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22019

Sigma-Aldrich

8-Quinolinol

≥99% (perchloric acid titration)

Synonym(s):

8-Hydroxyquinoline, 8-Oxychinolin, Oxine

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
148-24-3
Molecular Weight:
145.16
Beilstein/REAXYS Number:
114512
EC Number:
205-711-1
MDL number:
MFCD00006807
UNSPSC Code:
12352100
PubChem Substance ID:
57647959

Quality Level

100

assay

≥99% (perchloric acid titration)

form

solid

ign. residue

≤0.05% (as SO4)

mp

70-76 °C
72.5-74.0 °C

anion traces

chloride (Cl-): ≤20 mg/kg
sulfate (SO42-): ≤100 mg/kg

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SZB90900V
SZB90560
SZB90560V
SZB90900
SZBA1250V

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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
Mahmud Tareq Hassan Khan et al.
Journal of medicinal chemistry, 52(1), 48-61 (2008-12-17)
In the present work, 22 compounds of the U.S. NCI compound library (size 273K) were identified as putative thermolysin binders by structure based virtual screening with the ICM software (ICM-VLS). In vitro competitive binding assays confirmed that 12 were thermolysin
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
Bhimashankar Mitkari et al.
Experimental neurology, 239, 158-162 (2012-10-13)
Cell therapies from various sources have been under intense research in stroke. Efficient homing of the cells to the injured brain without complications is necessary to realize the therapeutic potential of cell therapy. Intra-arterial (IA) infusion of cells bypasses the
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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