Oxindole

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Oxindole
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Oxindole
Systematic IUPAC name
2,3-Dihydro-1H-indol-2-one
Identifiers
59-48-3 YesY
3D model (Jmol) Interactive image
3DMet B04450
114692
ChEBI CHEBI:31697 YesY
ChEMBL ChEMBL40823 YesY
ChemSpider 284794 YesY
ECHA InfoCard 100.000.390
EC Number 200-429-5
637057
KEGG C12312 N
MeSH Oxindole
PubChem 321710
RTECS number NM2080500
UNII 0S9338U62H N
Properties
C8H7NO
Molar mass 133.15 g·mol−1
Melting point 128 °C (262 °F; 401 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Oxindole (2-indolone) is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Oxindole is a modified indoline with a substituted carbonyl at the second position of the 5-member indoline ring.

Oxindole is a tryptophan derivative and in human biology is formed by gut bacteria ("normal flora"). It is normally metabolized and detoxified from the body by the liver. In excess, it can cause sedation, muscle weakness, hypotension, and coma. Patients with hepatic encephalopathy have been recorded to have elevated serum oxindole levels.[1]

Related aromatic compounds[edit]

References[edit]

  1. ^ Riggio, Oliviero; Mannaioni, Guido; Ridola, Lorenzo; Angeloni, Stefania; Merli, Manuela; Carlà, Vincenzo; Salvatori, Filippo Maria; Moroni, Flavio (2 February 2010). "Peripheral and Splanchnic Indole and Oxindole Levels in Cirrhotic Patients: A Study on the Pathophysiology of Hepatic Encephalopathy". The American Journal of Gastroenterology. 105 (6): 1374–1381. doi:10.1038/ajg.2009.738.