(1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

• ChemBase ID: 165744
• Molecular Formular: C20H18O6
• Molecular Mass: 354.35332
• Monoisotopic Mass: 354.1103383
• SMILES: c1(c(ccc(c1)/C=C/C(=O)CC(=O)/C=C/c1ccc(c(c1)O)O)O)OC
• Canonical SMILES: COc1cc(/C=C/C(=O)CC(=O)/C=C/c2ccc(c(c2)O)O)ccc1O
• InChI: InChI=1S/C20H18O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)12-15(21)6-2-13-4-8-17(23)19(25)10-13/h2-11,23-25H,12H2,1H3/b6-2+,7-3+
• InChIKey: FFRFJIZJLZXEJX-YPCIICBESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• IUPAC Traditional name: (1E,6E)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
• Synonyms: (1E,6E)-1-(3,4-Dihydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione; Demethyl Curcumin

Database IDs

• CAS Number: 149732-51-4
• PubChem SID: 162259877
• PubChem CID: 5469426

CALCULATED PROPERTIES

• Acid pKa: 8.810825
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.9784193
• LogD (pH = 7.4): 3.962026
• Log P: 3.9786305
• Molar Refractivity: 99.3283 cm^3
• Polarizability: 36.96462 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Dark Orange Solid
• Melting Point: 183-187°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D230865

A metabolite of Curcumin (C838500) with potent activity against Trypanosoma and Leishmania species.

REFERENCES

• Asai, A., et al.: Life Sci., 67, 2785 (2000)
• Sharma, R., et al.: Eur. J. Cancer, 41, 1955 (2000)
• King, R., et al.: Curr. Drug Metab., 7, 541 (2000)