5,6-Dihydroxyindole

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5,6-Dihydroxyindole
Names
Preferred IUPAC name
1H-Indole-5,6-diol
Other names
  • Dopamine lutine
  • Aminochrome
  • DHI
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number
  • 412-130-9
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
    Key: SGNZYJXNUURYCH-UHFFFAOYSA-N
  • C1=CNC2=CC(=C(C=C21)O)O
Properties
C8H7NO2
Molar mass 149.149 g·mol−1
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
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).

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]

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.

References

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