Oxindole

Structural formula
General
Surname	Oxindole
other names	2-indolinone; 2-oxindole; 2,3-dihydro-1 H -indol-2-on; Indolin-2-one;
Molecular formula	C 8 H 7 NO
Brief description	colorless to light red solid
External identifiers / databases
EC number	200-429-5
ECHA InfoCard	100,000,390
PubChem	321710
Wikidata	Q2018788
properties
Molar mass	133.15 g mol −1
Physical state	firmly
Melting point	123-128 ° C
boiling point	227 ° C (at 97 hPa)
solubility	practically insoluble in water; soluble in methanol, ethanol, dimethyl sulfoxide and ether;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	400 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxindole is a chemical compound from the group of indoles and an isomer of indoxyl .

Occurrence

Oxindole is the basic body of the so-called oxindole - alkaloids .

Extraction and presentation

Oxindole is made from aniline and chloroacetyl chloride , among other things . It can also lactamization of o -Aminophenylessigsäure be won.

properties

Oxindole is a colorless to light red solid that is practically insoluble in water.

use

Oxindole is considered an indole analog that shows pharmacological activity. It is also used in hair dyes and as an intermediate for the production of agrochemicals and for chemical syntheses in aldol additions , Claisen condensations or Vilsmeier-Haack reactions in the 3-position or aromatic substitutions in the 5-position. As tyrosine kinase inhibitors, derivatives are possible candidates in cancer therapy .

safety instructions

The occurrence of oxindole in children's urine suggests specific diseases. Tryptophan is metabolized via indole to oxindole, which is broken down in the liver . If oxindole is not broken down there due to a malfunction, it modifies the voltage-dependent sodium channels , reduces motor activity, muscle tone and lowers blood pressure. In hepatic encephalopathy , for example, it is responsible for the occurrence of coma, loss of nerve activity and intellectual abilities.

Individual evidence

↑ ^a ^b ^c ^d ^e entry on oxindole. In: Römpp Online . Georg Thieme Verlag, accessed on June 25, 2016.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet Oxindole, 97% from Sigma-Aldrich , accessed on June 25, 2016 ( PDF ).
↑ ^a ^b Data sheet Oxindole, 97 +% from AlfaAesar, accessed on June 25, 2016 ( PDF )(JavaScript required) .
↑ Helmut Krauch, Werner Kunz: Reactions of organic chemistry . John Wiley & Sons, 2009, ISBN 3-527-62512-7 , pp. 523 ( limited preview in Google Book search).
↑ Oliviero Riggio, Guido Mannaioni, Lorenzo Ridola, Stefania Angeloni, Manuela Merli, Vincenzo Carlà, Filippo Maria Salvatori, Flavio Moroni: Peripheral and Splanchnic Indole and Oxindole Levels in Cirrhotic Patients: A Study on the Pathophysiology of Hepatic Encephalopathy. In: The American Journal of Gastroenterology. 105, 2010, p. 1374, doi : 10.1038 / ajg.2009.738 .

[RömppOnline-1] ↑ ^a ^b ^c ^d ^e entry on oxindole. In: Römpp Online . Georg Thieme Verlag, accessed on June 25, 2016.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ data sheet Oxindole, 97% from Sigma-Aldrich , accessed on June 25, 2016 ( PDF ).

[Alfa-3] Data sheet Oxindole, 97 +% from AlfaAesar, accessed on June 25, 2016 ( PDF )(JavaScript required) .

[Helmut_Krauch,_Werner_Kunz-4] Helmut Krauch, Werner Kunz: Reactions of organic chemistry . John Wiley & Sons, 2009, ISBN 3-527-62512-7 , pp. 523 ( limited preview in Google Book search).

[DOI10.1038/ajg.2009.738-5] Oliviero Riggio, Guido Mannaioni, Lorenzo Ridola, Stefania Angeloni, Manuela Merli, Vincenzo Carlà, Filippo Maria Salvatori, Flavio Moroni: Peripheral and Splanchnic Indole and Oxindole Levels in Cirrhotic Patients: A Study on the Pathophysiology of Hepatic Encephalopathy. In: The American Journal of Gastroenterology. 105, 2010, p. 1374, doi : 10.1038 / ajg.2009.738 .