SML0541

7α,25-Dihydroxycholesterol

≥98% (HPLC), powder, GPR183 agonist

• Synonym(s): 5-Cholesten-3β,7α,25-triol
• Empirical Formula (Hill Notation): C₂₇H₄₆O₃
• CAS Number: 64907-22-8
• Molecular Weight: 418.65
• MDL number: MFCD20488904
• UNSPSC Code: 12352211
• PubChem Substance ID: 329825542
• NACRES: NA.77

Properties

• Product Name: 7α,25-Dihydroxycholesterol, ≥98% (HPLC)
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 5 mg/mL (clear solution)
• storage temp.: 2-8°C
• SMILES string: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
• 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

Description

Application

7α,25-Dihydroxycholesterol has been used as a ligand for G protein-coupled receptor 183 (Gpr183).[1]

Biochem/physiol Actions

7α,25-Dihydroxycholesterol (7α,25-OHC) is a potent and selective endogenous ligand for the orphan GPCR receptor EBI2 (GPR183) with an EC₅₀ value in the picomolar range. The newly discovered EBI2–oxysterol signalling pathway has been shown to have an important role in the adaptive immune response, including a role in driving immune cell migration. In vitro and in vivo studies showed that 7,25-OHC can serve as a chemokine directing migration of B cells, T cells and dendritic cells.

7α,25-Dihydroxycholesterol has an ability to block the early steps of T-cell activation.[2]

7α,25-Dihydroxycholesterol is a potent agonist of the orphan GPCR receptor EBI2 (GPR183); directs immune cell migration.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable