维基百科

用户:DoroWolf/沙盒

< User:DoroWolf
DoroWolf/沙盒
Skeletal formula of 8-hydroxyquinoline
Ball-and-stick model of the 8-hydroxyquinoline molecule
8-hydroxyquinoline
IUPAC名
Quinolin-8-ol
别名 1-Azanaphthalene-8-ol, Fennosan H 30, Hydroxybenzopyridine, Oxybenzopyridine, Oxychinolin, Oxyquinoline, Phenopyridine, Quinophenol, Oxine, 8-Quinolinol
识别
CAS号 148-24-3  checkY
PubChem 1923
ChemSpider 1847
SMILES
 
  • C1=CC2=C(C(=C1)O)N=CC=C2
InChI
 
  • 1/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H
InChIKey MCJGNVYPOGVAJF-UHFFFAOYAG
ChEBI 48981
KEGG D05321
性质
化学式 C9H7NO
摩尔质量 145.16 g/mol g·mol⁻¹
外观 White crystalline needles
密度 1.034 g/cm3
熔点 76 °C（349 K）
沸点 276 °C（549 K）
药理学
ATC代码 G01AC30（G01），A01AB07 D08AH03 R02AA14
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》（简称“GHS”）中有毒物质的标签图案《全球化学品统一分类和标签制度》（简称“GHS”）中对人体有害物质的标签图案《全球化学品统一分类和标签制度》（简称“GHS”）中腐蚀性物质的标签图案《全球化学品统一分类和标签制度》（简称“GHS”）中对环境有害物质的标签图案
GHS提示词 Danger
H-术语 <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="危险说明述有误">HH301, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="危险说明述有误">HH317, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="危险说明述有误">HH318, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="危险说明述有误">HH360D, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="危险说明述有误">HH410
P-术语 <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="防范说明有误">PP202, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="防范说明有误">PP273, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="防范说明有误">PP280, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="防范说明有误">PP301 + P310, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="防范说明有误">PP302 + P352, <span class="abbr skin-invert" style="color: blue; border-bottom: 1px dotted blue" title="防范说明有误">PP305 + P351 + P338
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

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 pKa 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

编辑

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]

See also

编辑

References

编辑
  1. ^ Albert, A.; Phillips, J. N. 264. Ionization Constants of Heterocyclic Substances. Part II. Hydroxy-Derivatives of Nitrogenous Six-Membered Ring-Compounds. Journal of the Chemical Society (Resumed). 1956, 1956: 1294–1304. doi:10.1039/JR9560001294. 
  2. ^ Cölle, M.; Dinnebier, R. E.; Brütting, W. The structure of the blue luminescent δ-phase of tris(8-hydroxyquinoline)aluminium(III) (Alq3). Chemical Communications. 2002, 2002 (23): 2908–9. PMID 12478807. S2CID 96135270. doi:10.1039/b209164j. 
  3. ^ Katakura, R.; Koide, Y. Configuration-Specific Synthesis of the Facial and Meridional Isomers of Tris(8-hydroxyquinolinate)aluminum (Alq3). Inorganic Chemistry. 2006, 45 (15): 5730–5732. PMID 16841973. doi:10.1021/ic060594s. 
  4. ^ Montes, V. A.; Pohl, R.; Shinar, J.; Anzenbacher, P. Jr. 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. 2006, 12 (17): 4523–4535. PMID 16619313. doi:10.1002/chem.200501403. 
  5. ^ Bardez, E.; Devol, I.; Larrey, B.; Valeur, B. Excited-State Processes in 8-Hydroxyquinoline: Photoinduced Tautomerization and Solvation Effects. The Journal of Physical Chemistry B. 1997, 101 (39): 7786–7793. doi:10.1021/jp971293u. 
  6. ^ Phillips, J. P. The Reactions of 8-Quinolinol. Chemical Reviews. 1956, 56 (2): 271–297. doi:10.1021/cr50008a003. 
  7. ^ 8-Hydroxyquinoline. Medical Dictionary Online. [2016-03-09]. （原始内容存档于2016-10-09）. 
  8. ^ 8-Hydroxyquinoline. Sigma-Aldrich. [2022-02-15]. 
  9. ^ Shen, A. Y.; Wu, S. N.; Chiu, C. T. Synthesis and Cytotoxicity Evaluation of some 8-Hydroxyquinoline Derivatives. Journal of Pharmacy and Pharmacology. 1999, 51 (5): 543–548. PMID 10411213. S2CID 33085238. doi:10.1211/0022357991772826  . 
  10. ^ Fleischer, H. Structural Chemistry of Complexes of (n-1)d10ns Metal Ions with β-N-Donor Substituted Thiolate Ligands (m=0, 2). Coordination Chemistry Reviews. 2005, 249 (7–8): 799–827. doi:10.1016/j.ccr.2004.08.024. 
  11. ^ Vivanco, J.M.; Bais, H.P.; Stermitz, F.R.; Thelen, G.C.; Callaway, R.M. Biogeographical variation in community response to root allelochemistry: novel weapons and exotic invasion. Ecology Letters. 2004, 7 (4): 285–292. doi:10.1111/j.1461-0248.2004.00576.x. 

Template:Antiprotozoal agent

检索自“https://zh.wikipedia.org/w/index.php?title=User:DoroWolf/沙盒&oldid=79580057”