20(S)-Hydroxycholesterol

Name: 20( S )-Hydroxycholesterol
Brand: Tocris Bioscience
SKU: 4474

Tocris Bioscience, part of Bio-Techne | Catalog # 4474

Citations (8)

COA / SDS

Allosteric activator of Hedgehog (Hh) signaling; induces Smo accumulation

Key Product Details

Description:	Allosteric activator of Hedgehog (Hh) signaling; induces Smo accumulation
Chemical Name:	(3β)-Cholest-5-ene-3,20-diol
Purity:	≥95% (HPLC)
Molecular Weight:	402.65

View Full Technical Details for 20(S)-Hydroxycholesterol

Technical Data
Citations

Biological Activity for 20(S)-Hydroxycholesterol

20(S)-Hydroxycholesterol is an 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 for 20(S)-Hydroxycholesterol

M. Wt	402.65
Formula	C₂₇H₄₆O₂
Storage	Store at -20°C
Purity	≥95% (HPLC)
CAS Number	516-72-3
PubChem ID	440711
InChi Key	MCKLJFJEQRYRQT-APGJSSKUSA-N
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

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

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility for 20(S)-Hydroxycholesterol

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

Preparing Stock Solutions for 20(S)-Hydroxycholesterol

The following data is based on the product molecular weight 402.65.

Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	2.48 mL	12.42 mL	24.84 mL
5 mM	0.50 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	0.50 mL

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References for 20(S)-Hydroxycholesterol

References are publications that support the biological activity of the product.

Dwyer Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells J.Biol.Chem. 2007 PMID: 17200122
Nedelcu Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat.Chem.Biol. 2013 PMID: 23831757
Nachtergaele Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat.Chem.Biol. 2012 PMID: 22231273