Ultrasonic Assisted Synthesis of 1,5-Bis(3'-ethoxy-4'-hydroxyphenyl)-1,4-pentadiene-3-one: Effect of Time and Temperature

Abstract

The compound 1,5-bis(3′-ethoxy-4′-hydroxyphenyl)-1,4-pentadiene-3-one (EHP), an analog of curcumin, displays significant antioxidant, anti-inflammatory and antibacterial properties. Synthesized through an aldol condensation reaction, EHP modifies the structure of curcumin by substituting methoxy groups with ethoxy groups and converting diketones to monoketone. This study explores the influence of time and temperature on the ultrasonic-assisted synthesis of 1,5-bis(3′-ethoxy-4′-hydroxyphenyl)-1,4-pentadiene-3-one (EHP). The synthesis process involved precise measurements and controlled conditions to achieve the desired compound. Through a series of experiments conducted at varying temperatures and irradiation times, the synthesis yield and purity of EHP were evaluated. Analysis techniques including thin layer chromatography (TLC), densitometry, ultraviolet-visible (UV-vis) spectrophotometry, Fourier-transform infrared spectroscopy (FTIR), liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy were employed to characterize the EHP compound. The results indicate the sensitivity of EHP synthesis to reaction conditions, it reduce synthesis time (10 min) with improve the product yield (87.17%) at moderate temperature (30 ºC). The findings provide valuable insights into optimizing synthesis conditions for enhanced product quality.