General Description

Benzofuran-6-carboxylic acid is a yellow crystalline solid with low solubility in water and notable properties such as antimicrobial and antioxidant activity, as well as versatility in organic synthesis. It has various applications in high-performance liquid chromatography detection, pharmaceutical intermediate synthesis, and as a potential inhibitor of transglutaminases, making it an important compounyellowd in analytical chemistry, pharmaceutical synthesis, and therapeutic research. However, precautions must be taken when handling benzofuran-6-carboxylic acid as it poses safety hazards such as skin and eye irritation, respiratory irritation, and toxicity if ingested. Proper safety protocols should be followed to minimize any risks associated with handling and exposure to the substance.

Figure 1. Benzofuran-6-carboxylic acid

Properties

Benzofuran-6-carboxylic acid is an organic compound with the molecular formula C9H6O3. It belongs to the class of aromatic carboxylic acids and is characterized by a benzene ring fused with a furan ring, with a carboxylic acid group attached at the 6th position of the benzofuran ring. This compound possesses several notable properties. Firstly, it is a yellow crystalline solid that is sparingly soluble in water but readily soluble in common organic solvents such as ethanol and acetone. Benzofuran-6-carboxylic acid exhibits a melting point of around 158-162°C. It is important to highlight that this compound has potential biological activities. Some studies have suggested its antimicrobial properties, demonstrating inhibitory effects against certain bacteria and fungi. Additionally, benzofuran-6-carboxylic acid possesses antioxidant properties, which may contribute to its ability to scavenge free radicals and protect against oxidative stress. Moreover, this compound can serve as a versatile building block in organic synthesis due to the presence of both a carboxylic acid group and an aromatic ring. It can undergo various chemical transformations, allowing the introduction of functional groups and formation of more complex molecules. In summary, Benzofuran-6-carboxylic acid exhibits characteristics such as low solubility in water, antimicrobial and antioxidant properties, and versatility in organic synthesis, making it a compound of interest for both chemical and biological applications. ¹

Applications

Benzofuran-6-carboxylic acid has various applications in different fields. Firstly, it is used as a key component in a high-performance liquid chromatography detection method for lipalast or related substances in its preparations. This method effectively addresses the issue of undetectable related substances in lipalast or its preparations. Secondly, benzofuran-6-carboxylic acid plays a crucial role in the synthesis of methyl 3-hydroxy-4-((trimethylsilyl)ethynyl)benzoate, which is a pharmaceutical intermediate. Using this compound as a raw material, along with a palladium-loaded ordered mesoporous carbon catalyst and a cuprous iodide-triphenylphosphine complex, the catalytic synthesis of methyl 3-hydroxy-4-((trimethylsilyl)ethynyl)benzoate is significantly improved. The reaction time is shorter, the synthesis yield reaches 94%, and the obtained product demonstrates high purity and stability. Furthermore, benzofuran-6-carboxylic acid is also identified as a compound with potential as a novel inhibitor of transglutaminases. Transglutaminases, specifically transglutaminase 2, are associated with certain diseases. Therefore, benzofuran-6-carboxylic acid and its derivatives can be utilized in the production of pharmaceutical compositions aimed at the prophylaxis and treatment of transglutaminase-related diseases. In summary, benzofuran-6-carboxylic acid exhibits applications in high-performance liquid chromatography detection, pharmaceutical intermediate synthesis, and as a potential inhibitor of transglutaminases, suggesting its importance in analytical chemistry, pharmaceutical synthesis, and therapeutic research. ^2,3,4

Safety

Benzofuran-6-carboxylic acid poses certain safety hazards and precautions should be taken when handling it. The substance is considered harmful if swallowed, meaning ingestion can lead to adverse effects on health. Additionally, it has the potential to cause skin irritation upon contact, which suggests that protective measures, such as wearing gloves and lab coats, should be taken when working with it. Furthermore, benzofuran-6-carboxylic acid can cause serious eye irritation, making eye protection essential during handling. Lastly, it may also cause respiratory irritation, implying that adequate ventilation should be ensured in areas where the substance is used. Overall, proper safety protocols must be followed to minimize risks associated with handling and exposure to benzofuran-6-carboxylic acid. ⁵

Reference

1. Benzofuran-6-carboxylic acid. National Center for Biotechnology Information, 2023, PubChem Compound Summary for CID 17867234.

2. Inhibitors of transglutaminases. National Center for Biotechnology Information, 2023, PubChem Patent Summary for CA-3166252-A1.

3. Synthetic method of methyl 3-hydroxy-4-((trimethylsilyl)ethynyl)benzoate. National Center for Biotechnology Information, 2023, PubChem Patent Summary for CN-112625057-A.

4. A kind of lipalast or its preparation related substance detection method. National Center for Biotechnology Information,2023, PubChem Patent Summary for CN-114689733-A.

5. 1-Benzofuran-6-carboxylic acid. European Chemicals Agency, EC / List no. 815-384-2.