8-hidroxichinolină

8-hidroxichinolină
Identificare
SMILES
Număr CAS148-24-3
ChEMBLCHEMBL310555
PubChem CID1923
Formulă chimicăC₉H₇NO[1]  Modificați la Wikidata
Masă molară145,053 u.a.m.[2]  Modificați la Wikidata
Punct de topire74 °C[3]  Modificați la Wikidata
Sunt folosite unitățile SI și condițiile de temperatură și presiune normale dacă nu s-a specificat altfel.
Modifică date / text Consultați documentația formatului

8-hidroxichinolina este un compus organic cu formula C9H7NO. Este un derivat de chinolină, prin hidroxilare în poziția 8 a nucleului aromatic. Este un compus solid de culoare galbenă.[4]

Obținere

8-hidroxichinolina se obține în urma sintezei Skraup, plecând de la 2-aminofenol.[5]

Proprietăți

Tris(8-hidroxichinolinat) de aluminiu, un complex format de 8-hidroxichinolină.[6]

8-hidroxichinolina prezintă o moleculă planară. pKa-ul său are valoarea de 9,89, caracteristic pentru un fenol.[7] În starea de zwitterion indusă fotochimic, ionul H+ este transferat de la atomul de oxigen la cel de azot.[8]

Este un agent chelatant bidentat monoprotic, formând complecși cu diverși ioni.

Utilizări

Atât complecșii de coordinare, cât și compusul în sine, prezintă o activitate chimioterapică, antiseptică și dezinfectantă,[9][10] funcționând ca inhibitori de transcripție.[11] Este compusul de bază de la care s-a conceput o nouă clasă de chimioterapice, derivații halogenați de 8-hidroxichinolină. Câteva exemple sunt:

Note

  1. ^ a b „8-hidroxichinolină”, 8-HYDROXYQUINOLINE (în engleză), PubChem, accesat în  
  2. ^ „8-hidroxichinolină”, 8-HYDROXYQUINOLINE (în engleză), PubChem, accesat în  
  3. ^ Jean-Claude Bradley Open Melting Point Dataset 
  4. ^ „8-Hydroxyquinoline Safety Data”. Oxford University. Arhivat din original la . Accesat în . 
  5. ^ Collin, G.; Höke, H. (), „Quinoline and Isoquinoline”, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a22_465 
  6. ^ 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 (23): 2908–9. doi:10.1039/b209164j. PMID 12478807. 
  7. ^ 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: 1294–1304. doi:10.1039/JR9560001294. 
  8. ^ 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. 101 (39): 7786–7793. doi:10.1021/jp971293u. 
  9. ^ Phillips, J. P. (). „The Reactions of 8-Quinolinol”. Chemical Reviews. 56 (2): 271–297. doi:10.1021/cr50008a003. 
  10. ^ „8-Hydroxyquinoline”. Medical Dictionary Online. Arhivat din original la . Accesat în . 
  11. ^ „8-Hydroxyquinoline”. Sigma-Aldrich. Accesat în . 


v • d • m
Preparate dermatologice: antiseptice și dezinfectante (cod ATC D08)
Acridine
Alcooli
Biguanide și amidine
Compuși de amoniu cuaternar
Chinoline
Derivați de iod
Derivați de mercur
Fenoli
Altele

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