6-Chloro-3-indoxyl butyrate
[CAS# 159954-34-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Indoles
• Name: 6-Chloro-3-indoxyl butyrate
• Synonyms: (6-chloro-1H-indol-3-yl) butanoate
• Molecular Formula: C₁₂H₁₂ClNO₂
• Molecular Weight: 237.68
• CAS Registry Number: 159954-34-4
• SMILES: CCCC(=O)OC1=CNC2=C1C=CC(=C2)Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Discovory and Applicatios

6-Chloro-3-indoxyl butyrate is a chemical derivative of indoxyl compounds, characterized by the substitution of a chlorine atom at the 6-position of the indole ring and esterification with butyric acid. This compound belongs to a class of molecules often used as substrates in enzymatic assays, particularly for the detection of enzyme activities such as those of esterases or β-glucosidases.

The discovery of 6-chloro-3-indoxyl butyrate is linked to the broader development of chromogenic substrates based on indoxyl derivatives. Indoxyl esters have been widely studied and utilized due to their ability to release colored or fluorescent products upon enzymatic hydrolysis, enabling the visual or spectrophotometric detection of enzymatic activity. The introduction of a chlorine substituent at the 6-position alters the electronic properties of the molecule, which can influence the reactivity and detection sensitivity in biochemical assays.

Applications of 6-chloro-3-indoxyl butyrate primarily center on its use as a diagnostic reagent in microbiology and biochemistry. It serves as a substrate in colorimetric enzyme assays where the cleavage of the ester bond by specific enzymes results in the release of 6-chloro-3-indoxyl, which subsequently undergoes oxidation to form colored indigoid compounds. This color change provides a convenient and sensitive method for identifying enzyme presence and activity, often employed in bacterial identification and characterization.

In analytical biochemistry, 6-chloro-3-indoxyl butyrate is valuable for studying esterase activity in various biological samples, including tissues and microbial cultures. Its specificity and the distinct colorimetric response it produces allow for quantitative and qualitative analyses, facilitating research into enzyme kinetics and the screening of enzyme inhibitors.

The compound’s role extends to environmental and clinical microbiology, where it aids in the detection of particular bacterial enzymes linked to pathogenicity or biodegradation processes. By providing a reliable and easy-to-interpret enzymatic assay, 6-chloro-3-indoxyl butyrate contributes to diagnostic protocols and biochemical research methods.

Overall, 6-chloro-3-indoxyl butyrate is a chemically modified indoxyl ester used predominantly as a chromogenic substrate in enzymatic assays. Its development enhances the toolkit available for enzyme detection and characterization, with applications spanning microbiology, biochemistry, and diagnostic sciences.