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(Top) 1 Bioactivity 2 See also 3 References

8-Hydroxyquinoline

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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^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

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.

Tris(8-hydroxyquinolinato)aluminium^[2]

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[edit]

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[edit]

^ Albert, A.; Phillips, J. N. (1956). "264. Ionization Constants of Heterocyclic Substances. Part II. Hydroxy-Derivatives of Nitrogenous Six-Membered Ring-Compounds". Journal of the Chemical Society (Resumed). 1956: 1294–1304. doi:10.1039/JR9560001294.

^ Cölle, M.; Dinnebier, R. E.; Brütting, W. (2002). "The structure of the blue luminescent δ-phase of tris(8-hydroxyquinoline)aluminium(III) (Alq₃)". Chemical Communications. 2002 (23): 2908–9. doi:10.1039/b209164j. PMID 12478807. S2CID 96135270.

^ Katakura, R.; Koide, Y. (2006). "Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq₃)". Inorganic Chemistry. 45 (15): 5730–5732. doi:10.1021/ic060594s. PMID 16841973.

^ Montes, V. A.; Pohl, R.; Shinar, J.; Anzenbacher, P. Jr. (2006). "Effective Manipulation of the Electronic Effects and Its Influence on the Emission of 5-Substituted Tris(8-quinolinolate) Aluminum(III) Complexes". Chemistry: A European Journal. 12 (17): 4523–4535. doi:10.1002/chem.200501403. PMID 16619313.

^ Bardez, E.; Devol, I.; Larrey, B.; Valeur, B. (1997). "Excited-State Processes in 8-Hydroxyquinoline: Photoinduced Tautomerization and Solvation Effects". The Journal of Physical Chemistry B. 101 (39): 7786–7793. doi:10.1021/jp971293u.

^ Phillips, J. P. (1956). "The Reactions of 8-Quinolinol". Chemical Reviews. 56 (2): 271–297. doi:10.1021/cr50008a003.

^ "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.

^ Shen, A. Y.; Wu, S. N.; Chiu, C. T. (1999). "Synthesis and Cytotoxicity Evaluation of some 8-Hydroxyquinoline Derivatives". Journal of Pharmacy and Pharmacology. 51 (5): 543–548. doi:10.1211/0022357991772826. PMID 10411213. S2CID 33085238.

^ Fleischer, H. (2005). "Structural Chemistry of Complexes of (n-1)d¹⁰ns Metal Ions with β-N-Donor Substituted Thiolate Ligands (m=0, 2)". Coordination Chemistry Reviews. 249 (7–8): 799–827. doi:10.1016/j.ccr.2004.08.024.

^ Vivanco, J.M.; Bais, H.P.; Stermitz, F.R.; Thelen, G.C.; Callaway, R.M. (2004). "Biogeographical variation in community response to root allelochemistry: novel weapons and exotic invasion". Ecology Letters. 7 (4): 285–292. Bibcode:2004EcolL...7..285V. doi:10.1111/j.1461-0248.2004.00576.x.

v t e Antiseptics and disinfectants (D08)
Acridine derivatives	Ethacridine lactate 9-Aminoacridine Euflavine
Biguanides and amidines	Dibrompropamidine Chlorhexidine^# Propamidine Hexamidine Polihexanide
Phenol and derivatives	Hexachlorophene Policresulen Phenol Triclosan Triclocarban Chloroxylenol^# Biphenylol Fenticlor
Nitrofuran derivatives	Nitrofurazone
Iodine products	Iodine/octylphenoxypolyglycolether Povidone-iodine^# Diiodohydroxypropane
Quinoline derivatives	Dequalinium Chlorquinaldol Oxyquinoline Clioquinol
Quaternary ammonium compounds	Benzalkonium Benzethonium chloride Cetrimonium (bromide/chloride) Cetylpyridinium Cetrimide Benzoxonium chloride Didecyldimethylammonium chloride
Mercurial products	Mercuric amidochloride Phenylmercuric borate Mercuric chloride Merbromin Nitromersol Thiomersal Mercuric iodide
Silver compounds	Silver nitrate
Alcohols	Propanol (propyl alcohol) Isopropanol (isopropyl alcohol) Ethanol (ethyl alcohol)^#
Other	Potassium permanganate Sodium hypochlorite Halazone Monalazone Hydrogen peroxide Eosin Chloramine-T (tosylchloramide) Octenidine dihydrochloride
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole
Triazoles	Terconazole
Polyenes	Nystatin Natamycin Amphotericin B
Other	Ciclopirox Methylrosaniline