8-Hydroxyquinoline (also known as oxine) is a
chelating agent which has been used for the
quantitative determination of metal ions.
In aqueous solution 8-hydroxyquinoline has a pK
a value of ca. 9.9 It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-
chelate complexes.
The aluminium complex is a common component of
organic light-emitting diodes (OLEDs). Variations in the substituents on the quinoline rings affect its
luminescence properties.
In the photochemically induced excited-state
zwitterionic isomers are formed in which the hydrogen atom is transferred from oxygen to nitrogen.
The complexes as well as the heterocycle itself exhibit
antiseptic,
disinfectant
A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than st ...
, and pesticide properties, functioning as a
transcription inhibitor. Its solution in alcohol is used in
liquid bandages. It once was of interest as an anti-cancer drug.
A thiol analogue,
8-mercaptoquinoline is also known.
The roots of the invasive plant ''
Centaurea diffusa'' release 8-hydroxyquinoline, which has a negative effect on plants that have not
co-evolved with it.
See also
*
Clioquinol, an antifungal drug and antiprotozoal drug.
*
PBT2
*
QUPIC
PB-22 (QUPIC, SGT-21 or 1-pentyl-1''H''-indole-3-carboxylic acid 8-quinolinyl ester) is a designer drug offered by online vendors as a cannabimimetic agent, and detected being sold in synthetic cannabis products in Japan in 2013. PB-22 represents ...
*
Ionophore
*
Trace metal detection test
References
{{DEFAULTSORT:Hydroxyquinoline, 8-
Antiseptics
Quinolinols