5,7-dichloroquinolin-8-ol

• ChemBase ID: 1112
• Molecular Formular: C9H5Cl2NO
• Molecular Mass: 214.0481
• Monoisotopic Mass: 212.97481915
• SMILES: Clc1c2c(nccc2)c(O)c(Cl)c1
• Canonical SMILES: Clc1cc(Cl)c2c(c1O)nccc2
• InChI: InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H
• InChIKey: WDFKMLRRRCGAKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dichloroquinolin-8-ol
• IUPAC Traditional name: chloroxine
• Brand Name: Capitrol; Chlofucid; Clofuzid; Endiaron; Quesyl; Quinolor; Quixalin
• Synonyms: CHQ; Dichlorohydroxyquinoline; Dichloroquinolinol; Dichloroxin; Chloroxyquinoline; Chlorquinol; Dikhloroskin; Chloroxine; Capitrol; 5,7-Dichloro-8-hydroxyquinoline; 5,7-Dichloro-8-quinolinol; 5,7-Dichloro-8-quinolinol; Chloroxine; 5,7-DICHLORO-8-HYDROXYQUINOLINE; 5,7-Dichloroquinolin-8-ol; 5,7-Dichloro-8-hydroxyquinoline; 5,7-二氯-8-羟基氮杂萘; 氯喔星; 5,7-二氯-8-羟基喹啉

Database IDs

• CAS Number: 773-76-2
• EC Number: 212-258-3
• MDL Number: MFCD00006786
• Beilstein Number: 153606
• Merck Index: 142175
• PubChem SID: 46508620; 24894028; 160964575
• PubChem CID: 2722

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.954171
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.0114627
• LogD (pH = 7.4): 2.461107
• Log P: 3.0354245
• Molar Refractivity: 51.5698 cm^3
• Polarizability: 21.31888 Å^3
• Polar Surface Area: 33.12 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.44
• LOG S: -3.19
• Solubility (Water): 1.38e-01 g/l

PROPERTIES

Physical Property

• Melting Point: 178-180 °C(lit.); 180-182°C
• Hydrophobicity(logP): 3

Safety Information

• Storage Condition: -20°C; 2-8°C
• RTECS: VC5350000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41; 36/37/38; R:36/37/38
• Safety Statements: 26-36; 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335; H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: 97%; 98%; 99%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C9H5Cl2NO

DETAILS

MP Biomedicals - 02150867

Forms complexes enabling assay of microgram quantities of vanadium.
Tan to yellow crystals

MP Biomedicals - 05201983

MP Biomedicals Rare Chemical collection

DrugBank - DB01243

• Drug Groups: approved
• Description: Chloroxine is a synthetic antibacterial compound. Chloroxine is a compound used in some shampoos for the treatment of dandruff and seborrheic dermatitis of the scalp.
• Indication: Used in the treatment of dandruff and mild to moderately severe seborrheic dermatitis of the scalp.
• Pharmacology: Chloroxine has an antibacterial action, inhibiting the growth of gram-positive as well as some gram-negative organisms. Also, chloroxine has shown some antifungal activity against certain dermatophytes and yeasts.
• Toxicity: The toxicological properties of this material have not been investigated.
• Affected Organisms: Humans and other mammals
• References: Malaveille C, Brun G, Bartsch H: Genotoxicity of ochratoxin A and structurally related compounds in Escherichia coli strains: studies on their mode of action. IARC Sci Publ. 1991;(115):261-6. [Pubmed] ; Malaveille C, Brun G, Bartsch H: Structure-activity studies in E. coli strains on ochratoxin A (OTA) and its analogues implicate a genotoxic free radical and a cytotoxic thiol derivative as reactive metabolites. Mutat Res. 1994 May 1;307(1):141-7. [Pubmed]
• External Links: Drugs.com

Selleck Chemicals - S1839

Research Area: Inflammation, Infection
Biological Activity:
Chloroxine is a synthetic antibacterial compound that is effective in the treatment of dandruff and seborrheic dermatitis when incorporated in a shampoo. It is a halogenated hydroxyquinoline with antibacterial and antifungal properties similar to those of clioquinol. It is used topically in the treatment of dandruff and seborrhoeic dermatitis of the scalp. It has also been given orally in preparations for gastrointestinal disorders. It is a component of halquinol. [1]

Sigma Aldrich - D64600

Packaging
5, 100 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D64600.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Malaveille C, Brun G, Bartsch H: Genotoxicity of ochratoxin A and structurally related compounds in Escherichia coli strains: studies on their mode of action. IARC Sci Publ. 1991;(115):261-6. Pubmed
• Malaveille C, Brun G, Bartsch H: Structure-activity studies in E. coli strains on ochratoxin A (OTA) and its analogues implicate a genotoxic free radical and a cytotoxic thiol derivative as reactive metabolites. Mutat Res. 1994 May 1;307(1):141-7. Pubmed
• Pérez-Ruiz T et al. J Pharm Biomed Anal. 1996