Oxidation of 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone (echinochrome A) by atmospheric oxygen 1. Structure of dehydroechinochrome |
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| Authors: | V L Novikov O P Shestak N P Mishchenko S A Fedoreev E A Vasileva V P Glazunov A A Artyukov |
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| Institution: | 1.G. B. Elyakov Pacific Institute of Bioorganic Chemistry,Far-Eastern Branch of the Russian Academy of Sciences,Vladivostok,Russian Federation |
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| Abstract: | The nondestructive oxidation of 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone by atmospheric oxygen in the ground (triplet 3Σg–) and excited (singlet 1Δg) states in different solvents (acetone, dioxane, ethanol, aqueous ethanol, water) at room temperature involves the initial formation of 7-ethyl-5,6,8-trihydroxy-2,3-dioxo-2,3-dihydro-1,4-naphthoquinone (dehydroechinochrome) accompanied by the release of an H2O2 molecule into the reaction medium. Dehydroechinochrome, being highly susceptible to hydration, successively reacts with two H2O molecules to form 7-ethyl-2,2,3,3,5,6,8-heptahydroxy-2,3-dihydro- 1,4-naphthoquinone as the relatively stable final product. In this form, it can be isolated from the mixture of reaction products. |
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