Transformation of Myristicin Isolate from Nutmeg Seed Essential Oil into Substituted 1,3 Benzodioxole Precursor of the Flavone Kanugin
Arvia Hafisah, Budi Arifin, Luthfan Irfana, Verucha Fauzia Putri

Department of Chemistry, Faculty of Mathematics and Natural Sciences, IPB University

Abstract

Indonesia is the worlds largest producer of nutmeg, and most of it is exported as seeds, mace, and essential oil. Nutmeg seed essential oil contains myristicin as its primary constituent, a methoxy substituted allylbenzene fused with a 1,3 benzodioxole ring. Several studies have reported the antidepressant and antiproliferative activities of 1,3 benzodioxole substituted chalcones. Additionally, flavone kanugin, which has a similar 1,3 benzodioxole structure, has been shown to have antioxidant and anticancer properties. Kanugin flavone has not been extensively synthesized, and the reported synthetic route does not involve 1,3 benzodioxole substituted chalcone precursors. The purpose of this study was to isolate myristicin from nutmeg seed essential oil and then synthesize 1,3 benzodioxole substituted chalcones as precursors to kanugin flavone from this isolate. Commercial nutmeg oil was subjected to fractional vacuum distillation, and myristicin was purified from the resulting myristicin rich fraction using preparative thin layer chromatography. This approach successfully isolated myristicin with a purity of 98%. Myristicin was isomerized using KOH to produce isomyristicin. This was subsequently oxidized with KMnO4 and Tween 80 as a catalyst to yield myristicinaldehyde. In a basic medium, the Claisen Schmidt condensation reaction between myristicinaldehyde and 2 hydroxyacetophenone produces a substituted 1,3 benzodioxole chalcone compound, which is a precursor to flavone kanugin. Chromatography and spectroscopy were used to confirm the myristicin isolate and reaction products at each stage. The findings of this study are intended to increase the value of Indonesian nutmeg commodities and provide information on the synthesis of flavonoids with a 1,3 benzodioxole structure.

Keywords: Chalcone- Essential oil- Flavonoid- Myristicin- Nutmeg

Topic: Organics Chemistry