20ALPHA-HYDROXYCHOLESTEROL Chemical Properties

Melting point:

136-137°C

Boiling point:

512.3±23.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in DMSO or in Ethanol.

form 

Solid

pka

15.04±0.70(Predicted)

color 

White

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

20ALPHA-HYDROXYCHOLESTEROL Usage And Synthesis

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. 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. 20(S)-hydroxy Cholesterol also stimulates osteogenic differentiation of pluripotent bone marrow stromal cells, a process mediated via Hh and Notch signaling.

Chemical Properties

White Solid

Uses

A metabolite of Cholesterol. Cholesterol oxidation product having cytotoxicity effects

Uses

A metabolite of Cholesterol (C432501). Cholesterol oxidation product having cytotoxicity effects.

Definition

ChEBI: An oxysterol that is cholesterol substituted by a hydroxy group at position 20.

storage

Store at -20°C

References

1) Janowski?et al. (1996),?An oxysterol signaling pathway mediated by the nuclear receptor LXR7alpha; Nature,?383?728 2) Kha?et al. (2004),?Oxysterols regulate differentiation of mesenchymal stem cells: Pro-bone and Anti-fat: J. Bone Min. Res.,?19?830 3) Kim?et al. (2010),?Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells; J. Bone Miner. Res.,?25?7823 4) Dwyer?et al. (2007),?Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells; J. Biol. Chem.,?282?8959 5) Nedelcu?et al. (2013);?Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling; Nat. Chem. Biol.,?9?557 6) Cheng?et al. (2021);?A proteome-wide map of 20(S)-hydroxycholesterol interactors in cell membranes; Nat. Chem. Biol.,?17?1271

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