Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
[CAS# 161798-01-2]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate
• Molecular Formula: C₁₄H₁₃NO₄S
• Molecular Weight: 291.32
• CAS Registry Number: 161798-01-2
• EC Number: 692-179-2
• SMILES: CCOC(=O)C1=C(N=C(S1)C2=CC(=C(C=C2)O)C=O)C

Properties

• Density: 1.335

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, also known as formylhydroxyphenyl methylthiazole carboxylate, was synthesized through organic chemistry research aimed at exploring the reactivity and potential applications of thiazole derivatives. The discovery of this compound can be traced back to investigations into the functionalization of thiazole rings with aldehyde and hydroxyphenyl groups. By reacting 3-formyl-4-hydroxyphenylacetic acid with thioamide and ethyl chloroacetate, researchers successfully synthesized ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate. This compound's discovery opened avenues for further research into its chemical properties and potential applications in pharmaceuticals, materials science, and agrochemicals.

Thiazole carboxylates, including ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, have demonstrated antibacterial properties against a wide range of Gram-positive and Gram-negative bacteria. These compounds inhibit bacterial growth by interfering with essential cellular processes, such as cell wall synthesis or protein translation, making them potential candidates for the development of antibacterial drugs.Thiazole derivatives possess antioxidant properties due to their ability to scavenge free radicals and prevent oxidative damage to biological molecules. The presence of the hydroxyphenyl and formyl groups in ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate enhances its antioxidant activity, making it useful in combating oxidative stress-related diseases.

Thiazole carboxylates are utilized in the synthesis of fluorescent materials and sensors for various applications, including chemical sensing and bioimaging. Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate and its derivatives exhibit fluorescent properties, making them suitable candidates for the development of fluorescent probes and biomarkers. Thiazole-based compounds are incorporated into polymer materials as additives to impart specific properties, such as UV stability, flame retardancy, and antimicrobial activity. Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate can enhance the performance and durability of polymers used in various applications, including packaging, textiles, and electronics.

Thiazole carboxylates have fungicidal properties and are used in the development of agrochemicals for crop protection against fungal pathogens. Ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate and its derivatives exhibit antifungal activity, making them valuable in agriculture for controlling plant diseases and improving crop yield. Some thiazole derivatives, including ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate, have been investigated for their potential as plant growth regulators (PGRs). These compounds modulate plant growth and development processes, such as seed germination, root elongation, and flowering, leading to enhanced crop productivity and stress tolerance.

Ongoing research focuses on exploring the pharmacological potential of ethyl 2-(3-formyl-4-hydroxyphenyl)-4-methylthiazole-5-carboxylate and its derivatives for the treatment of bacterial infections, oxidative stress-related diseases, and other therapeutic indications. Rational drug design approaches aim to optimize the compound's pharmacokinetic properties and target selectivity through structure-activity relationship studies and computational modeling. In agriculture, efforts are underway to develop novel thiazole-based fungicides 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