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Benzoquinones (BQ) have important functions in many biological processes. In alkaline environments, BQs\udcan be hydroxylated at quinoid ring proton positions. Very little is known about the chemical reaction\udleading to these structural transformations as well as about the properties of the obtained hydroxyl\udbenzoquinones. We analyzed the behavior of the naturally occurring 2,6-dimethoxy-1,4-benzoquinone\udunder alkaline conditions and show that upon substitution of methoxy-groups, poly-hydroxyl-derivatives\ud(OHBQ) are formed. The emerging compounds with one or several hydroxyl-substituents on single or fused\udquinone-rings exist in oxidized or reduced states and are very stable under physiological conditions. In\udcomparison with the parent BQs, OHBQs are stronger radical scavengers and redox switchable\udearth-alkaline metal ligands. Considering that hydroxylated quinones appear as biosynthetic intermediates\udor as products of enzymatic reactions, and that BQs present in food or administered as drugs can be\udhydroxylated by enzymatic pathways, highlights their potential importance in biological systems

Hydroxylated derivatives of dimethoxy-1,4-benzoquinone as redox switchable earth-alkaline metal ligands and radical scavengers