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Indole-5,6-quinone

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Indole-5,6-quinone
Chemical structure of indole-5,6-quinone
Molecular model of indole-5,6-quinone
Names
Preferred IUPAC name 1H-Indole-5,6-dione
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H5NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9HKey: IGGVVGHJSQSLFO-UHFFFAOYSA-N
  • InChI=1/C8H5NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9HKey: 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. Like many quinones it can undergo redox reactions via the corresponding 5,6-dihydroxyindole.

See also

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" (PDF). Archived from the original (PDF) on 2016-03-03. Retrieved 2011-07-05.
  2. Beer, R. J. S.; Broadhurst, Tom; Robertson, Alexander (1954). "The chemistry of the melanins. Part V. The autoxidation of 5 : 6-dihydroxyindoles". Journal of the Chemical Society (Resumed): 1947. doi:10.1039/JR9540001947.


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