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Sigma-Aldrich

5-Chloro-7-iodo-8-quinolinol

≥95.0% (HPLC)

Synonym(s):

5-Chloro-8-hydroxy-7-iodoquinoline, Clioquinol, Iodochlorhydroxyquin

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About This Item

Empirical Formula (Hill Notation):
C9H5ClINO
CAS Number:
130-26-7
Molecular Weight:
305.50
Beilstein:
153637
EC Number:
204-984-4
MDL number:
MFCD00006787
UNSPSC Code:
12352100
PubChem Substance ID:
57648095
NACRES:
NA.22

Quality Level

200

Assay

≥95.0% (HPLC)

form

powder

solubility

dioxane: soluble 0.5 g/10 mL, clear, faintly yellow to yellow

SMILES string

Oc1c(I)cc(Cl)c2cccnc12

InChI

1S/C9H5ClINO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

InChI key

QCDFBFJGMNKBDO-UHFFFAOYSA-N

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General description

5-Chloro-7-iodo-8-quinolinol is an antibiotic with metal-binding properties and exhibits anticancer activity in vitro and in vivo. 5-Chloro-7-iodo-8-quinolinol, its glucuronide and sulfate in serum, urine and milk has been quantitated by gas chromatography.

Application

5-Chloro-7-iodo-8-quinolinol has been used in analysis of intracellular free zinc ions with the FluoZin-3 probes using fluorescence microscopy.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H317,H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A gas chromatographic determination method of 5-chloro-7-iodo-8-quinolinol and its conjugates in biological fluids.
C Chen et al.
Chemical & pharmaceutical bulletin, 24(1), 97-101 (1976-01-01)
Alessio Innocenti et al.
Bioorganic & medicinal chemistry letters, 18(5), 1583-1587 (2008-02-05)
The inhibition of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) with three phenols was investigated. Phenol was an effective CA I-IV, IX, XII and XIV inhibitor (K(I)s of 2.7-11.5 microM) and a less effective one against the other isoforms, CA
Amy M Ruschak et al.
Journal of the National Cancer Institute, 103(13), 1007-1017 (2011-05-25)
The proteasome is an intracellular enzyme complex that degrades ubiquitin-tagged proteins and thereby regulates protein levels within the cell. Given this important role in maintaining cellular homeostasis, it is perhaps somewhat surprising that proteasome inhibitors have a therapeutic window. Proteasome
Xinliang Mao et al.
Toxicology letters, 182(1-3), 1-6 (2008-09-25)
5-Chloro-7-iodo-quinolin-8-ol (Clioquinol) is a halogenated 8-hydroxyquinoline that was used in 1950-1970s as an oral anti-parasitic agent for the treatment and prevention of intestinal amebiasis. However in the 1970s oral Clioquinol was withdrawn from the market due to reports of neurotoxicity
Jie Geng et al.
Advanced healthcare materials, 1(3), 332-336 (2012-11-28)
Metal ions play important roles in amyloid aggregation and neurotoxicity. Metal-ion chelation therapy has been used in clinical trials for Alzheimer's disease (AD) treatment. However, clinical trial studies have shown that long-term use of metal chelator can cause adverse side
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