8-Hydroxyquinoline

- Overview
  - 8-Hydroxyquinoline is a quinolone compound and antifungal with chelating properties. It is a natural product found in the root exudate of the invasive plant Centaurea diffusa. When in aqueous solution, it reacts with metal ions, forming 8-hydroxyquinoline-chelate complexes. The complexes and the heterocycle itself have disinfectant properties. Its halogenated derivatives can be used as anti-infectives.
    8-Hydroxyquinoline is freely soluble in ethanol, acetone, chloroform, and benzene but is insoluble in water.
    
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    Background
    
    8-Hydroxyquinoline is a RNA synthesis inhibitor that interferes with transcription. The antifungal activity appears to be structurally related but is not yet characterized.
- Properties
  - CAS Number
    
    148-24-3
    
    Molecular Formula
    
    C9H7NO
    
    Molecular Weight
    
    145.16
    
    Appearance
    
    White or light yellow crystalline powder
    
    Solubility
    
    Freely soluble in ethanol, acetone, chloroform, and benzene. Insoluble in water.
    
    Other Properties
    
    Source: Synthetic
    Water Content (Karl Fischer): ≤0.5%
    Assay: ≥99.0%
    Residue On Ignition: ≤0.5%
    Heavy Metals: Pb ≤ 0.001%
    Purity Level: ≥99.0%
    
    Storage
    
    2-8 °C
    
    * For research use only
- Applications
  - Application Description
    
    Spectrum: Effective against fungi including Trichophyton mentagrophytes, Myrothecium verrucaria, and Trichoderma viride
    
    Microbiology Applications: 8-Hydroxyquinoline can inhibit RNA synthesis in yeast cells by chelating essential divalent ions Mn2+ and Mg2+ required for RNA polymerase activity.
    
    Plant Biology Applications: 8-Hydroxyquinoline is a floral preservative for cut flowers, increasing vase life by ~ 40% (Elgimabi and Ahmed, 2009) (Hojjati, 2007).
    8-Hydroxyquinoline is a chelator of available iron and this property can be exploited by using the compound as a selective agent in low-iron media to screen for plant growth-stimulating and antagonistic fluorescent pseudomonads (Geels et al, 1985).
    
    Eukaryotic Cell Culture Applications: 8-Hydroxyquinoline can be fluorinated to increase its activity as a metal ionophore and therefore is a promising diagnostic tool as a metal-binding agent capable of dissolving amyloid-beta (Aβ) deposits of zinc, copper and iron involved in the metal hypothesis of Alzheimer’s disease (Liang SH et al, 2015).