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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:
148-24-3
Molecular Weight:
145.16
Beilstein:
114512
EC Number:
205-711-1
MDL number:
MFCD00006807
UNSPSC Code:
12352005
PubChem Substance ID:
24895771
NACRES:
NA.21

Assay

≥98.5%

Quality Level

200

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

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
0000362693
0000362694
0000362695
0000322543
0000322542

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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
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
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
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
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