Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation

Annisa Mustika Pertiwi, Deana Wahyuningrum

Abstract


Dehydrozingerone (DHZ), 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, is a natural compound found in the rhizome of ginger (Zingiber officinale) plant that offers wide range of bioactivities including antioxidants, anticancer, antimalarial, antidepressant, antifungal, and many others. The synthesis of DHZ can be achieved through the cross-aldol Claisen-Schmidt condensation of vanillin and acetone. However, the conventional method of DHZ synthesis requires 48-hours reaction time, generates low yield product percentage, and excessive use of volatile organic solvents for the purification process. To address these limitations, the green synthesis method of DHZ in 1-decyl-3-methylimidazolium bromide ([DMIM]Br) ionic liquid medium utilizing Microwave Assisted Organic Synthesis (MAOS) method are conducted in this research. The result showed that the addition of ionic liquid affects the purity of the DHZ product obtained. Product characterization was carried out using melting point tests, TLC, 1H (500 MHz, CDCl3) and 13C (125 MHz, CDCl3) NMR instrumentation. The DHZ product with the best yield was synthesized from vanillin and acetone (1:10, mol/mol) in NaOH 2.5 M and 5% [DMIM]Br (w/v) using MAOS for 120 minutes (50 oC, 300 W) to produce a 62.96% yield product in the form of a bright yellow solid with a melting point range of 128-129 oC.


Keywords


Dehydrozingerone, Green Chemistry, Ionic Liquid, Microwave Synthesis

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DOI: http://dx.doi.org/10.30870/educhemia.v9i1.24414

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