Description
4-Hydroxyquinoline is a quinoline alkaloid that has been found in Z. lotus honeys. It is a core component of alkyl-4-hydroxyquinoline quorum sensing molecules such as 2-heptyl-3-hydroxy-4(1H)-quinolone and 2-nonyl-3-hydroxy-4-quinolone. 4-Hydroxyquinoline has been used as a precursor in the synthesis of compounds with antibacterial activity. It has also been used as a fluorescent detection reagent for iron(III) in bovine liver samples.
Chemical Properties
LIGHT BEIGE TO YELLOWISH CRYST. POWDER OR NEEDLES
Uses
4-Hydroxyquinolineis is a raw material in medical research, a hydroxylated quinoline derivative with antimicrobial activity. 4-Hydroxyquinoline showed growth-inhibitory effects against intestinal bacteria. 4-Hydroxyquinoline act as sacrifi
cial scavengers of the photogenerated oxygen species and has been shown to prevent the photodegradation of riboflavin.
Definition
ChEBI: A monohydroxyquinoline carrying a hydroxy group at position 4.
Synthesis Reference(s)
Journal of the American Chemical Society, 68, p. 1264, 1946
DOI: 10.1021/ja01211a038
General Description
4-Quinolinol (4-quinolone) is a quinolone compound which forms the core moiety of antibacterials such as norfloxacin, nalidixic acid, ciprofloxacin and cinoxacin.
Biological Activity
4-hydroxyquinoline is a hydroxylated quinoline derivative with antimicrobial activity. it shows growth-inhibitory effects against intestinal bacteria. it also can be used as sacrificial scavengers of the photogenerated oxygen species.
References
[1] F. KHALLOUKI. HPLC-ESI-MS and GC-EI-MS Identification and Quantitation of Polyphenolics and Alkaloids in Moroccan Jujube Honeys[J]. Journal of Apicultural Science, 2020, 64 1: 287-299. DOI:
10.2478/jas-2020-0029[2] STEPHAN HEEB. Quinolones: from antibiotics to autoinducers[J]. FEMS microbiology reviews, 2011, 35 2: 247-274. DOI:
10.1111/j.1574-6976.2010.00247.x[3] MARIE-GRATIA KAYIRERE . Synthesis and antibacterial activity of new 4-alkoxy, 4-aminoalkyl and 4-alkylthioquinoline derivatives[J]. European Journal of Medicinal Chemistry, 1998, 33 1: Pages 55-63. DOI:
10.1016/s0223-5234(99)80076-2[4] GEORGE C. RAGOS Prodromos B I Mavroudis A Demertzis. A high-sensitive spectrofluorimetric method for the determination of micromolar concentrations of iron(III) in bovine liver with 4-hydroxyquinoline[J]. Farmaco (Societa chimica italiana: 1989), 1998, 53 8: Pages 611-616. DOI:
10.1016/s0014-827x(98)00070-6
