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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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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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

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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
0000543094
0000539829
0000543094
0000482741
0000482741

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C Moog et al.
International journal of immunopharmacology, 11(5), 559-565 (1989-01-01)
The effects of an oxysterol, 7,25-dihydroxycholesterol (7,25-OHC), cyclosporin A (CsA) and dexamethasone (Dex) on the blastogenic response of murine lymphocytes to various stimuli were investigated. 7,25-OHC markedly depressed the response to Con A, anti-T3 monoclonal antibodies and to the combination
J Zhang et al.
Biochimica et biophysica acta, 1344(3), 241-249 (1997-02-18)
The metabolism of 25-hydroxycholesterol in different cell types was studied and the role of 7 alpha-hydroxylation for the effect of 25-hydroxycholesterol on the activity of HMG-CoA reductase was determined. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2
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
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.
Antiviral chemistry & chemotherapy, 9(6), 491-496 (1998-12-29)
Oxysterols, oxygenated derivatives of cholesterol selected for their cytostatic activity and their inhibitory effect on cholesterol synthesis, have been investigated for their anti-human immunodeficiency virus (HIV) activity in vitro. The three oxysterols tested, 7 beta-hydroxycholesterol (7 beta-OHC), 25-hydroxycholesterol (25-OHC) and
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Global Trade Item Number

SKUGTIN
SML0541-25MG04061833058374
SML0541-5MG04061833058381

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