An allosteric Smo agonist
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20(S)-hydroxy Cholesterol

Item No. 20103

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cholest-5-ene-3β,20-diol
CAS Number
516-72-3
Synonyms
  • 20α-hydroxy Cholesterol
Molecular Formula
C27H46O2
Formula Weight
402.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mLDMSO: 0.1 mg/mLEthanol: 20 mg/mLEthanol:PBS (pH 7.2)(1:2): 0.3 mg/mL
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@](O)(C)CCCC(C)C
InChi Code
InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChi Key
MCKLJFJEQRYRQT-APGJSSKUSA-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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    Product Description

    20(S)-hydroxy Cholesterol is an allosteric agonist of the smoothened (Smo) receptor that activates the hedgehog (Hh) signaling pathway with an EC50 value of approxiately 3 μM in a gene transcription reporter assay using NIH3T3 cells.1 20(S)-hydroxy Cholesterol is necessary for normal Hh signaling. It induces Smo accumulation in primary cilia, an early event in signaling, and binds to the extracellular, cysteine-rich domain of Smo.1,2 20(S)-hydroxy Cholesterol also stimulates osteogenic differentiation of pluripotent bone marrow stromal cells, a process mediated via Hh and Notch signaling.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nachtergaele, S., Mydock, L.K., Krishnan, K., et al. Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat. Chem. Biol. 8(2), 211-220 (2012).

    2. Nedelcu, D., Liu, J., Xu, Y., et al. Oxysterol binding to the extracellular domain of smoothened in hedgehog signaling. Nat. Chem. Biol. 9(9), 557-564 (2013).

    3. Kha, H.T., Basseri, B., Shouhed, D., et al. Oxysterols regulate differentiation of mesenchymal stem cells: Pro-bone and anti-fat. J. Bone Miner. Metab. 19(5), 830-840 (2004).

    4. Dwyer, J.R., Sever, N., Carlson, M., et al. Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells. The Journal of Biological Chemisty 282(12), 8959-8968 (2007).

    5. Kim, W.-K., Meliton, V., Tetradis, S., et al. Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells. J. Bone Miner. Metab. 25(4), 782-795 (2010).