methyl 2-[(2E)-3-hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene]-2-phenylacetate

• ChemBase ID: 179567
• Molecular Formular: C19H14O5
• Molecular Mass: 322.31146
• Monoisotopic Mass: 322.08412355
• SMILES: C1(=C(/C(=C(/c2ccccc2)\C(=O)OC)/OC1=O)O)c1ccccc1
• Canonical SMILES: COC(=O)/C(=C\1/OC(=O)C(=C1O)c1ccccc1)/c1ccccc1
• InChI: InChI=1S/C19H14O5/c1-23-18(21)15(13-10-6-3-7-11-13)17-16(20)14(19(22)24-17)12-8-4-2-5-9-12/h2-11,20H,1H3/b17-15+
• InChIKey: OMZRMXULWNMRAE-BMRADRMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-[(2E)-3-hydroxy-5-oxo-4-phenyl-2,5-dihydrofuran-2-ylidene]-2-phenylacetate
• IUPAC Traditional name: methyl 2-[(2E)-3-hydroxy-5-oxo-4-phenylfuran-2-ylidene]-2-phenylacetate
• Synonyms: Vulpinic Acid; (αE)-α-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)benzeneacetic Acid Methyl Ester; 3,4-Dihydroxy-2,5-Diphenyl-2,4-hexadienedioic Acid Methyl Ester 3,6-Lactone

Database IDs

• CAS Number: 521-52-8
• PubChem SID: 164235477
• PubChem CID: 54690323

CALCULATED PROPERTIES

• Acid pKa: 6.0776043
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.1256373
• LogD (pH = 7.4): 1.8876123
• Log P: 3.227516
• Molar Refractivity: 88.8913 cm^3
• Polarizability: 33.877647 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow Solid
• Melting Point: 150-151°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V850000

A lichen metabolite with anti-inflammatory properties.

REFERENCES

• Shachak, M., et al.: Science, 236, 1098 (1987)
• Froberg, L., et al.: Lichenologist, 25, 83 (1987)
• Hesbacher, S., et al.: J. Chem. Ecology, 21, 233 (1987)