4-hydroxy-3-[1-(4-hydroxyphenyl)-3-oxobutyl]-2H-chromen-2-one

• ChemBase ID: 154337
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: CC(=O)CC(c1ccc(cc1)O)c1c(c2ccccc2oc1=O)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cccc2)c1ccc(cc1)O
• InChI: InChI=1S/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/h2-9,15,21-22H,10H2,1H3
• InChIKey: RRZWAMPDGRWRPF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[1-(4-hydroxyphenyl)-3-oxobutyl]-2H-chromen-2-one
• IUPAC Traditional name: 4-hydroxy-3-[1-(4-hydroxyphenyl)-3-oxobutyl]chromen-2-one
• Synonyms: 4-Hydroxy-3-[1′-(4′′-hydroxyphenyl)-3′-oxobutyl]-2H-1-benzopyran-2-one; 4-Hydroxywarfarin; 4-Hydroxy-3-[1-(4-hydroxyphenyl)-3-oxobutyl]-2H-1-benzopyran-2-one; 3-(α-Acetonyl-p-hydroxybenzyl)-4-hydroxycoumarin; 4'-Hydroxy Warfarin

Database IDs

• CAS Number: 24579-14-4
• MDL Number: MFCD00272666
• PubChem SID: 162248476
• PubChem CID: 54682146

CALCULATED PROPERTIES

• Acid pKa: 6.157821
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.35496
• LogD (pH = 7.4): 1.1826483
• Log P: 2.441142
• Molar Refractivity: 88.841 cm^3
• Polarizability: 33.95315 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid; off-white
• Melting Point: 205-208°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C19H16O5

DETAILS

Sigma Aldrich - UC209

Biochem/physiol Actions
Minor CYP3A4 metabolite od (S)-warfarin.

Toronto Research Chemicals - H996100

A metabolite of Warfarin (W498500) in humans.

REFERENCES

• Barbato, F., et al.: J. Pharm. Sci., 86, 225 (1997)
• Kavana, M., et al.: Biochemistry, 42, 10238 (1997)
• Franco, A., et al.: Environ. Toxicol. Chem., 28, 458 (1997)