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• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Isoquinoline-5-carboxylic Acid (CAS No. 27810-64-6): An Overview of Its Structure, Properties, and Applications in Modern Research

Isoquinoline-5-carboxylic acid (CAS No. 27810-64-6) is a versatile organic compound that has garnered significant attention in recent years due to its unique chemical structure and potential applications in various fields, including medicinal chemistry, materials science, and analytical chemistry. This compound is characterized by its isoquinoline ring system, which is a fused benzene and pyridine ring, and a carboxylic acid functional group at the 5-position. The combination of these structural features imparts Isoquinoline-5-carboxylic acid with a range of chemical and physical properties that make it an attractive candidate for both fundamental research and practical applications.

The molecular formula of Isoquinoline-5-carboxylic acid is C₁₁H₈NO₂, with a molecular weight of approximately 184.19 g/mol. The compound is typically obtained as a white crystalline solid, which is soluble in common organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO). Its melting point is reported to be around 205-207°C, making it suitable for various thermal processes without significant decomposition.

In the realm of medicinal chemistry, Isoquinoline-5-carboxylic acid has been the subject of extensive research due to its potential biological activities. Recent studies have highlighted its role as a scaffold for the development of novel therapeutic agents. For instance, derivatives of Isoquinoline-5-carboxylic acid have shown promising anti-inflammatory and anti-cancer properties. A study published in the Journal of Medicinal Chemistry in 2021 reported that certain derivatives of this compound exhibited selective inhibition of cyclooxygenase-2 (COX-2), an enzyme implicated in the inflammatory response. This finding suggests that Isoquinoline-5-carboxylic acid could serve as a lead compound for the development of new anti-inflammatory drugs with reduced side effects compared to traditional nonsteroidal anti-inflammatory drugs (NSAIDs).

Beyond its potential as a therapeutic agent, Isoquinoline-5-carboxylic acid has also found applications in materials science. Its ability to form stable complexes with various metal ions makes it a valuable ligand for the synthesis of coordination polymers and metal-organic frameworks (MOFs). These materials have shown promise in areas such as gas storage, catalysis, and drug delivery. A notable example is the use of Isoquinoline-5-carboxylic acid-based MOFs for the selective adsorption and separation of carbon dioxide from flue gases, which is crucial for carbon capture and storage technologies.

In analytical chemistry, Isoquinoline-5-carboxylic acid has been utilized as a derivatizing agent for the detection and quantification of various analytes. Its carboxylic acid group can react with primary amines to form stable amides, which can be detected using techniques such as high-performance liquid chromatography (HPLC) and mass spectrometry (MS). This property has been leveraged in the development of sensitive and selective methods for the analysis of amino acids, peptides, and other biomolecules. A recent study published in the Analytical Chemistry journal demonstrated the use of Isoquinoline-5-carboxylic acid-derived amides for the rapid detection of trace levels of amino acids in complex biological matrices.

The synthesis of Isoquinoline-5-carboxylic acid can be achieved through several routes, each offering different advantages in terms of yield, purity, and scalability. One common method involves the condensation of 4-chlorobenzaldehyde with ethyl acetoacetate followed by cyclization under acidic conditions to form the isoquinoline ring. Subsequent oxidation steps are then used to introduce the carboxylic acid group at the 5-position. Advances in green chemistry have also led to the development of more environmentally friendly synthetic methods that minimize waste generation and reduce energy consumption.

In conclusion, Isoquinoline-5-carboxylic acid (CAS No. 27810-64-6) is a multifaceted compound with a wide range of applications in modern research. Its unique chemical structure endows it with valuable properties that make it suitable for use in medicinal chemistry, materials science, and analytical chemistry. Ongoing research continues to uncover new possibilities for this compound, further solidifying its importance in various scientific disciplines.

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• 7250-53-5(Quinoline-5-carboxylic acid)
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