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5,6-Dihydroxyindole

5,6-Dihydroxyindole, also known as aminochrome, is a chemical compound with the molecular formula C<sub>8</sub>H<sub>7</sub>NO<sub>2</sub>. It is an intermediate in the production of the biological pigment eumelanin. 5,6-Dihydroxyindole is biosynthesized from <small>L</small>-dopachrome in a reaction catalyzed by a tyrosinase enzyme and is further converted into indole-5,6-quinone. In humans, 5,6-dihydroxyindole is involved in the metabolic disorder hawkinsinuria.

In some insects, 5,6-dihydroxyindole is a reactive compound that is produced as a component of defense responses and has antibacterial and antifungal activity.

A laboratory synthesis of 5,6-dihydroxyindole can be accomplished starting from 3,4-dibenzyloxybenzaldehyde. This compound is condensed with nitromethane in a Henry reaction, followed by nitration, reduction of the nitro groups, and hydrogenolysis of the benzyl protecting groups.

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