20(S)-Hydroxycholesterol

Pricing Availability Delivery Time Qty
Cat.No. 4474 - 20(S)-Hydroxycholesterol | C27H46O2 | CAS No. 516-72-3
Description: Allosteric activator of Hedgehog (Hh) signaling; induces Smo accumulation
Chemical Name: (3β)-Cholest-5-ene-3,20-diol
Purity: ≥95%
Datasheet
Citations
Literature

Biological Activity

Allosteric activator of the Hedgehog signaling pathway Smoothened (Smo) oncoprotein; binds at a site distinct from the canonical cyclopamine binding site. Activates Hedgehog (Hh) signaling (EC50 ~ 3μM for induction of Hh reporter gene transcription in in NIH 3T3 cells). Induces Smo accumulation in primary cilia; also exhibits osteogenic activity and activates the liver X receptor (LXR).

Technical Data

M. Wt 402.65
Formula C27H46O2
Storage Store at -20°C
Purity ≥95%
CAS Number 516-72-3
PubChem ID 440711
InChI Key MCKLJFJEQRYRQT-MGNSQDQZSA-N
Smiles O[C@H](C4)CC[C@@]1(C)C4=CC[C@]2([H])[C@@]([H])1CC[C@@]3(C)[C@]([H])2CC[C@@]([H])3[C@](C)(O)CCCC(C)C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 40.26 100

Preparing Stock Solutions

The following data is based on the product molecular weight 402.65. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.48 mL 12.42 mL 24.84 mL
5 mM 0.5 mL 2.48 mL 4.97 mL
10 mM 0.25 mL 1.24 mL 2.48 mL
50 mM 0.05 mL 0.25 mL 0.5 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Nachtergaele et al (2012) Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat.Chem.Biol. 8 211 PMID: 22231273

Dwyer et al (2007) Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells J.Biol.Chem. 282 8959 PMID: 17200122

Nedelcu et al (2013) Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat.Chem.Biol. 9 557 PMID: 23831757


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Citations for 20(S)-Hydroxycholesterol

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Stem Cells Scientific Review

Written by Kirsty E. Clarke, Victoria B. Christie, Andy Whiting and Stefan A. Przyborski, this review provides an overview of the use of small molecules in the control of stem cell growth and differentiation. Key signaling pathways are highlighted, and the regulation of ES cell self-renewal and somatic cell reprogramming is discussed. Compounds available from Tocris are listed.

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