Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
[CAS# 161797-99-5]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
• Synonyms: Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate
• Molecular Formula: C₁₃H₁₃NO₃S
• Molecular Weight: 263.31
• CAS Registry Number: 161797-99-5
• EC Number: 605-268-8
• SMILES: CCOC(=O)C1=C(N=C(S1)C2=CC=C(C=C2)O)C

Properties

• Density: 1.274
• Melting point: 180 °C

Safety Data

• Hazard Symbols: GHS05 Danger
• Risk Statements: H318
• Safety Statements: P264+P265-P280-P305+P354+P338-P317

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, commonly referred to as methylthiazole carboxylate, was first synthesized through organic synthesis endeavors aimed at exploring the chemical reactivity and potential applications of thiazole derivatives. The discovery of this compound can be traced back to the mid-20th century when chemists were investigating methods to functionalize thiazole rings with various substituents. By reacting 4-hydroxyphenylacetic acid with thioamide and ethyl chloroacetate, researchers successfully synthesized ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate. This compound's discovery opened avenues for further research into its chemical properties and potential applications in pharmaceuticals, agrochemicals, and materials science.

Thiazole derivatives, including ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, have demonstrated antimicrobial properties against a wide range of bacterial and fungal pathogens. These compounds inhibit microbial growth by interfering with essential biological processes, such as cell wall synthesis or protein function, making them valuable candidates for the development of antimicrobial drugs. Thiazole carboxylates possess antioxidant properties due to their ability to scavenge reactive oxygen species (ROS) and prevent oxidative damage to biomolecules. This antioxidant activity is attributed to the presence of the phenolic hydroxyl group in the 4-hydroxyphenyl moiety, which enhances the compound's free radical scavenging capacity.

Thiazole carboxylates are utilized in the development of agrochemicals, including insecticides, fungicides, and herbicides. These compounds exhibit pesticidal activity against various pests and plant pathogens, contributing to crop protection and yield enhancement in agriculture. Thiazole-based pesticides offer advantages such as broad-spectrum activity, low environmental persistence, and reduced toxicity to non-target organisms. Some thiazole derivatives, including ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, have been investigated for their potential as plant growth regulators (PGRs). These compounds modulate physiological processes in plants, such as seed germination, root development, and flowering, leading to improved crop productivity and stress tolerance.

Thiazole derivatives have fluorescent properties that make them useful as fluorescent probes in materials science and bioimaging applications. Ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate and its derivatives can be incorporated into fluorescent dyes and sensors for detecting analytes, monitoring chemical reactions, and imaging biological systems. Thiazole carboxylates are employed as additives in polymer materials to impart desirable properties, such as UV stability, flame retardancy, and antimicrobial activity. These compounds enhance the performance and durability of polymers used in various applications, including packaging, textiles, and electronics.

Ongoing research focuses on exploring the pharmacological potential of ethyl 2-(4-hydroxyphenyl)-4-methylthiazole-5-carboxylate and its derivatives for the treatment of infectious diseases, cancer, and neurodegenerative disorders. Rational drug design approaches aim to optimize the compound's pharmacokinetic properties, target selectivity, and therapeutic efficacy through structure-activity relationship studies and computational modeling. In agriculture, efforts are underway to develop novel thiazole-based pesticides with improved efficacy, environmental safety, and resistance management properties. Research initiatives explore new synthetic routes, formulation technologies, and application methods to enhance the performance and sustainability of thiazole-derived agrochemicals.

References

2020. Design, synthesis, cytotoxic evaluation and molecular docking studies of novel thiazolyl α-aminophosphonates. Research on Chemical Intermediates, 47(2), 567-583.
DOI: 10.1007/s11164-020-04321-6