20(S)-Hydroxycholesterol

Modify Date: 2024-01-19 00:33:10

20(S)-Hydroxycholesterol Structure
20(S)-Hydroxycholesterol structure
Common Name 20(S)-Hydroxycholesterol
CAS Number 516-72-3 Molecular Weight 402.65
Density 1.03g/cm3 Boiling Point 512.3ºC at 760mmHg
Molecular Formula C27H46O2 Melting Point 136-137ºC
MSDS Chinese USA Flash Point 213.1ºC

 Use of 20(S)-Hydroxycholesterol


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].

 Names

Name 20-hydroxycholesterol
Synonym More Synonyms

 20(S)-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
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

 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

 Articles29

More 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...

 Synonyms

20α-Hydroxy Cholesterol
20ALPHA-HYDROXYCHOLESTEROL