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SML0541

7α,25-Dihydroxycholesterol

Name: 7&#945;,25-Dihydroxycholesterol
Brand: SIGMA

≥98% (HPLC), powder, GPR183 agonist

Synonym(s):

5-Cholesten-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

UNSPSC Code:

12352211

PubChem Substance ID:

329825542

NACRES:

NA.77

MDL number:

MFCD20488904

Assay:

≥98% (HPLC)

Form:

powder

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Properties

Product Name

7α,25-Dihydroxycholesterol, ≥98% (HPLC)

Quality Segment

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).

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.

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

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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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Global Trade Item Number

SKU	GTIN
SML0541-5MG	04061833058381
SML0541-25MG	04061833058374