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Merck
CN

SML0541

7α,25-Dihydroxycholesterol

≥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

Key Documents

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Product Name

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

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 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

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

2-8°C

Quality Level

100

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000482741
0000482741
0000377517
0000377517
0000374986

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Y H Ji et al.
Cancer biochemistry biophysics, 11(1), 45-57 (1990-01-01)
The antitumor effects of two new hydrosoluble derivatives of oxygenated sterols: JB69 and JC40 have been evaluated in vitro on a panel of lymphoma and leukemia cells from human and murine origins. These compounds result from the combination of a
C Moog et al.
Biochimie, 73(10), 1321-1326 (1991-10-01)
Oxysterols exhibit a wide variety of biological activities, including potent immunosuppressive effects. 7 beta,25-Dihydroxycholesterol (7,25-OHC), a synthetic oxysterol, has been shown to strongly inhibit the lymphocyte response to different stimuli. This compound has been chosen as a model compound to
C Moog et al.
International journal of immunopharmacology, 10(5), 511-518 (1988-01-01)
Several oxysterols are powerful immunosuppressors. Among them 7,25-dihydroxycholesterol (7,25-OHC) seems to be particularly interesting. The effect of this synthetic sterol on murine lymphocytes, stimulated by Con A, or by allogeneic or TNP-modified syngeneic lymphocytes, was investigated. The results showed that
Norman B Javitt
Current opinion in lipidology, 18(3), 283-288 (2007-05-15)
Recent findings extend the biologic activities of oxysterols as ligands for nuclear receptors to a role in morphogenesis during fetal development and to a role in the metabolism of photooxidation products of cholesterol in the retina. A 1000-fold increase of
C Moog et al.
Anticancer research, 13(4), 953-958 (1993-07-01)
New water soluble derivatives of oxysterols--the phosphodiesters of oxysterols and of nucleosides--have been synthesized. In vitro, these compounds share the biological properties of their parent oxysterols. Furthermore, they display anticancer activity when injected i.p. in mice bearing experimental tumors. The
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