(5E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione

• ChemBase ID: 170766
• Molecular Formular: C13H14O4
• Molecular Mass: 234.24786
• Monoisotopic Mass: 234.08920893
• SMILES: c1(c(ccc(c1)/C=C/C(=O)CC(=O)C)O)OC
• Canonical SMILES: COc1cc(/C=C/C(=O)CC(=O)C)ccc1O
• InChI: InChI=1S/C13H14O4/c1-9(14)7-11(15)5-3-10-4-6-12(16)13(8-10)17-2/h3-6,8,16H,7H2,1-2H3/b5-3+
• InChIKey: SQDOMQCCCHMXBP-HWKANZROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione
• IUPAC Traditional name: (5E)-6-(4-hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione
• Synonyms: (E)-6-(4-Hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione; (5E)-6-(4-Hydroxy-3-methoxyphenyl)-5-hexene-2,4-dione

Database IDs

• CAS Number: 189181-53-1
• PubChem SID: 164226676
• PubChem CID: 10489861

CALCULATED PROPERTIES

• Acid pKa: 8.906739
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.2261593
• LogD (pH = 7.4): 2.212978
• Log P: 2.226329
• Molar Refractivity: 64.9503 cm^3
• Polarizability: 24.486275 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Dimethyl Formamide; Ethyl Acetate; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - H946385

Curcumin (C838500) and gingerdione derivative. A possible human glyoxalase I inhibitor. Flavor modifier.

REFERENCES

• Yuan, M. et al.; Bioorg. Med. Chem. 19, 1189 (2011)
• Ley, J. et al.; J. Agr. Food Chem. 56, 6656 (2008)