20(S)-Hydroxycholesterol | Smoothened activator

CAS:
516-72-3
Catalog Number:
10-4540
Activity:
Smoothened activator
Chemical Name:
5-Cholesten-3β, 20α-diol
Molecular Weight:
402.66
Molecular Formula:
C27H46O2
Solubility:
Soluble in DMSO or in Ethanol.
Physical Properties:
White solid
Purity:
98% by TLC
NMR (Conforms)
Storage Temperature:
-20°
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.
Shipping Code:
RT

Available Options

Size :PriceQuantity 
1 mg$40.00
5 mg$90.00

20(S)-Hydroxycholesterol (516-72-3) is an endogenous ligand for the LXR receptor.1 It has anti-adipogenic and pro-osteogenic effects in mesenchymal stem cells mediated via a non-LXR dependent pathway.2 The osteogenic effects of 20-(S)-hydroxycholesterol have been shown to be mediated by activation of hedgehog signaling and expression of genes associated with Notch signaling.3 Activation of Hedgehog is mediated via binding of 20(S)-hydroxycholesterol to Smoothened at a site distinct from the cyclopamine binding site.4,5 It has also been found to be an endogenous ligand for the sigma 2 receptor.6

References/Citations:

1) Janowski et al. (1996), An oxysterol signaling pathway mediated by the nuclear receptor LXR7alpha; Nature383 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

CAS:
516-72-3
Catalog Number:
10-4540
Activity:
Smoothened activator
Chemical Name:
5-Cholesten-3β, 20α-diol
Molecular Weight:
402.66
Molecular Formula:
C27H46O2
Solubility:
Soluble in DMSO or in Ethanol.
Physical Properties:
White solid
Purity:
98% by TLC
NMR (Conforms)
Storage Temperature:
-20°
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.
Shipping Code:
RT

Safety Data Sheet:

Product Data Sheet:

Materials provided by Focus Biomolecules are for laboratory research use only and are not intended for human or veterinary applications. Please note that we do not sell to individuals and that all orders placed by non-research organizations will incur a $20 restocking/refund fee