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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

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Certificates of Analysis (COA)

Lot/Batch Number
SZB90900V
SZB90560
SZB90560V
SZB90900
SZBA1250V

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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
Erik H J G Aarntzen et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 19(6), 1525-1533 (2013-02-06)
Anticancer dendritic cell (DC) vaccines require the DCs to relocate to lymph nodes (LN) to trigger immune responses. However, these migration rates are typically very poor. Improving the targeting of ex vivo generated DCs to LNs might increase vaccine efficacy
Huiguo Lai et al.
Antiviral research, 97(1), 74-80 (2012-11-07)
Four serotypes of dengue virus (DENV1-4), mosquito-borne members of Flaviviridae family cause frequent epidemics causing considerable morbidity and mortality in humans throughout tropical regions of the world. There is no vaccine or antiviral therapeutics available for human use. In a
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
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