ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Quinoline compounds 4-Quinolinol

4-Quinolinol

Product Name4-Quinolinol
CAS611-36-9
MFC9H7NO
MW145.16
EINECS210-268-2
MOL File611-36-9.mol

Chemical Properties

Melting point	200-202 °C(lit.)
Boiling point	264.27°C (rough estimate)
Density	1.1555 (rough estimate)
refractive index	1.4500 (estimate)
storage temp.	Sealed in dry,Room Temperature
solubility	Soluble in methanol.
form	Crystalline Powder or Needles
pka	2.23, 11.28(at 20℃)
color	Light beige to yellow
Water Solubility	4.8g/L(15 ºC)
BRN	1524969
InChI	1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
InChIKey	PMZDQRJGMBOQBF-UHFFFAOYSA-N
SMILES	Oc1ccnc2ccccc12
LogP	2.450 (est)
CAS DataBase Reference	611-36-9(CAS DataBase Reference)
NIST Chemistry Reference	4-Quinolinol(611-36-9)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36-37/39
WGK Germany	3
RTECS	VC4070000
HS Code	29334900
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
4-Quinolinol	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

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

4-Quinolinol

Chemical Properties

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MSDS

Usage And Synthesis

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