4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one

• ChemBase ID: 126912
• Molecular Formular: C14H12O3
• Molecular Mass: 228.24328
• Monoisotopic Mass: 228.07864424
• SMILES: O=c1oc(cc(OC)c1)/C=C/c1ccccc1
• Canonical SMILES: COc1cc(/C=C/c2ccccc2)oc(=O)c1
• InChI: InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3
• InChIKey: DKKJNZYHGRUXBS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one; 4-methoxy-6-[(E)-2-phenylethenyl]-2H-pyran-2-one
• IUPAC Traditional name: desmethoxyyangonin
• Synonyms: 5,6-Dehydrokawain; 4-methoxy-6-[(E)-2-phenylvinyl]-2-pyranone; Desmethoxyyangonin; Desmethoxyyangonin; 5,6-Dehydrokawain; 4-Methoxy-6-[(1E)-2-phenylethenyl]-2H-pyran-2-one; (E)-4-Methoxy-6-styryl-2H-pyran-2-one; 5,6-Dehydrokavain; Demethoxyyangonin; NSC 112161; NSC 68686; trans-5,6-Dehydrokawain; Desmethoxy Yangonin

Database IDs

• CAS Number: 15345-89-8
• PubChem SID: 162221238
• PubChem CID: 5273621
• CHEMBL: 254218
• Chemspider ID: 4438012
• Wikipedia Title: Desmethoxyyangonin

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.63949
• LogD (pH = 7.4): 2.63949
• Log P: 2.63949
• Molar Refractivity: 68.7407 cm^3
• Polarizability: 25.136261 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder; white to faint yellow powder
• Melting Point: 148°C
• Boiling Point: 440°C
• Density: 1.18 g/mL

DETAILS

Toronto Research Chemicals - D290670

The microsomal metabolite of Yangonin (Y100550).

REFERENCES

• Johnson, B., et al.: Chem. Res. Toxicol., 16, 733 (2003)
• Mathews, J., et al.: Drug Metab. Dispos., 33, 1555 (2003)
• Zou, L., et al.: Planta Medica, 71, 142 (2003)