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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/20 17:24:07」(JST)
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| 8-Hydroxyquinoline[1] |
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IUPAC name
Quinolin-8-ol, 8-Quinolinol
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Other names
1-azanaphthalene-8-ol, Fennosan H 30, hydroxybenzopyridine, hoxybenzopyridine, oxychinolin, oxyquinoline, phenopyridine, quinophenol, oxine
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| Identifiers |
| CAS number |
148-24-3 Y |
| PubChem |
1923 |
| ChemSpider |
1847 Y |
| UNII |
5UTX5635HP Y |
| KEGG |
D05321 Y |
| ChEBI |
CHEBI:48981 Y |
| ChEMBL |
CHEMBL310555 Y |
| ATC code |
G01AC30,A01AB07 D08AH03 R02AA14 |
| Jmol-3D images |
Image 1
Image 2 |
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Oc1cccc2cccnc12
c1cc2cccnc2c(c1)O
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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
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| Properties |
| Molecular formula |
C9H7NO |
| Molar mass |
145.16 g/mol |
| Appearance |
White crystalline needles |
| Density |
1.034 g/cm3 |
| Melting point |
76 °C (169 °F; 349 K) |
| Boiling point |
276 °C (529 °F; 549 K) |
| Hazards |
| MSDS |
External MSDS |
| Main hazards |
flammable |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Y (verify) (what is: Y/N?) |
| Infobox references |
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8-Hydroxyquinoline is an organic compound with the formula C9H7NO. It is a derivative of the heterocycle quinoline by placement of an OH group on carbon number 8. This light yellow compound is widely used commercially, although under a variety of names.[2][3]
Contents
- 1 Synthesis
- 2 As a chelating agent
- 3 Applications
- 4 References
Synthesis
It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol.[4]
As a chelating agent
8-Hydroxyquinoline is a monoprotic bidentate chelating agent. Related ligands are the Schiff bases derived from salicylaldehyde, such as salicylaldoxime, salen and salicylaldehyde isonicotinoylhydrazone (SIH). In neutral solution, the hydroxyl is in the protonated form (pKa=9.89) and the nitrogen is not protonated (pKa=5.13).[5] However, an excited-state zwitterionic isomer exists in which H+ is transferred from the oxygen (giving an oxygen anion) to the nitrogen (giving a protonated nitrogen cation).[6]
Applications
The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties,[7][8] functioning as a transcription inhibitor.[9] Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.[10]
The reaction of 8-hydroxyquinoline with aluminium(III)[11] results in Alq3, a common component of organic light-emitting diodes (OLED's). Variations in the substituents on the quinoline rings affect its luminescence properties.[12]
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.
Hydroxyquinoline was used as a stabilizer of hydrogen peroxide in a rocket fuel oxidizer (T-Stoff) for the German Messerschmitt Me 163 Komet in World War 2.
References
- ^ Nanjing Odyssey Chemicals
- ^ "8-Hydroxyquinoline Safety Data". Oxford University. [dead link]
- ^ "8-Hydroxyquinoline". PAN Pesticides Database.
- ^ Collin, G.; Höke, H. (2005), "Quinoline and Isoquinoline", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_465
- ^ 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.
- ^ 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.
- ^ "8-Hydroxyquinoline". Sigma-Aldrich. Retrieved 2012-05-23.
- ^ 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.
- ^ 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.
- ^ 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.
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Antiseptics and disinfectants (D08)
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| Acridine derivatives |
- Ethacridine lactate
- 9-Aminoacridine
- Euflavine
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| Biguanides and amidines |
- Dibrompropamidine
- Chlorhexidine#
- Propamidine
- Hexamidine
- Polihexanide
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| Phenol and derivatives |
- Hexachlorophene
- Policresulen
- Phenol
- Triclosan
- Chloroxylenol#
- Biphenylol
- Fenticlor
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| Nitrofuran derivatives |
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| Iodine products |
- Iodine/octylphenoxypolyglycolether
- Povidone-iodine#
- Diiodohydroxypropane
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| Quinoline derivatives |
- Dequalinium
- Chlorquinaldol
- Oxyquinoline
- Clioquinol
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| Quaternary ammonium compounds |
- Benzalkonium
- Benzethonium chloride
- Cetrimonium (bromide/chloride)
- Cetylpyridinium
- Cetrimide
- Benzoxonium chloride
- Didecyldimethylammonium chloride
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| Mercurial products |
- Mercuric amidochloride
- Phenylmercuric borate
- Mercuric chloride
- Merbromin
- Thiomersal
- Mercuric iodide
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| Silver compounds |
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| Alcohols |
- Propanol (propyl alcohol)
- Isopropanol (isopropyl alcohol)
- Ethanol (ethyl alcohol)#
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| Other |
- Potassium permanganate
- Sodium hypochlorite
- Hydrogen peroxide
- Eosin
- Tosylchloramide
- Octenidine dihydrochloride
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (i/b/d/q/u/r/p/m/k/v/f)/cong/tumr (n/e/d), sysi/epon
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proc, drug (D2/3/4/5/8/11)
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Gynecological anti-infectives and antiseptics (G01)
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| Antibiotics |
- Candicidin
- Chloramphenicol
- Hachimycin
- Oxytetracycline
- Carfecillin
- Mepartricin
- Clindamycin
- Pentamycin
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| Arsenic compounds |
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| Quinoline derivatives |
- Diiodohydroxyquinoline
- Clioquinol
- Chlorquinaldol
- Dequalinium
- Broxyquinoline
- Oxyquinoline
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| Organic acids |
- Lactic acid
- Acetic acid
- Ascorbic acid
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| Sulfonamides |
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| Antifungals |
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Imidazoles
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- Metronidazole
- Clotrimazole
- Miconazole
- Econazole
- Ornidazole
- Isoconazole
- Tioconazole
- Ketoconazole
- Fenticonazole
- Azanidazole
- Propenidazole
- Butoconazole
- Omoconazole
- Oxiconazole
- Flutrimazole
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Triazoles
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Polyenes
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- Nystatin
- Natamycin
- Amphotericin B
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Other
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- Ciclopirox
- Methylrosaniline
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| Other |
- Clodantoin
- Inosine
- Policresulen
- Nifuratel
- Furazolidone
- Povidone-iodine
- Protiofate
- Lactobacillus fermentum
- Copper usnate
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noco/cong/npls, sysi/epon
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proc/asst, drug (G1/G2B/G3CD)
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Antiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)
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Alveo-
late |
Apicom-
plexa |
Conoidasida/
(Coccidiostats) |
| Cryptosporidiosis |
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| Isosporiasis |
- trimethoprim/sulfamethoxazole#
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| Toxoplasmosis |
- pyrimethamine
- sulfadiazine
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| Aconoidasida |
| Malaria |
Individual
agents |
Hemozoin
inhibitors |
| aminoquinolines |
- (4-): amodiaquine#
- chloroquine#
- (8-): primaquine#
- pamaquine
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| 4-methanolquinolines |
- mefloquine#
- quinine#
- quinidine
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| Other |
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| Antifolates |
DHFR inhibitors
(antifols) |
- proguanil#
- chlorproguanil
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| Sulfonamides |
- sulfadoxine
- sulfamethoxypyrazine
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| Coformulation |
- sulfadoxine/pyrimethamine (SP)#
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Sesquiterpene
lactones |
- artemether#
- artesunate#
- dihydroartemisinin
- artemotil
- artemisinin
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| Other |
- atovaquone (with proguanil as Malarone)
- tetracycline
- doxycycline#
- clindamycin
- pyronaridine
- piperaquine
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Combi-
nations |
| Fixed-dose (coformulated) ACTs |
- artemether/lumefantrine#
- artesunate/amodiaquine (ASAQ)
- artesunate/mefloquine (ASMQ)
- dihydroartemisinin/piperaquine
- artesunate/pyronaridine
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Other combinations
(not co-formulated) |
- artesunate/SP
- artesunate/mefloquine
- quinine/tetracycline
- quinine/doxycycline
- quinine/clindamycin
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| Babesiosis |
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Cilio-
phora |
- Balantidiasis: Tetracycline
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Hetero-
kont |
- Blastocystosis: Metronidazole
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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English Journal
- Determination of As, Cd, Hg and Pb in herbs using slurry sampling electrothermal vaporisation inductively coupled plasma mass spectrometry.
- Lin ML, Jiang SJ.SourceDepartment of Chemistry, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
- Food chemistry.Food Chem.2013 Dec 1;141(3):2158-62. doi: 10.1016/j.foodchem.2013.04.105. Epub 2013 May 10.
- Inductively coupled plasma mass spectrometry coupled with ultrasonic slurry sampling electrothermal vaporisation (USS-ETV-ICP-MS) has been applied to determine As, Cd, Hg and Pb in 0.5% m/v slurries of several herb samples. 1% m/v 8-Hydroxyquinoline was used as the modifier to enhance the ion signal
- PMID 23870942
- Effect of two sonochemical procedures on achieving to different morphologies of lead(II) coordination polymer nano-structures.
- Akhbari K, Morsali A, Retailleau P.SourceDepartment of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14115-4838, Tehran, Islamic Republic of Iran.
- Ultrasonics sonochemistry.Ultrason Sonochem.2013 Nov;20(6):1428-35. doi: 10.1016/j.ultsonch.2013.03.013. Epub 2013 Apr 6.
- Micro and nano-structures of a lead(II) coordination polymer, [Pb2(2-Me-8-Hq)2(MeOH)2]n (1), [2-Me-8-HqH=2-methyl-8-hydroxyquinoline], were synthesized by two sonochemical methods. These new micro and nano-structures were characterized by scanning electron microscopy, X-ray powder diffraction, IR sp
- PMID 23623138
- The eradication of breast cancer cells and stem cells by 8-hydroxyquinoline-loaded hyaluronan modified mesoporous silica nanoparticle-supported lipid bilayers containing docetaxel.
- Wang D, Huang J, Wang X, Yu Y, Zhang H, Chen Y, Liu J, Sun Z, Zou H, Sun D, Zhou G, Zhang G, Lu Y, Zhong Y.SourceDepartment of Pharmaceutical Science, School of Pharmacy, Second Military Medical University, 325 Guohe Road, Shanghai 200433, China.
- Biomaterials.Biomaterials.2013 Oct;34(31):7662-73. doi: 10.1016/j.biomaterials.2013.06.042. Epub 2013 Jul 13.
- Breast cancer stem cells (BCSCs), which can fully recapitulate the tumor origin and are often resistant to chemotherapy and radiotherapy, are currently considered as a major obstacle for breast cancer treatment. To achieve the goal of both targeting BCSCs and bulk breast cancer cells, we developed 8
- PMID 23859657
Japanese Journal
- Realization of white organic light-emitting devices using single green emitter by coupled microcavities with two modes
- Yu Yue,Wu Zhaoxin,Jiao Bo,Ma Lin,Chen Han,Hou Xun
- Appl. Phys. Express 8(2), 022103, 2015-01-22
- … Utilizing tris(8-hydroxyquinoline)aluminum (Alq<inf>3</inf>) as an emitting layer, we obtained a series of WOLEDs whose Commission Internationale de L'Eclairage (CIE) coordinates are on the Planckian curve from [Formula: see text] to [Formula: see text] with current efficiencies in the range of 1.45–2.52 cd A<sup>−1</sup>. …
- NAID 150000110103
- [Paper] Mitigation of Roll-off Property in OLED by Accumulated Electron Reduction at Emission/Electron-Transport Layer Heterojunction Interface
- Minagawa Masahiro,Tsuchida Yusuke,Takahashi Katsuya,Takahashi Akira
- ITE Transactions on Media Technology and Applications 3(2), 127-132, 2015
- … trioxide (MoO3)-doped 9,10-diphenyl-anthracene (DPA, 30 nm)/DPA (10 nm)/5 wt%-5,6,11,12-tetraphenyl-naphthacene (rubrene)-doped DPA (40 nm)/DPA (20 nm)/14 wt%-cesium (Cs)-doped DPA (20 nm)/aluminum (Al, 100 nm, cathode) structure, although a conventional OLED having an ITO (145 nm, anode)/N,N´-Di-[(1-naphthyl)-N,N´-diphenyl]-1,1´-biphenyl)-4,4´- diamine (α-NPD, 20 nm)/5 wt%-rubrene-doped DPA (42 nm)/tris(8-hydroxyquinoline) aluminum (Alq3, 20 nm)/lithium fluoride (LiF, 0.5 nm)/Al (100 nm, cathode) structure exhibited a typical roll-off …
- NAID 130005064338
- A facile approach to improve light extraction for organic light emitting diodes via azobenzene surface relief gratings
- Kim Juhwan,Park Hong-ju,Na Seok-In,Noh Yong-Young,Kim Dong-Yu
- Jpn. J. Appl. Phys. 53(8S3), 08NF02, 2014-07-07
- … The SRGs were applied to OLEDs based on tris(8-hydroxyquinoline)aluminum(III) (Alq<inf>3</inf>) and poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylene vinylene] (MEH-PPV). …
- NAID 150000109651
Related Links
- Synthesis [edit] It is usually prepared from quinoline-8-sulfonic acid and from a Skraup synthesis from 2-aminophenol. [4] As a chelating agent [edit] 8-Hydroxyquinoline is a monoprotic bidentate chelating agent. Related ligands are ...
- Physician reviewed hydroxyquinoline (vaginal) patient information - includes hydroxyquinoline description, dosage and directions. ... What other drugs will affect hydroxyquinoline? It is not likely that other drugs you take orally or inject ...
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