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] An oxysterol signaling pathway mediated by the nuclear receptor LXR7alpha
[2] HOA TON KHA. Oxysterols Regulate Differentiation of Mesenchymal Stem Cells: Pro-Bone and Anti-Fat†[J]. Journal of Bone and Mineral Research, 2009, 19 5: 830-840. DOI:10.1359/jbmr.040115
[3] WOO-KYUN KIM. Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells[J]. Journal of Bone and Mineral Research, 2010, 25 4: 782-795. DOI:10.1359/jbmr.091024
[4] JENNIFER R DWYER. Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells.[J]. The Journal of Biological Chemistry, 2007, 282 12: 8959-8968. DOI:10.1074/jbc.m611741200
[5] DANIEL NEDELCU. Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling[J]. Nature chemical biology, 2013, 9 9: 557-564. DOI:10.1038/nchembio.1290
[6] YU-SHIUAN CHENG. A proteome-wide map of 20(S)-hydroxycholesterol interactors in cell membranes[J]. Nature chemical biology, 2021, 17 12: 1271-1280. DOI:10.1038/s41589-021-00907-2

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