H6878

8-Hydroxyquinoline

Name: 8-Hydroxyquinoline
Brand: SIAL

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

Key Documents

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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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This Item	36524	32502	252565
Sigma-Aldrich H6878 8-Hydroxyquinoline	Supelco 36524 8-Quinolinol	Sigma-Aldrich 32502 8-Quinolinol	Sigma-Aldrich 252565 8-Hydroxyquinoline
mode of action DNA synthesis \| interferes, enzyme \| inhibits	mode of action DNA synthesis \| interferes, enzyme \| inhibits	mode of action DNA synthesis \| interferes, enzyme \| inhibits	mode of action DNA synthesis \| interferes, enzyme \| inhibits
antibiotic activity spectrum fungi	antibiotic activity spectrum fungi	antibiotic activity spectrum fungi	antibiotic activity spectrum fungi
Quality Level 200	Quality Level 100	Quality Level 200	Quality Level 200
form powder	form -	form solid	form -
assay ≥98.5%	assay 98-100% (GC)	assay ≥99% (perchloric acid titration)	assay 98.5%
mp 72.5-74.0 °C	mp 72.5-74.0 °C	mp 72.5-74.0 °C, 72.5-75 °C	mp 72.5-74.0 °C

General description

Chemical structure: quinolone

Application

Used as a lipophilic monoprotic bidentate chelating agent.

Pictograms

GHS06,GHS08,GHS05,GHS09

Signal Word

Danger

Hazard Statements

H301,H317,H318,H360D,H410

Precautionary Statements

P202 - P273 - P280 - P301 + P310 - P302 + P352 - P305 + P351 + P338

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

0000463312

0000463311

0000438824

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Generalized enzymatic mechanism of catalysis by tetrameric L-asparaginases from mesophilic bacteria.

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

Type I Interferon Response Dysregulates Host Iron Homeostasis and Enhances Candida glabrata Infection.

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

Targeting of 111In-labeled dendritic cell human vaccines improved by reducing number of cells.

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

Characterization of 8-hydroxyquinoline derivatives containing aminobenzothiazole as inhibitors of dengue virus type 2 protease in vitro.

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

Copper-dependent cytotoxicity of 8-hydroxyquinoline derivatives correlates with their hydrophobicity and does not require caspase activation.

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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