Indole-5,6-quinone

Indole-5,6-quinone is an indolequinone, a chemical compound found in the oxidative browning reaction of fruits like bananas where it is mediated by the tyrosinase type polyphenol oxidase from tyrosine and catecholamines leading to the formation of catechol melanin.[1] Like many quinones it can undergo redox reactions via the corresponding 5,6-dihydroxyindole.[2]

Indole-5,6-quinone

Names
IUPAC name 1H-Indole-5,6-dione
Identifiers
CAS Number	582-59-2
3D model (JSmol)	Interactive image
ChemSpider	389600
PubChem CID	440728
CompTox Dashboard (EPA)	DTXSID90331517
InChI InChI=1S/C8H5NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9H Key: IGGVVGHJSQSLFO-UHFFFAOYSA-N InChI=1/C8H5NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9H Key: IGGVVGHJSQSLFO-UHFFFAOYAN
SMILES C1=CNC2=CC(=O)C(=O)C=C21
Properties
Chemical formula	C8H5NO2
Molar mass	147.13 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• Dopachrome

References

1. Molecular Basis of Catecholamine Biosynthesis in Banana Fruit. Thesis submitted to the R.H. Smith Faculty of Agriculture, Food and Environment Quality Sciences of the Hebrew University of Jerusalem for the degree of Master of Science in Agriculture by Lydia Quansah, March 2009
2. Beer, R. J. S.; Broadhurst, Tom; Robertson, Alexander. "The chemistry of the melanins. Part V. The autoxidation of 5 : 6-dihydroxyindoles". Journal of the Chemical Society (Resumed): 1947. doi:10.1039/JR9540001947.