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SML0541

Sigma-Aldrich

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
MDL number:
MFCD20488904
UNSPSC Code:
12352211
PubChem Substance ID:
329825542
NACRES:
NA.77

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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.
Immunology, 70(3), 344-350 (1990-07-01)
Oxygenated derivatives of cholesterol are potent immunosuppressors. It has been reported previously that 7,25-dihydroxycholesterol (7,25-OHC), synthesized in the URA31, strongly inhibits the early steps of T-cell activation. So far, the mechanisms underlying this type of effect have been mainly investigated
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
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