5,6-Dihydroxyindole
| Names | |
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| IUPAC name
1H-Indole-5,6-diol | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| DrugBank | |
| ECHA InfoCard | 100.101.149 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H7NO2 | |
| Molar mass | 149.149 g·mol−1 |
| Hazards | |
| GHS labelling: | |
| Danger | |
| H302, H318, H411 | |
| P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, P391, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
5,6-Dihydroxyindole is a chemical compound with the molecular formula C8H7NO2. It is an intermediate in the production of the biological pigment eumelanin. 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. 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.