4-Nitrophenyl decanoate

Decanoic acid 4-nitrophenyl ester; 4-Nitrophenyl caprate

4-Nitrophenyl decanoate refers to a nitrophenyl ester that is commonly used as a substrate for enzymatic assays, especially in hydrolysis reactions. It is a colorless and crystalline compound that is soluble in organic solvents like ethyl acetate, dichloromethane, and chloroform. Due to its unique properties, the compound has found applications in various fields of research and industry. This paper aims to provide a comprehensive review of 4-nitrophenyl decanoate, including its properties, synthesis, applications, and future directions.

Background:

Esters are organic compounds that are commonly prepared via reaction between carboxylic acids and alcohols. They are widely used in various fields, including chemistry, medicine, and industry. The esterification process is usually catalyzed by an acid catalyst, and the reaction is typically exothermic. Among the various types of esters, nitrophenyl esters are particularly notable due to their ability to serve as substrates for enzymatic assays. In particular, 4-nitrophenyl decanoate has attracted a lot of interest in recent years due to its unique properties.

Physical and Chemical Properties:

4-Nitrophenyl decanoate is a white or yellowish crystalline powder that has a melting point of 49-51°C. It has a molecular weight of 345.44 g/mol and a boiling point of 432.2°C at 760 mmHg. The compound is sparingly soluble in water (0.019 mg/L at 25°C) and highly soluble in organic solvents like ethanol, methanol, and acetone. Its solubility in chloroform is estimated to be 20 g/L at 20°C. The compound is stable under standard conditions of temperature and pressure and has a shelf-life of at least two years.

Synthesis and Characterization:

4-Nitrophenyl decanoate can be synthesized via esterification reaction between 4-nitrophenol and decanoic acid in the presence of an acid catalyst, such as sulfuric acid or hydrochloric acid. The reaction is typically carried out at elevated temperature (around 60-70°C) and requires careful handling due to the exothermic nature of the reaction. The resulting product is purified by recrystallization or column chromatography to obtain pure 4-nitrophenyl decanoate.

The compound can be characterized by various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry (MS). NMR spectroscopy is particularly useful for identifying the structural features of the compound, while IR spectroscopy can be used to identify the functional groups present in the compound. MS can provide information about the molecular weight and fragmentation patterns of the compound.

Analytical Methods:

4-Nitrophenyl decanoate is commonly used as a substrate for enzymatic assays, particularly in hydrolysis reactions. The hydrolysis of the compound results in the formation of 4-nitrophenol, which can be detected spectrophotometrically at a wavelength of 405 nm. The rate of hydrolysis can be measured by monitoring the increase in absorbance at 405 nm over time.

Other analytical methods that have been used to quantify 4-nitrophenyl decanoate include high-performance liquid chromatography (HPLC) and thin-layer chromatography (TLC). HPLC is particularly useful for separating and quantifying the compound from other impurities or reaction products.

Biological Properties:

4-Nitrophenyl decanoate has been widely used as a substrate for various enzymes, including lipases, esterases, and proteases. The compound is particularly useful for studying the kinetics and specificity of these enzymes. For example, it has been used to study the activity of lipases in various matrices, such as milk, cheese, and vegetable oils. The activity of the enzymes can be measured by monitoring the release of 4-nitrophenol from the hydrolysis reaction.

Toxicity and Safety in Scientific Experiments:

Although 4-nitrophenyl decanoate is generally considered to be a safe and stable compound, it can pose a health hazard if handled improperly. The compound may cause skin irritation or respiratory irritation upon exposure. Therefore, it is important to follow appropriate safety precautions, such as wearing gloves and protective clothing, and working in a well-ventilated area. The compound should be stored in a cool and dry place, away from sources of heat or ignition.

Applications in Scientific Experiments:

4-Nitrophenyl decanoate has found widespread applications in various fields of research and industry. Some of the notable applications include:

- Enzymatic assays: The compound is commonly used as a substrate for various enzymes, including lipases, esterases, and proteases. The hydrolysis of the compound can be used to study the kinetics and specificity of these enzymes.

- Organic synthesis: 4-Nitrophenyl decanoate can be used as a building block for the synthesis of other compounds, such as nitrophenylalanine and 4-nitrophenyl acetate.

- Drug discovery: The compound can be used as a model substrate for screening potential drugs or inhibitors that target specific enzymes.

- Biotechnology: The compound can be used as a reporter substrate for monitoring gene expression in bacterial or yeast cells.

Current State of Research:

The research on 4-nitrophenyl decanoate has been focused mainly on its applications in enzymatic assays and organic synthesis. However, there is still much to be explored in terms of its potential applications in other fields, such as drug discovery, biotechnology, and materials science. Moreover, there is a need for more detailed studies on its toxicity and safety in scientific experiments.

Potential Implications in Various Fields of Research and Industry:

Given its unique properties, 4-nitrophenyl decanoate has the potential to find applications in various fields of research and industry. Some of these potential implications include:

- Drug discovery: The compound can be used as a model substrate for screening potential drugs or inhibitors that target specific enzymes. It can also be used as a tool for studying the mechanism of action of existing drugs.

- Biotechnology: The compound can be used as a reporter substrate for monitoring gene expression in bacterial or yeast cells. It can also be used as a tool for engineering enzymes with desired activities or specificities.

- Materials science: The compound can be used as a building block for the synthesis of materials with specific properties, such as polymers or surfactants.

- Environmental science: The compound can be used as an indicator of esterase activity in soil or water samples, which can provide insights into the biodegradability of organic contaminants.

Limitations and Future Directions:

Despite its potential applications, 4-nitrophenyl decanoate has some limitations that need to be addressed in future research. Some of these limitations include:

- Limited solubility in water: The compound has limited solubility in water, which can limit its applications in certain assays or experiments.

- Limited specificity: The compound may not be suitable for studying enzymes that have high substrate specificity, as it may be hydrolyzed by other enzymes present in the sample.

- Limited stability: The compound may undergo hydrolysis or decomposition over time, which can affect the accuracy of enzymatic assays.

To address these limitations, future research should focus on developing more stable and specific substrates for enzymatic assays, as well as exploring the potential of 4-nitrophenyl decanoate in other fields, such as drug discovery, biotechnology, and materials science. Some of the future directions for research on 4-nitrophenyl decanoate include:

- Developing more stable and specific substrates for enzymatic assays.

- Identifying new enzymes that can hydrolyze 4-nitrophenyl decanoate with high specificity.

- Developing new applications for 4-nitrophenyl decanoate in drug discovery, biotechnology, and materials science.

- Investigating the environmental fate and toxicity of 4-nitrophenyl decanoate and its derivatives.

- Improving the synthesis and purification methods for 4-nitrophenyl decanoate to obtain high-purity and high-yield products.

Conclusion:

4-Nitrophenyl decanoate is a unique compound that has found applications in various fields of research and industry, particularly as a substrate for enzymatic assays. However, there is still much to be explored in terms of its potential applications and limitations, as well as its toxicity and safety in scientific experiments. Future research should focus on developing more stable and specific substrates for enzymatic assays, as well as exploring the potential of 4-nitrophenyl decanoate in other fields, such as drug discovery, biotechnology, and materials science.

4-Nitrophenyl decanoate is a fatty acid ester that belongs to the class of lipids. It is made up of a 4-nitrophenyl group, which is bound to an acyl chain through an ester linkage. The 4-nitrophenol group reacts with the butyrate group in the presence of a base and catalyst to form the product. 4-Nitrophenyl decanoate has been shown to have high concentrations in human serum and bacterial cells. This chemical has been used as a model system for studying enzyme activities, such as kinetic and structural analysis, and its role in bacterial cell metabolism. 4-Nitrophenyl decanoate also serves as a substrate for acyl coenzyme A dehydrogenase, which catalyzes the conversion of this compound into acetoacetyl CoA.