8-Hydroxyquinoline
Names | |
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Preferred IUPAC name
Quinolin-8-ol | |
Other names
1-Azanaphthalene-8-ol, Fennosan H 30, Hydroxybenzopyridine, Oxybenzopyridine, Oxychinolin, Oxyquinoline, Phenopyridine, Quinophenol, Oxine, 8-Quinolinol
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.005.193 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H7NO | |
Molar mass | 145.16 g/mol |
Appearance | White crystalline powder |
Density | 1.034 g/cm3 |
Melting point | 76 °C (169 °F; 349 K) |
Boiling point | 276 °C (529 °F; 549 K) |
Pharmacology | |
G01AC30 (WHO) A01AB07 (WHO) D08AH03 (WHO) R02AA14 (WHO) | |
Hazards | |
GHS labelling: | |
Danger | |
H301, H317, H318, H360D, H410 | |
P202, P273, P280, P301+P310, P302+P352, P305+P351+P338 | |
Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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8-Hydroxyquinoline (also known as oxine) is an
chelating agent, which is used for the quantitative determination
of metal ions.
In aqueous solution 8-hydroxyquinoline has a pKa value of ca. 9.9chelate complexes.
The aluminium complex,organic light-emitting diodes (OLEDs). Substituents on the quinoline ring affect the luminescence properties.[4]
In its photo-induced excited-state, 8-hydroxyquinoline converts to zwitterionic isomers, in which the hydrogen atom is transferred from oxygen to nitrogen.[5]
Bioactivity
The complexes as well as the heterocycle itself exhibit
transcription inhibitor.[8] Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.[9]
A thiol analogue, 8-mercaptoquinoline is also known.[10]
The roots of the invasive plant co-evolved with it.[11]
See also
- Nitroxoline (5-nitro-8-hydroxyquinoline), an antiprotozoal drug
- PBT2
- QUPIC
- Ionophore
- Trace metal detection test
References
- .
- S2CID 96135270.
- PMID 16841973.
- PMID 16619313.
- .
- .
- ^ "8-Hydroxyquinoline". Medical Dictionary Online. Archived from the original on 2016-10-09. Retrieved 2016-03-09.
- ^ "8-Hydroxyquinoline". Sigma-Aldrich. Retrieved 2022-02-15.
- S2CID 33085238.
- .
- .