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5,6-Dihydroxyindole

Chemical compound From Wikipedia, the free encyclopedia

5,6-Dihydroxyindole
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5,6-Dihydroxyindole is a chemical compound with the molecular formula C8H7NO2. It is an intermediate in the production of the biological pigment eumelanin.[2] 5,6-Dihydroxyindole is biosynthesized from L-dopachrome in a reaction catalyzed by a tyrosinase enzyme and is further converted into indole-5,6-quinone.[3] In humans, 5,6-dihydroxyindole is involved in the metabolic disorder hawkinsinuria.[3]

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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.[4]

A laboratory synthesis of 5,6-dihydroxyindole can be accomplished starting from 3,4-dibenzyloxybenzaldehyde.[5] 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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