A potent and selective agonist of GPR183
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7α,25-dihydroxy Cholesterol

Item No. 11032

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,7α)-cholest-5-ene-3,7,25-triol
CAS Number
64907-22-8
Synonyms
  • 7α,25-DHC
Molecular Formula
C27H46O3
Formula Weight
418.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 100 µg/mlEthanol: 2 mg/mlEthanol:PBS (pH 7.2)(1:2): 500 µg/ml
SMILES
O[C@@H]1C=C2C[C@@H](O)CC[C@]2(C)[C@]3([H])[C@]1([H])[C@@](CC[C@]4([H])[C@H](C)CCCC(C)(C)O)([H])[C@]4(C)CC3
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    Product Description

    GPR183 (also known as Epstein-Barr virus-induced gene 2) is an orphan G protein-coupled receptor (GPCR) that is highly expressed in spleen and is required for humoral immune responses, including B cell migration and T cell-dependent antibody production.1,2 7α,25-dihydroxy Cholesterol (7α,25-DHC) is a potent agonist of GPR183 that induces specific activation of the receptor with an EC50 value of 50 nM (Kd = 450 pM).1,2 At concentrations below 3 μM, it does not show any appreciable binding activity when tested against eight different nuclear hormone receptors including LXR and thirty-one different G protein-coupled receptors in a panel of reporter gene assays.2 7α,25-DHC can act as a potent chemokine, affecting migration of immune cells expressing GPR183 both in vitro (EC50 = 500 pM) and in vivo.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Liu, C., Yang, X.V., Wu, J., et al. Oxysterols direct B-cell migration through EB12. Nature 475(7357), 519-523 (2011).

    2. Hannedouche, S., Zhang, J., Yi, T., et al. Oxysterols direct immune cell migration via EBI2. Nature 475(7357), 524-527 (2011).

    Product Citations

    Cashikar, A.G., Toral-Rios, D., Timm, D., et al. Regulation of astrocyte lipid metabolism and ApoE secretionby the microglial oxysterol, 25-hydroxycholesterol. J. Lipid Res. 64(4), 100350 (2023).