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Merck
CN

700080P

Avanti

7α,25-dihydroxycholesterol

Avanti Research™ - A Croda Brand

Synonym(s):

cholest-5-ene-3β,7α,25-triol

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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.25

Key Documents

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InChI key

BQMSKLCEWBSPPY-IKVTXIKFSA-N

InChI

1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

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

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (700080P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

shipped in

dry ice

storage temp.

−20°C

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General description

7α,25-dihydroxycholesterol (7α,25-OHC) is synthesized by the hydroxylation of cholesterol by the action of enzyme cholesterol 25-hydroxylase (CH25H) and cytochrome P450, family 7, subfamily b, polypeptide 1 (CYP7B1). The catabolic breakdown of 7α,25-OHC to bile acid precursors is catalyzed by the enzymes hydroxy-Δ-5-steroid dehydrogenase, 3β- and steroid Δ-isomerase 7 (HSD3B7).

Application

7α,25-dihydroxycholesterol has been used:
  • as a G-protein-coupled receptor 183 ( GPR183) ligand in chemotaxis assay and intracellular cytokine staining method and in fluorescence-activated cell sorting (FACS) analysis of natural killer cells
  • in oxysterol based calcium mobilization assay in Chinese hamster ovary (CHO) cells
  • in competitive radioligand binding assay of Epstein-Barr virus-induced gene 2 (EBI2) expressing COS-7 cells

Biochem/physiol Actions

7α,25-dihydroxycholesterol (7α,25-OHC) serves as an endogenous ligand for G-protein-coupled receptor 183 (GPR183) or Epstein-Barr virus-induced gene 2 (EBI2). It plays a key role in the migration of type 3 innate lymphoid cells (ILC3) in the small intestine and colon. 7α,25-OHC mediates immune cell migration functionality by their chemoattractant property. Inhibition of 7α,25-OHC synthesis leads to impairment in the migration of B cells.

Packaging

5 mL Amber Glass Screw Cap Vial (700080P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Gene regulatory programs conferring phenotypic identities to human NK cells
Collins PL, et al.
Cell, 176(1-2), 348-360 (2019)
Oxysterol sensing through the receptor GPR183 promotes the lymphoid-tissue-inducing function of innate lymphoid cells and colonic inflammation
Emgaard J, et al.
Immunity, 48(1), 120-132 (2018)
Identification of structural motifs critical for epstein-barr virus-induced molecule 2 function and homology modeling of the ligand docking site
Zhang L, et al.
Molecular Pharmacology, 82(6), 1094-1103 (2012)
Katharina R Beck et al.
The Journal of steroid biochemistry and molecular biology, 190, 19-28 (2019-03-25)
Oxysterols are cholesterol metabolites derived through either autoxidation or enzymatic processes. They consist of a large family of bioactive lipids that have been associated with the progression of multiple pathologies. In order to unravel (patho-)physiological mechanisms involving oxysterols, it is

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