37826-48-5

Basic information

• Product Name: N-[[10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]amino]-4-methyl-benzenesulfonamide
• CAS NO: 37826-48-5
• Molecular Formula: C₃₄H₅₄N₂O₂S
• Molecular Weight: 554.881
• Mol File: 37826-48-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-[[10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]amino]-4-methyl-benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[[10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]amino]-4-methyl-benzenesulfonamide(37826-48-5)
• EPA Substance Registry System: N-[[10,13-dimethyl-17-(6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ylidene]amino]-4-methyl-benzenesulfonamide(37826-48-5)

Safety Data

• Hazardous Substances Data: 37826-48-5(Hazardous Substances Data)

Upstream product

• 15600-08-5 cholestan-3-one 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 15600-08-5 cholestan-3-one 
• 481-20-9 cholestane 
• 49661-14-5 Cholestan-3-on-N_.N-ditosylhydrazon 

Relevant articles and documents

Chemical Bypass of General Base Catalysis in Hedgehog Protein Cholesterolysis Using a Hyper-Nucleophilic Substrate

Proteins in the hedgehog family undergo self-catalyzed endoproteolysis involving nucleophilic attack by a molecule of cholesterol. Recently, a conserved aspartate residue (D303, or D46) of hedgehog was identified as the general base that activates cholesterol during this unusual autoprocessing event; mutation of the catalyzing functional group (D303A) reduces activity by >104-fold. Here we report near total rescue of this ostensibly dead general base mutant by a synthetic substrate, 3β-hydroperoxycholestane (3HPC) in which the sterol-OH group is replaced by the hyper nucleophilic-OOH group. Other hedgehog point mutants at D303, also unreactive with cholesterol, accepted 3HPC as a substrate with the rank order: WT > D303A ～D303N D303R, D303E. We attribute the revived activity with 3-HPC to the α-effect, where tandem electronegative atoms exhibit exceptionally high nucleophilicity despite relatively low basicity.