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SML0541 Sigma-Aldrich

7α,25-Dihydroxycholesterol

≥98% (HPLC)

Synonym: 5-Cholesten-3β,7α,25-triol

  • CAS Number 64907-22-8

  • Empirical Formula (Hill Notation) C27H46O3

  • Molecular Weight 418.65

  •  MDL number MFCD20488904

  •  PubChem Substance ID 329825542

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cholesterol and Cholesterol Metabolism,
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).

Packaging

5, 25 mg in glass bottle

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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