24579-14-4

Basic information

• Product Name: 4-HYDROXY-3-[1'-(4''-HYDROXYPHENYL)-3'-OXOBUTYL]-2H-1-BENZOPYRAN-2-ONE
• Synonyms: 4-HYDROXYWARFARIN;4-HYDROXY-3-[1'-(4''-HYDROXYPHENYL)-3'-OXOBUTYL]-2H-1-BENZOPYRAN-2-ONE;4-Hydroxy-3-[1(4hydroxyphenl)-3oxobutyl]-2H-1-benzopyran-2-one;3-[α-(2-Oxopropyl)-4-hydroxybenzyl]-4-hydroxycoumarin;3-(α-Acetonyl-p-hydroxybenzyl)-4-hydroxycouMarin
• CAS NO: 24579-14-4
• Molecular Formula: C₁₉H₁₆O₅
• Molecular Weight: 324.33
• Product Categories: Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Aromatics;Heterocycles;Metabolites & Impurities
• Mol File: 24579-14-4.mol
• Article Data: 2

Chemical Properties

• Melting Point: 205-208°C
• Boiling Point: 522°Cat760mmHg
• Flash Point: 190.3°C
• Appearance: off-white/
• Density: 1.384g/cm³
• Vapor Pressure: 1E-11mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble
• CAS DataBase Reference: 4-HYDROXY-3-[1'-(4''-HYDROXYPHENYL)-3'-OXOBUTYL]-2H-1-BENZOPYRAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-[1'-(4''-HYDROXYPHENYL)-3'-OXOBUTYL]-2H-1-BENZOPYRAN-2-ONE(24579-14-4)
• EPA Substance Registry System: 4-HYDROXY-3-[1'-(4''-HYDROXYPHENYL)-3'-OXOBUTYL]-2H-1-BENZOPYRAN-2-ONE(24579-14-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 24579-14-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A minor CYP3A4 metabolite of S-Warfarin

InChI:InChI=1/C19H16O5/c1-11(20)10-15(12-6-8-13(21)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,21,23H,10H2,1H3

Upstream product

• 81-81-2 warfarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 22214-30-8 4-(4'-hydroxyphenyl)but-3-en-2-one 
• 129-06-6 warfarin 

Relevant articles and documents

Microbial models of mammalian metabolism: Conversion of warfarin to 4'-hydroxywarfarin using Cunninghamella bainieri

Warfarin, an anticoagulant and 'metabolic probe' for cytochrome P-450 isozyme multiplicity, is metabolized to 4'-hydroxywarfarin, a principle mammalian metabolite, using the fungus Cunninghamella bainieri (UI-3065). The metabolite was isolated from cell suspension cultures and characterized by analytical (TLC, HPLC, GC-MS) and spectral (HRMS, EI-MS, PMR) comparisons with authentic 4'-hydroxywarfarin. The mechanism of aromatic hydroxylation was examined in C. bainieri using 4'-deuterowarfarin. The absence of a primary isotope effect (K(H)/K(D) = 1.13), migration and retention of deuterium in the phenolic product [80% migration and retention (M&R)], and inhibition of the hydroxylation by carbon monoxide (93% inhibition in a 50:50 CO:O2 atmosphere) are consistent with a cytochrome P-450-mediated hydroxylation involving the classic NIH shift (arene oxide) pathway.