3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

• ChemBase ID: 174321
• Molecular Formular: C16H12O7
• Molecular Mass: 316.26228
• Monoisotopic Mass: 316.05830272
• SMILES: c1(cc(c2c(c1)oc(c(c2=O)O)c1cc(c(cc1)OC)O)O)O
• Canonical SMILES: COc1ccc(cc1O)c1oc2cc(O)cc(c2c(=O)c1O)O
• InChI: InChI=1S/C16H12O7/c1-22-11-3-2-7(4-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
• InChIKey: FPLMIPQZHHQWHN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5,7-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: tamarixetin
• Synonyms: 3,5,7-Trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one; 3,3',5,7-Tetrahydroxy-4'-methoxyflavone; Tamaraxetin; 4'-Methoxyquercetin; 4'-Methylquercetin; Quercetin 4'-methyl ether; Tamarixetin; 4'-O-Methyl Quercetin; Tamarixetin

Database IDs

• CAS Number: 603-61-2
• PubChem SID: 164230231
• PubChem CID: 5281699

CALCULATED PROPERTIES

• Acid pKa: 6.3820324
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 2.2488894
• LogD (pH = 7.4): 1.1725374
• Log P: 2.3021934
• Molar Refractivity: 81.3445 cm^3
• Polarizability: 30.311312 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder

DETAILS

Toronto Research Chemicals - M326580

A major metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.

REFERENCES

• Duenas, M. et al.: Eur. Food Res. Technol., 232, 103 (2011)
• Ameho, C.K. et al.: J. Nutrit. Biochem., 19, 467 (2011)
• Angeloni, C. et al.: Biochimie, 89, 73 (2011)