8-Hydroxyquinoline

8-Hydroxyquinoline
Names
	Preferred IUPAC name Quinolin-8-ol
	Other names 1-Azanaphthalene-8-ol, Fennosan H 30, Hydroxybenzopyridine, Oxybenzopyridine, Oxychinolin, Oxyquinoline, Phenopyridine, Quinophenol, Oxine, 8-Quinolinol
Identifiers
CAS Number	148-24-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48981 ;
ChEMBL	ChEMBL310555 ;
ChemSpider	1847 ;
ECHA InfoCard	100.005.193
KEGG	D05321 ;
PubChem CID	1923;
UNII	5UTX5635HP ;
CompTox Dashboard (EPA)	DTXSID5020730 ;
	InChI InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MCJGNVYPOGVAJF-UHFFFAOYSA-N ; InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MCJGNVYPOGVAJF-UHFFFAOYAG;
	SMILES C1=CC2=C(C(=C1)O)N=CC=C2;
Properties
Chemical formula	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
ATC code	G01AC30 (WHO) A01AB07 (WHO) D08AH03 (WHO) R02AA14 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H317, H318, H360D, H410
Precautionary statements	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). Infobox references

8-Hydroxyquinoline (also known as oxine) is an organic compound derived from the heterocycle quinoline. A colorless solid, its conjugate base is a chelating agent, which is used for the quantitative determination of metal ions.

In aqueous solution 8-hydroxyquinoline has a pK_a value of ca. 9.9^[1] It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.

The aluminium complex,^[3] is a common component of 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 antiseptic, disinfectant, and pesticide properties,^[6]^[7] functioning as a 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 Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it.^[11]

References

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

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[11]

Search

8-Hydroxyquinoline

Bioactivity

See also

References

Names



Preferred IUPAC name Quinolin-8-ol
Other names 1-Azanaphthalene-8-ol, Fennosan H 30, Hydroxybenzopyridine, Oxybenzopyridine, Oxychinolin, Oxyquinoline, Phenopyridine, Quinophenol, Oxine, 8-Quinolinol
Identifiers
CAS Number	148-24-3^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48981^Y
ChEMBL	ChEMBL310555^Y
ChemSpider	1847^Y
ECHA InfoCard	100.005.193
KEGG	D05321^Y
PubChem CID	1923
UNII	5UTX5635HP^Y
CompTox Dashboard (EPA)	DTXSID5020730
InChI InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H^Y Key: MCJGNVYPOGVAJF-UHFFFAOYSA-N^Y InChI=1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H Key: MCJGNVYPOGVAJF-UHFFFAOYAG
SMILES C1=CC2=C(C(=C1)O)N=CC=C2
Properties
Chemical formula	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
ATC code	G01AC30 (WHO) A01AB07 (WHO) D08AH03 (WHO) R02AA14 (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H317, H318, H360D, H410
Precautionary statements	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). Infobox references