4,6-dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one

• ChemBase ID: 154338
• Molecular Formular: C19H16O5
• Molecular Mass: 324.32734
• Monoisotopic Mass: 324.09977361
• SMILES: CC(=O)CC(c1ccccc1)c1c(c2cc(ccc2oc1=O)O)O
• Canonical SMILES: CC(=O)CC(c1c(=O)oc2c(c1O)cc(cc2)O)c1ccccc1
• InChI: InChI=1S/C19H16O5/c1-11(20)9-14(12-5-3-2-4-6-12)17-18(22)15-10-13(21)7-8-16(15)24-19(17)23/h2-8,10,14,21-22H,9H2,1H3
• InChIKey: IQWPEJBUOJQPDE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,6-dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one
• IUPAC Traditional name: 4,6-dihydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
• Synonyms: 4,6-Dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one; 3-(α-Acetonylbenzyl)-4,6-dihydroxycoumarin; 6-Hydroxy Warfarin; 3-(α-Acetonylbenzyl)-4,6-dihydrocoumarin; 4-6-Dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one; 6-Hydroxywarfarin

Database IDs

• CAS Number: 17834-02-5
• MDL Number: MFCD00272665
• PubChem SID: 162248477
• PubChem CID: 54682459

CALCULATED PROPERTIES

• Acid pKa: 5.954644
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.3106956
• LogD (pH = 7.4): 0.9967442
• 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
• Apperance: Off-White to Pale Brown Solid; white
• Melting Point: 119-120 °C; 200-204°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 - UC208

Biochem/physiol Actions
CYP1A2/2C9 metabolite of (R)-warfarin

Toronto Research Chemicals - H996120

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)