8-Hydroxyquinoline (also known as oxine) is a
chelating agent
Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...
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
Luminescence is spontaneous emission of light by a substance not resulting from heat; or "cold light".
It is thus a form of cold-body radiation. It can be caused by chemical reactions, electrical energy, subatomic motions or stress on a cryst ...
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
Transcription is the process of copying a segment of DNA into RNA. The segments of DNA transcribed into RNA molecules that can encode proteins are said to produce messenger RNA (mRNA). Other segments of DNA are copied into RNA molecules called ...
. 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
''Centaurea diffusa'', also known as diffuse knapweed, white knapweed or tumble knapweed, is a member of the genus ''Centaurea'' in the family Asteraceae. This species is common throughout western North America but is not actually native to the ...
'' 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
PBT2 is a safe-for-human-use Zinc ionophore and an experimental drug candidate. It is a second-generation 8-hydroxyquinoline analog intended to be a successor to clioquinol and a potential treatment of Alzheimer's disease and Huntington's disease ...
*
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 The trace metal detection test or technique was developed during the Vietnam War in the 1960s to identify people who may have been carrying firearms against their skin. A 0.2% solution of 8-hydroxyquinoline in isopropanol sprayed on the skin and ill ...
References
{{DEFAULTSORT:Hydroxyquinoline, 8-
Antiseptics
Quinolinols