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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:
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

Signal Word

Danger

Hazard Statements

H301,H317,H318,H360D,H410

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

Certificates of Analysis (COA)

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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
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
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
Saverio Tardito et al.
Journal of medicinal chemistry, 55(23), 10448-10459 (2012-11-23)
This study reports the structure-activity relationship of a series of 8-hydroxoquinoline derivatives (8-HQs) and focuses on the cytotoxic activity of 5-Cl-7-I-8-HQ (clioquinol, CQ) copper complex (Cu(CQ)). 8-HQs alone cause a dose-dependent loss of viability of the human tumor HeLa and
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