Transformation of Eugenol into Coniferyl Ester for Synthesis of Podophyllotoxin Derivative

• Main Author: Siti Khodijah - Nim: 10513046 , Ikeu
• Format: Final Project
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/27954
• Institution: Institut Teknologi Bandung

<p align="justify">Indonesia is the country with abudant resources, including a number of essential oil plants, such as clove plant. The production of clove oil in Indonesia is one of the largest in the world. The main component in clove oil is eugenol (4-allyl-2-methoxyphenol). Eugenol (1) has functional groups of methoxy, hydroxy, and allyl, which can be transformed into other functional group to generate eugenol derivative compounds which have different bioactivities, such as Podophyllotoxin. Podophyllotoxin is a lignan compound that can be isolated from Podophyllum peltatum which has bioactivity as an anticancer drug. Eugenol can be transformed into coniferyl ester for synthesis of podophyllotoxin derivative compounds. The transformation of eugenol into coniferyl ester was carried out through protection of hydroxyl group, halogenation, and dehydrohalogenation reaction. The protection reaction of phenol group of eugenol with dimethylsulfate produces methyl eugenol (4allyl-1,2-dimethoxybenzene) compound (2) with the yield of 98.8%. The bromination reaction of (2) produces 1-bromo-2-(2,3-dibromoprophyl)-4,5-dimethoxybenzene (3a), 1-bromo-4,5-dimethoxy-2(2,2,3-tribromopropyl)benzene (3b), and 4-(2,3-dibromopropyl)-1,2-dimethoxybenzene (3c) with the yield of 63%, 0.4%, and 10%, respectively. The dehydrobromination reaction of the compound (3a) with acrylic acid gives the compound (E)-3-(2-bromo-4,5-dimethoxyphenyl) allyl acrylate (4) with the yield of 38%. All product of the synthesis were purified by column chromatoghraphy and pure product were characterized by FTIR, 13C NMR, and 1H NMR. <p align="justify"> <br /> <br />