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.

Product information

CAS Number: 516-72-3

Molecular Weight: 402.65

Formula: C27H46O2

Synonym:

20α-Hydroxycholesterol

Chemical Name: (1S, 3aS, 3bS, 7S, 9aR, 9bS, 11aS)-1-[(2S)-2-hydroxy-6-methylheptan-2-yl]-9a, 11a-dimethyl-1H, 2H, 3H, 3aH, 3bH, 4H, 6H, 7H, 8H, 9H, 9aH, 9bH, 10H, 11H, 11aH-cyclopenta[a]phenanthren-7-ol

Smiles: CC(C)CCC[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C

InChiKey: MCKLJFJEQRYRQT-APGJSSKUSA-N

InChi: InChI=1S/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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 30 mg/mL (74.51 mM; ultrasonic and warming and heat to 60°C)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

References:

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

Products are for research use only. Not for human use.