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About This Item
Empirical Formula (Hill Notation):
C27H46O3
CAS Number:
Molecular Weight:
418.65
MDL number:
UNSPSC Code:
12352211
NACRES:
NA.25
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
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
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
InChI key
BQMSKLCEWBSPPY-IKVTXIKFSA-N
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
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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