Abstract:
2,6-Dimethoxyphenol is a phenolic compound that is extensively used for the measurement of
laccase activity, but is often not exploited for its potential as an antioxidant compound. Since
laccase can be used to modify phenolic antioxidants as a way of improving their activities, the
present study investigated the laccase-mediated oxidation of 2,6-dimethoxyphenol in biphasic or
homogenous aqueous-organic media for the production of compounds with higher antioxidant
capacity than the starting substrate. The main product was a dimer (m/z 305.0672), which was
further characterized as a symmetrical C-C linked 3,3’,5,5’-tetramethoxy biphenyl-4,4’-diol. In
the monophasic system, the dimer was preferentially formed when acetone was used as co34
solvent, while in the biphasic system, formation of the dimer increased as the concentration of
ethyl acetate was increased from 50 to 90 %. The dimer showed higher antioxidant capacity than
the substrate (≈ 2×) as demonstrated by standard antioxidant assays (DPPH and FRAP). These
results demonstrate that a product of the laccase-catalysed oxidation of 2,6-dimethoxyphenol can
find useful application as a bioactive compound.
