20(S)-Hydroxycholesterol

Names

[ CAS No. ]:
516-72-3

[ Name ]:
20(S)-Hydroxycholesterol

[Synonym ]:
20α-Hydroxy Cholesterol
20ALPHA-HYDROXYCHOLESTEROL

Biological Activity

[Description]:

20(S)-hydroxyCholesterol (20α-Hydroxycholesterol) is an allosteric activator of the oncoprotein smoothened (Smo) that activates the hedgehog (Hh) signaling pathway with an EC50 of 3 μM in a gene transcription reporter assay using NIH3T3 cells[1][2].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> Smo

Research Areas >> Cancer

[Target]

EC50: 3 μM (hedgehog signaling pathway)[1]

[References]

[1]. Nachtergaele S, et al. Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat Chem Biol. 2012 Jan 8;8(2):211-20.

[2]. Nedelcu D, et al, Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat Chem Biol. 2013 Sep;9(9):557-64.

Chemical & Physical Properties

[ Density]:
1.03g/cm3

[ Boiling Point ]:
512.3ºC at 760mmHg

[ Melting Point ]:
136-137ºC

[ Molecular Formula ]:
C₂₇H₄₆O₂

[ Molecular Weight ]:
402.65

[ Flash Point ]:
213.1ºC

[ Exact Mass ]:
402.35000

[ PSA ]:
40.46000

[ LogP ]:
6.50360

[ Index of Refraction ]:
1.538

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

In vitro osteoinductive effects of hydroxycholesterol on human adipose-derived stem cells are mediated through the hedgehog signaling pathway.

Plast. Reconstr. Surg. 134(5) , 960-8, (2014)

Human adipose-derived stem cells have been identified as a potential source of cells for use in bone tissue engineering because of their ready availability, ease of harvest, and susceptibility to oste...

Conversion of exogenous cholesterol into glycoalkaloids in potato shoots, using two methods for sterol solubilisation.

PLoS ONE 8 , e82955, (2013)

Steroidal glycoalkaloids (SGA) are toxic secondary metabolites naturally occurring in the potato, as well as in certain other Solanaceous plant species, such as tomato, eggplant and pepper. To investi...

Oxpholipin 11D: an anti-inflammatory peptide that binds cholesterol and oxidized phospholipids.

PLoS ONE 5 , e10181, (2010)

Many gram-positive bacteria produce pore-forming exotoxins that contain a highly conserved, 12-residue domain (ECTGLAWEWWRT) that binds cholesterol. This domain is usually flanked N-terminally by argi...