Oxindole

Oxindole

Names
Preferred IUPAC name Oxindole
Systematic IUPAC name 2,3-Dihydro-1H-indol-2-one
Identifiers
CAS Number	59-48-3
3DMet	B04450
Beilstein Reference	114692
ChEBI	CHEBI:31697
ChEMBL	ChEMBL40823
ChemSpider	284794
EC Number	200-429-5
Gmelin Reference	637057
Jmol interactive 3D	Image
KEGG	C12312
MeSH	Oxindole
PubChem	321710
RTECS number	NM2080500
UNII	0S9338U62H
InChI InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10) Key: JYGFTBXVXVMTGB-UHFFFAOYSA-N
SMILES c1ccc2c(c1)CC(=O)N2
Properties
Chemical formula	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).
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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

• Indoline
• Indole
• Indene
• Benzofuran
• Isoindoline
• Carboline
• Isatin
• Methylindole
• Carbazole
• Pyrrole
• Skatole
• Benzene

References

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.