8-hydroxyquinoline ( hydroxyquinoline , oxin ) is a heterocyclic organic compound of composition C 9 H 7 NO. In medicine, oxyquinoline was previously often used as an antimicrobial agent (a group of oxyquinolines ).
8-oxyquinoline | |
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Are common | |
| Chem. formula | C₉H₇NO |
Classification | |
| CAS number | |
| Pubchem | |
| Chemspider | |
| EINECS number | 205-711-1 |
| CHEBI | 48981 |
| Drugbank | |
SMILES | |
C1 = CC2 = C (C (= C1) O) N = CC = C2 | |
Inchi | |
1S / C9H7NO / c11-8-5-1-3-7-4-2-6-6-10-9 (7) 8 / h1-6,11H | |
| Data are given for standard conditions (25 ℃, 100 kPa) , unless otherwise specified. | |
Content
Physical Properties
Light yellow crystals ; t PL 75 - 76 ° C , t kip 267 ° C ; soluble in organic solvents: in chloroform 382 g / l, in benzene 319 g / l, in isoamylacetate 174 g / l, ethyl ether 96 g / l, isoamyl alcohol 56.6 g / l; in alkalies and acids , in water - poorly (minimum solubility of 0.53 g / l at the isoelectric point ( pH = 7.2)). Easily volatile with water vapor. Solutions of 8-hydroxyquinoline darken in the light, so they should be stored in a dark cool place.
Getting
Obtained by heating o-aminophenol hydrochloride and o-nitrophenol , glycerol and sulfuric acid (modification of ) or by alkaline melting of 8-quinoline sulfonic acid.
Application
8-hydroxyquinoline forms complex compounds with more than 40 elements of the periodic system and is a low-selective group reagent . The ability of 8-hydroxyquinoline to form with many metal cations poorly soluble in aqueous solutions ( acetic acid , ammonia , etc.) crystalline complex chelate salts , for example, Mg (C 9 H 6 ON) 2 , Al (C 9 H 6 ON) 3 , It is used in practice for the determination and separation of a number of metals ( Al , Zn , Cd , Mg , etc.).
Hydroxyneiolinates of different metals differ in color and can be determined photometrically . Good solubility in chloroform is used for the extraction-photometric determination of a number of elements.
Some 8-hydroxyquinoline derivatives are used as fungicides [for example, copper salt (C 9 H 6 ON) 2 Cu] and antiseptics of amebotsidno and external action.
The 8-hydroxyquinoline complex with aluminum is used to make organic light emitting diodes (OLED). Variations of substituents in the quinoline core allow the production of materials with different luminescent properties. [one]
Medical use
Oxyquinoline is indicated for disinfecting hands, treating wounds, ulcers, mycoses . For processing a surgical instrument is unsuitable, as it interacts with the metal.
When applied to the skin, a long-term antifungal effect (96 hours) on the skin surface is provided. It is active against various types of dermatophytes (the genus Trichophyton, microsporum, yeast-like fungi, fungi of the genus Penicillium and Aspergilus, and other pathogens). Relatively low toxic, no local irritant and is not inactivated by tissue proteins.
For disinfection of hands, washing of wounds, ulcers, douching, hydroxyquinoline is used at a dilution of 1: 1000, 1: 2000. When mycosis - externally, in the form of applications on the affected skin and nail beds after removal of the nail plates. The plaster of the desired size and shape is applied with a sticky surface to the skin or nail beds, previously lightly moistened with water, pressed to ensure that the entire area of the plaster contacts the affected area. The duration of a one-time application is no more than 4 days, then the plaster is changed, conducting hygienic procedures in the interval between applications. After the third application (12 days later), patients are cleaned with horny layers using a soap-soda bath. The treatment is carried out under the control of the growth of the nail plate and microscopic examination for fungi until at least 3 negative analyzes are obtained with an interval of 1 month. The duration of treatment depends on the time of regrowth of healthy nail plates and ranges from 3 to 10-12 months.
Currently, oxyquinoline-based drugs are not registered in Russia.
Literature
"Chemical Encyclopedia". - Ed. Knunyantsa L.I. - M .: Great Russian Encyclopedia, 1992, V.3, p.361
Notes
- ↑ Montes, VA; Pohl, R .; Shinar, J .; Anzenbacher, P. Jr. Effective Manipulation on the Emission of 5-Substituted Tris (8-quinolinolate) Aluminum (III) Complexes (Eng.) // Chemistry - A European Journal : journal. - 2006. - Vol. 12 , no. 17 - P. 4523–4535 . - DOI : 10.1002 / chem.200501403 .