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| | 20ALPHA-HYDROXYCHOLESTEROL Basic information |
| Product Name: | 20ALPHA-HYDROXYCHOLESTEROL | | Synonyms: | 20alpha-Hydroxycholesterol (not deuterated);5-Cholestene-3B,20a-diol;Cholest-5-ene-3,20-diol, (3.beta.)-;5-cholestene-3β,20α-diol;(3S,8S,9S,10R,13S,14S,17S)-17-[(2R)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol;20α-Hydroxycholesterol (not deuterated);(20S)-Cholest-5-ene-3,20-diol;(3)-Cholest-5-ene-3,20-diol | | CAS: | 516-72-3 | | MF: | C27H46O2 | | MW: | 402.65 | | EINECS: | | | Product Categories: | Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids;Standards - 13C & 2H for GC-Mass Spectrometry | | Mol File: | 516-72-3.mol |  |
| | 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. | | pka | 15.04±0.70(Predicted) | | form | neat | | 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. |
| | 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 |
| | 20ALPHA-HYDROXYCHOLESTEROL Preparation Products And Raw materials |
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