A Hydroxyquinone with Amine Oxidase Activity: Preparation and Properties

The preparation and some properties of a hydroxyquinone showing an amine oxidase-like activity are described. The compound, 2-hydroxy-5-methyl-1,4-benzoquinone, oxidizes a wide range of primary amines, both benzylic and non-benzylic, at the expenses of molecular oxygen in the presence of Cu2+ ions, and reacts with hydrazine derivatives leading to stable, inactive adducts. This behaviour is similar to that of 2,4,5-trihydroxyphenylalanine quinone-containing amine oxidases and therefore the present compound could be a useful model to understand the reaction mechanism of those enzymes.