(2E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one

• ChemBase ID: 177690
• Molecular Formular: C16H14O5
• Molecular Mass: 286.27936
• Monoisotopic Mass: 286.08412355
• SMILES: c1c(ccc(c1OC)C(=O)/C=C/c1cc(c(cc1)O)O)O
• Canonical SMILES: COc1cc(O)ccc1C(=O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H14O5/c1-21-16-9-11(17)4-5-12(16)13(18)6-2-10-3-7-14(19)15(20)8-10/h2-9,17,19-20H,1H3/b6-2+
• InChIKey: JVGNTXGHBHMJDO-QHHAFSJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
• IUPAC Traditional name: sappanchalcone
• Synonyms: (2E)-3-(3,4-Dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one; Sappanchalcone; Sappanchalcone

Database IDs

• CAS Number: 94344-54-4
• PubChem SID: 164233600
• PubChem CID: 5319493

CALCULATED PROPERTIES

• Acid pKa: 7.891572
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.8202102
• LogD (pH = 7.4): 2.6990912
• Log P: 2.821958
• Molar Refractivity: 79.2829 cm^3
• Polarizability: 29.674278 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide
• Apperance: Orange powder; Yellow Solid

DETAILS

Toronto Research Chemicals - S116500

Anti-inflammatory agent.

REFERENCES

• Jeong, G. et al.; Eur. J. Pharmacol. 644, 230 (2010)
• Washiyama, M. et al.; Biol. Pharm. Bull. 32, 941 (2009)