FAQ

2,5-Dihydroxycinnamic acid methyl ester, also known as Methyl 2,5-dihydroxycinnamate, is a chemical compound with the molecular formula C₁₀H₁₀O₄ and a molecular weight of approximately 194.18 g/mol. It is a derivative of cinnamic acid, featuring a methyl ester group and two hydroxyl groups at the 2 and 5 positions of the phenyl ring.

Properties

• Appearance: Typically exists as a yellow crystalline solid.
• Melting Point: Ranges from 178°C to 180°C.
• Solubility: Solubility in water and other solvents is not explicitly defined but is generally considered to have moderate solubility in organic solvents.
• Stability: Should be stored at -20°C to maintain stability and avoid degradation.

Biological Activity

• EGFR Inhibition: Acts as a stable and effective inhibitor of the epidermal growth factor receptor (EGFR) tyrosine kinase activity. This makes it relevant in the study of signal transduction pathways and cancer research, where EGFR overactivation is associated with tumor growth and progression.
• Erbstatin Analog: Structurally similar to erbstatin, a known tyrosine kinase inhibitor, 2,5-dihydroxycinnamic acid methyl ester shares similar inhibitory properties, making it a valuable tool in biochemical and pharmacological research.

Applications

• Research Use: Primarily utilized in biochemical and pharmacological studies to investigate the role of EGFR in cellular processes and as a potential lead compound for developing anti-cancer agents.
• Synthetic Chemistry: Serves as a synthetic intermediate in the preparation of more complex molecules with potential biological activities.

Safety and Handling

• Toxicity: Classified as toxic, with potential hazards including acute toxicity via ingestion, inhalation, or skin contact.
• Handling Precautions: Requires careful handling under appropriate safety conditions, including the use of personal protective equipment (PPE) and adherence to proper disposal guidelines to prevent environmental contamination.

Synthesis

• The synthesis of 2,5-dihydroxycinnamic acid methyl ester typically involves the esterification of 2,5-dihydroxycinnamic acid with methanol in the presence of an acid catalyst. This reaction yields the methyl ester derivative, which can be purified through recrystallization or chromatography.