3,4-DIHYDROXY-5-METHOXYBENZOIC ACID

3-O-Methylgallic acid (3,4-Dihydroxy-5-methoxybenzoic acid) is an anthocyanin metabolite and has potent antioxidant capacity. 3-O-methylgallic acid inhibits Caco-2 cell proliferation with an IC50 value of 24.1 μM. 3-O-methylgallic acid also induces cell apoptosis and has anti-cancer effects[1][2][3].

ChEBI: A member of the class of benzoic acids that is gallic acid in which the phenolic hydroxy group at position 3 is converted to the corresponding methyl ether.

[1] Forester SC, et al. Gut metabolites of anthocyanins, gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde, inhibit cell proliferation of Caco-2 cells. J Agric Food Chem. 2010 May 12;58(9):5320-7. DOI:10.1021/jf9040172
[2] Forester SC, The anthocyanin metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals. Mol Carcinog. 2014 Jun;53(6):432-9. DOI:10.1002/mc.21974
[3] Gargouri OD, et al. Synthesis of 3-O-methylgallic acid a powerful antioxidant by electrochemical conversion of syringic acid. Biochim Biophys Acta. 2013 Jun;1830(6):3643-9. DOI:10.1016/j.bbagen.2013.02.012