The Synthesis of Dehydrozingerone (DHZ) in 1-Decyl-3-Methylimidazolium Bromide ([DMImBr]) Ionic Liquid Medium Utilizing Microwave Assisted Organic Synthesis (MAOS) Method
Annisa Mustika Pertiwi (a), Deana Wahyuningrum (a)*

(a) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung
Jalan Ganesha 10, Bandung 40132, Indonesia
*deana[at]itb.ac.id

Abstract

Dehydrozingerone (DHZ), 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, is a natural compound that can be isolated from the rhizome of ginger (Zingiber officinale) and has attracted the attention of many researchers, especially in the field of medicinal chemistry. DHZ and its derivatives have a wide range of bioactivities, including antioxidants, anticancer, antimalarial, antidepressant, antifungal, and many others. DHZ can be synthesized from vanillin and acetone by cross-aldol (Claisen-Schmidt) condensation, yet its conventional synthesis needs a 24-hour time and generates a low yield percentage. Green chemistry aspects such as efficiency, atom economy and low energy factor are important aspects that should be considered to synthesize DHZ. In this research, the synthesis of DHZ from vanillin and acetone in 1-decyl-3-methylimidazolium bromide ([DMIMBr]) ionic liquid media was carried out using the Microwave Assisted Organic Synthesis (MAOS) method as one of the synthesis methods that fulfill green chemistry aspects. Product characterization was carried out using melting point tests, TLC, FTIR, 500 MHz (1H) and 125 MHz (13C) NMR instrumentation. The DHZ product with the best yield was synthesized from vanillin and acetone (1:10, mol/mol) in 10% NaOH and 10% DMIMBr using MAOS (closed vessel) for 120 minutes (50 oC, 300 W) to produce a product in the form of a bright yellow solid of 60.90% yields with a melting point range of 128-129oC.

Keywords: Dehydrozingerone- Ionic Liquid- MAOS- Green Chemistry

Topic: CHEMISTRY AND MATERIAL SCIENCES