a range of cellular processes, only few oxysterol-binding ef...