Why Is 5-Chloro-8-Hydroxyquinoline a Key Compound in Antimicrobial Research?
Technical Introduction
5-Chloro-8-Hydroxyquinoline is a chlorinated quinoline derivative with the molecular formula C₉H₆ClNO.
It belongs to the class of hydroxyquinolines, compounds known for their metal-chelating and biological activity.
The presence of the hydroxyl group at position 8 and the chlorine substituent at position 5 enhances its antimicrobial spectrum and stability.
It appears as a yellow to pale crystalline solid and is sparingly soluble in water but soluble in organic solvents such as ethanol and chloroform.
Applications
1. Pharmaceutical Industry
Active ingredient in topical antimicrobial creams, ointments, and eye drops.
Used in formulations for treating skin infections, eczema, and fungal conditions.
2. Antimicrobial Agent
Effective against Gram-positive and Gram-negative bacteria, as well as certain fungi.
Exhibits protozoocidal activity, making it useful in antiparasitic research.
3. Metal Chelation
Forms stable complexes with metals, applicable in analytical chemistry for metal detection.
4. Research and Development
Studied for its antiviral, anticancer, and anti-inflammatory potential.
Advantages
Broad Antimicrobial Spectrum: Active against bacteria, fungi, and protozoa.
Chemical Stability: Chlorine substitution enhances durability in formulations.
Chelating Properties: Useful in both medicinal and analytical applications.
Multiple Formulation Options: Can be incorporated into ointments, creams, solutions, and suspensions.
Typical Parameters
| Property | Value |
|---|---|
| Chemical Formula | C₉H₆ClNO |
| Molecular Weight | 179.60 g/mol |
| CAS Number | 130-16-5 |
| Appearance | Yellow to pale crystalline solid |
| Purity (%) | ≥98.0 |
| Melting Point (°C) | 155–157 |
| Solubility | Slightly soluble in water, soluble in ethanol, chloroform |
| Storage | Store in cool, dry, well-ventilated place, away from light |
| Stability | Stable under recommended storage conditions |
| Shelf Life | 24 months (sealed) |
FAQs
Q1: Is 5-Chloro-8-Hydroxyquinoline safe for human use?
A1: It is approved for topical use in certain concentrations but should not be ingested without medical supervision.
Q2: Can it be used in agriculture?
A2: Yes, it has been explored as a plant protection agent against microbial pathogens.
Q3: How does the chlorine atom improve activity?
A3: Chlorine enhances lipophilicity and stability, improving penetration into microbial cells.
Q4: Is it soluble in water?
A4: It has low water solubility but dissolves well in organic solvents.
Q5: What is its primary mode of antimicrobial action?
A5: It interferes with microbial enzyme systems, likely through metal ion chelation.
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