516-72-3

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 NO: 516-72-3
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.65
• Product Categories: Standards - 13C & 2H for GC-Mass Spectrometry;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 516-72-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 136-137°C
• Boiling Point: 512.3°Cat760mmHg
• Flash Point: 213.1°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 1.23E-12mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: -20°C Freezer
• Solubility: Soluble in DMSO or in Ethanol.
• PKA: 15.04±0.70(Predicted)
• 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.
• CAS DataBase Reference: 20ALPHA-HYDROXYCHOLESTEROL(CAS DataBase Reference)
• NIST Chemistry Reference: 20ALPHA-HYDROXYCHOLESTEROL(516-72-3)
• EPA Substance Registry System: 20ALPHA-HYDROXYCHOLESTEROL(516-72-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 516-72-3(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 516-72-3 differently. You can refer to the following data:
1. A metabolite of Cholesterol. Cholesterol oxidation product having cytotoxicity effects
2. A metabolite of Cholesterol (C432501). Cholesterol oxidation product having
3. 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.

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

InChI:InChI=1/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1

Upstream product

• 1778-02-5 Pregnenolone acetate 
• 7429-94-9 isohexylmagnesium bromide 
• 57-88-5 cholesterol 
• 108354-83-2 20-ξ-hydroxy-23-oxocholest-5-en-3β-yl p-bromobenzoate 
• 24336-13-8 6β,20α-Dihydroxy-3α,5-cyclo-5α-cholestan 
• 58701-45-4 3β-t-butyldimethylsilyloxy-pregn-5-en-20-one 
• 626-88-0 1-bromo-5-methylpentane 
• 15387-47-0 3α,5-cyclo-5α-pregnan-6β-ol-20-one 
• 145-13-1 Pregnenolone 
• 115910-64-0 (20R)-3β-(tert-butyldimethylsilyl)oxycholest-5-en-22-yn-20-ol 
• 7154-75-8 4-methylpentyne 
• 604-32-0 cholesteryl benzoate 
• 26048-47-5 5α,6β-dibromocholestan-3β-yl benzoate 

Downstream Products

• 24339-15-9 3,6-Dioxo-20α-hydroxy-5α-cholestan 
• 145-13-1 Pregnenolone 

Relevant articles and documents

Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst

Seven mono-and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3 )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.

Glucal-conjugated sterols as novel vascular leakage blocker: Structure-activity relationship focusing on the C17-side chain

A series of glucal-conjugated sterols as novel vascular leakage blocker were identified through design, synthesis and biologically evaluation. In addition, the structure-activity relationship (SAR) of the glucal-conjugated sterols focusing on the C17-side chain was also established. The sterol analogs linked with the rigid C17-side chain side chains exhibited potent cell survival activities. In particular, analog 21l, which possesses a cyclopentyl oxime moiety, was shown to have excellent pharmacological effects on retinal vascular leakage in a diabetic mouse model.

NOVEL VASCULAR LEAK INHIBITOR

The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present disclosure inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, enhances the cortical actin ring structure, and improves the stability of the tight junctions (TJs) between vascular cells, thereby inhibiting vascular leakage. The vascular leakage inhibitor of the present disclosure has the activity of not only reducing vascular permeability but also recovering the integrity of damaged blood vessels. Accordingly, the vascular leakage inhibitor of the present disclosure can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present disclosure is synthesized from commercially available or easily synthesizable cholesterols, it has remarkably superior feasibility of commercial synthesis.