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SML0541

Sigma-Aldrich

7α,25-Dihydroxycholesterol

≥98% (HPLC)

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Synonym(s):
5-Cholesten-3β,7α,25-triol
Empirical Formula (Hill Notation):
C27H46O3
CAS Number:
Molecular Weight:
418.65
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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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This Item
H1015SML1648128136
7α,25-Dihydroxycholesterol ≥98% (HPLC)

SML0541

7α,25-Dihydroxycholesterol

25-Hydroxycholesterol ≥98%

H1015

25-Hydroxycholesterol

Sigma-Aldrich

SML1648

24(S)-Hydroxycholesterol

7α, 25-dihydroxycholesterol

128136

7α, 25-dihydroxycholesterol

assay

≥98% (HPLC)

assay

≥98%

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

-

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

room temp

storage temp.

−20°C

storage temp.

−20°C

solubility

DMSO: 5 mg/mL (clear solution)

solubility

-

solubility

DMSO: 3 mg/mL, clear (warmed)

solubility

DMSO: 25 mg/mL

color

white to beige

color

-

color

white to beige

color

white

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Cholesterol powder, BioReagent, suitable for cell culture, ≥99%

Sigma-Aldrich

C3045

Cholesterol

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
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
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.
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
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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