Structure via PubChem · Public domain (PubChem)
oxindole
Sign in to saveAlso known as 2-oxindole, 1,3-dihydroindol-2-one, 2-indolinone, 1,3-dihydro-(2H)-indol-2-One, Indolin-2-one, 3H-indol-2-ol
Oxindole (2-indolone) is an aromatic heterocyclic organic compound with the formula . 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. Classified as a cyclic amide, it is a pale yellow solid.
Chemical data
- Formula
- C8H7NO
- Molecular weight
- 133.15 g/mol
- IUPAC name
- 1,3-dihydroindol-2-one
- SMILES
- C1C2=CC=CC=C2NC1=O
- InChIKey
- JYGFTBXVXVMTGB-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 133.053
Show 5 more facts
- chemical formula
- C₈H₇NO
- canonical SMILES
- C1C2=CC=CC=C2NC1=O
- melting point
- 126.0
- found in taxon
- Penicillium
- Commons category
- Oxindole
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Formation and reactions
- Oxindoles
- References
Oxindole (2-indolone) is an aromatic heterocyclic organic compound with the formula . 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. Classified as a cyclic amide, it is a pale yellow solid.
==Formation and reactions== Oxindole is derived in nature from tryptophan, 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.
Excerpted from Wikipedia’s “oxindole” article, available under the CC BY-SA 4.0 licence.