3'-Methoxy-4',5,7-trihydroxyisoflavone

CAS: 36190-95-1

Ref. TR-M269675

Product Information

• Name: 3'-Methoxy-4',5,7-trihydroxyisoflavone
• Synonyms: 5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one, 3'-Methylorobol, 3'-O-Methylorobol, Orobol 3'-Methyl Ether

Description

Applications 3'-Methoxy-4',5,7-trihydroxyisoflavone is a derivative of Genistein (G350000); a compound that exhibits specific inhibitory activity against tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2.
References Akiyama, T., et al.: J. Biol. Chem., 262, 5592 (1987); O'Dell, T.J., et al.: Nature, 353, 588 (1991); Aharonovits, O., et al.: Biochim Biophys. Acta, 1112, 181 (1992); Platanias, L.C., et al.: J. Biol. Chem., 267, 24053 (1992); Yoshida, H., et al.: Biochim. Biophys. Acta, 1137, 321 (1992); Uckun, F.M., et al.: Science, 267, 886 (1995); Merck Index 12th ed. 4395, Huang, R.Q.; Fang, M.J.; Dillon, G.H., Mol. Brain Res. 67: 177-183 (1999)

• Brand: TRC

Chemical properties

• Molecular weight: 300.26
• Formula: C₁₆H₁₂O₆
• Color/Form: Neat
• InChI: InChI=1S/C16H12O6/c1-21-13-4-8(2-3-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3
• InChI key: InChIKey=ZMFBGWWGXBNJAC-UHFFFAOYSA-N
• SMILES: COc1cc(-c2coc3cc(O)cc(O)c3c2=O)ccc1O