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Merck
CN

128136

7α, 25-dihydroxycholesterol

Synonym(s):

7α, 25-dihydroxycholesterol, EBI2 agonist, EBI2 Activator, GPR183 Activator, 7alpha,25-OHC

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About This Item

Empirical Formula (Hill Notation):
C27H46O3
CAS Number:
64907-22-8
Molecular Weight:
418.65
MDL number:
MFCD20488904
UNSPSC Code:
12352211
NACRES:
NA.77

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InChI key

BQMSKLCEWBSPPY-IKVTXIKFSA-N

SMILES string

O[C@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCCC(O)(C)C)C)(CC[C@@H]2[C@]4(CC[C@@H](CC4=C1)O)C)C

assay

≥98% (HPLC)

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 25 mg/mL

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Disclaimer

Toxicity: Standard Handling (A)

General description

A highly potent and specific oxysterol EBI2 (GPR183) agonist with a kd of 450 pM in a saturation binding analysis, and activates EBI2 (EC50=140 pM compared with 2.1nM for its enantiomer 7b,25-OHC) in a GTP-γ assay. Dose-dependenty suppresses forskolin-induced cAMP accumulation in EBI2-expressing SK-N-MC/CRE-β galactosidase cell line with an IC50 of 2 nM, but not in control cells. Stimulates migration of LPS-activated spleen B cells and T cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells from EBI2-deficient mice.

Other Notes

Liu, C., et al. 2011. Nature475, 519.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C. Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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