SKU: H006  / 
    CAS Number: 148-24-3

    8-Hydroxyquinoline

    $40.94 - $254.40

    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.  When in alcohol, the solution can be used in liquid bandages.  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.

    Application Used as a chelating agent and quantitative determination of metal ions. Can be used as a carrier for radio-indium for diagnostic purposes.
    Mechanism of Action 8-Hydroxyquinoline is a RNA synthesis inhibitor that interferes with transcription. The antifungal activity appears to be structurally related but is not yet characterized.
    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).

    Solubility Freely soluble in ethanol, acetone, chloroform, and benzene. Insoluble in water.
    References

    Elgimabi MN and Ahmed OK (2009) Effects of bactericides and sucrose-pulsing on vase life of rose cut flowers (Rosa hybirida). Bot. Res. Intl. 2 (3):164-168

    Fraser RS and Creanor J (2012)  The mechanism of inhibition of ribonucleic acid synthesis by 8-hydroxyquinoline and the antibiotic Lomofungin. Biochem. J.  147(3):401-410

    Geels FP, Schmidt DL and Schippers B (1985)  The use of 8-hydroxyquinoline for the isolation and prequalification of plant growth-stimulating rhizosphere pseudomonads. B. Biol Fert Soils 1(4):167-173 

    Hojjati Y, Khalighi A and Farokhzad AR (2007)  Chemical treatments of Eustoma cut flower cultivars for enhanced vase life. J. Agric. and Soc. Sci. 1813–2235

    Liang SH et al (2015)  Novel fluorinated 8-Hydroxyquinoline based metal ionophores for exploring the metal hypothesis of Alzheimer’s Disease. ACS Med. Chem. Lett. 6(9):1025-1029

    Vivanco JM et al (2004)  Biogeographical variation in community response to root allelochemistry: Novel weapons and exotic invasion. Ecol. Lett. 7(4):285-292