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H6878

Sigma-Aldrich

8-Hydroxyquinoline

Synonym(s):

8-Quinolinol, 8-Hydroxyquinoline, 8-Oxychinolin, Oxine

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
Molecular Weight:
145.16
Beilstein:
114512
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.21

Assay

≥98.5%

Quality Level

form

powder

mp

72.5-74.0 °C

antibiotic activity spectrum

fungi

Mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

Oc1cccc2cccnc12

InChI

1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

InChI key

MCJGNVYPOGVAJF-UHFFFAOYSA-N

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General description

Chemical structure: quinolone

Application

Used as a lipophilic monoprotic bidentate chelating agent.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Repr. 1B - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Pawel Strzelczyk et al.
Scientific reports, 10(1), 17516-17516 (2020-10-17)
The mechanism of catalysis by the L-glutaminase-asparaginase from Pseudomonas 7A (PGA) was investigated using structural, mass spectrometry, and kinetic data. We had previously proposed mechanism of hydrolysis of L-Asn by the type II L-asparaginase from E. coli (EcAII), but that
María Isabel Fernández-Bachiller et al.
Journal of medicinal chemistry, 53(13), 4927-4937 (2010-06-16)
Tacrine and PBT2 (an 8-hydroxyquinoline derivative) are well-known drugs that inhibit cholinesterases and decrease beta-amyloid (Abeta) levels by complexation of redox-active metals, respectively. In this work, novel tacrine-8-hydroxyquinoline hybrids have been designed, synthesized, and evaluated as potential multifunctional drugs for
Michael Riedelberger et al.
Cell host & microbe, 27(3), 454-466 (2020-02-23)
Type I interferons (IFNs-I) fulfil multiple protective functions during pathogenic infections, but they can also cause detrimental effects and enhance immunopathology. Here, we report that IFNs-I promote the dysregulation of iron homeostasis in macrophages during systemic infections with the intracellular
David M Rubush et al.
Journal of the American Chemical Society, 134(33), 13554-13557 (2012-08-09)
The desymmetrization of p-peroxyquinols using a Brønsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy
Steve Comby et al.
Inorganic chemistry, 51(19), 10158-10168 (2012-09-15)
A novel near-infrared (NIR) emissive lanthanide-based zinc sensor was designed, based on the self-assembly in aqueous solution between the nonemissive coordinatively unsaturated Yb(III) cyclen complex 2·Yb and the sulfonated 8-hydroxyquinoline (8-HQS) chromophore, which was employed as a sensitizing antenna. The

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