4-hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]-2H-chromen-2-one

• ChemBase ID: 154382
• Molecular Formular: C19H16O4
• Molecular Mass: 308.32794
• Monoisotopic Mass: 308.10485899
• SMILES: CC(=O)C[C@H](c1ccccc1)c1c(c2ccccc2oc1=O)O
• Canonical SMILES: CC(=O)C[C@@H](c1c(=O)oc2c(c1O)cccc2)c1ccccc1
• InChI: InChI=1S/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3/t15-/m1/s1
• InChIKey: PJVWKTKQMONHTI-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]-2H-chromen-2-one
• IUPAC Traditional name: warfarin
• Synonyms: 4-Hydroxy-3-[(1R)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-2-one; R-(+)- 3-(α-Acetonylbenzyl)-4-hydroxycoumarin; (+)-Warfarin; (R)-Warfarin; Dextrowarfarin; R-(+)-Warfarin; R-(+)-3-Acetonybenzyl)-4-hydroxycoumarin; R-(+)-4-Hydroxy-3-(3-oxo-1-phenybutyl)-2H-1-benzopyran-2-one; (R)-(+)-Warfarin

Database IDs

• CAS Number: 5543-58-8
• EC Number: 226-908-9
• MDL Number: MFCD00272376
• PubChem SID: 24724649; 162248521
• PubChem CID: 54684598

CALCULATED PROPERTIES

• Acid pKa: 6.330688
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.6849828
• LogD (pH = 7.4): 1.6473457
• Log P: 2.7447073
• Molar Refractivity: 86.8601 cm^3
• Polarizability: 33.339684 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid; white to pale yellow
• Melting Point: ≥170 °C; 170-172°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 61-48/25-52/53
• Safety Statements: 53-45-61
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360D-H372-H412
• GHS Precautionary statements: P201-P273-P308 + P313
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CYP2C9(1559)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C19H16O4

DETAILS

Sigma Aldrich - UC213

Biochem/physiol Actions
CYP1A2/3A4 substrate; anticoagulant.

Toronto Research Chemicals - W498490

The R-(+)-form of Warfarin (W498500). Coumarin anticoagulant.

REFERENCES

• Hagan, E.C., et al.: J. Am. Pharm. Assoc. Sci. Ed., 42, 379 (1953)
• Bell, R.G., et al.: Biochemistry, 11, 1959 (1953)
• Valente, J.E., et al.: J. Med. Chem., 20, 1489 (1953)
• Back, N., et al.: Pharmacol. Res. Commun., 10, 445, (1953)
• Babhair, S.A., et al.