STUDY OF EUGENOL TRANSFORMATION TOWARDS A SYNTHESIS OF PHENYL PROPANE MOIETY OF SILYMARIN

• Main Author: UMMAH (NIM : 20514052), KHOIROTUL
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/22827
• Institution: Institut Teknologi Bandung

Indonesia is one of the largest clove oil-producing countries in the world. The main component of clove oil is eugenol (80%) which has a basic structure of phenyl propane with the functional groups of allyl, phenol and ether. The phenyl propane unit can be used as building blocks for synthesis of the active ingredient of hepatitis drug silymarin. Hepatitis is an acute disease and becomes worldwide health issues, including Indonesia. With the availability of eugenol which is abundant in Indonesia, the transformation eugenol is very important to enhance its benefit and economic value. Therefore, this research aims to utilize eugenol from clove oil as a precursor for the synthesis of phenyl propane units of silymarin. Here, we report products from eugenol transformation on propane moety via oxidation using molecular oxygen under Wacker condition (a) and alpha hydroxylation of ketone catalized by iodine (b). The product was characterized by IR, NMR and mass spectroscopies. The yield of compound 1 is 45% and its formation is indicated by a present of the ketone signal at δC 206.9 ppm and absorption of ketone which appears at wavenumber 1708 cm-1 on the IR spectrum. That is also supported by mass spectrometry data which showed peaks at (M-H)- m/z 179.0707 which is molecular mass of compound 1. While the yield of compound 2 which has been obtained from the hydroxylation of α-carbonyl is 35%. The structure of compound 2 was identified by 1H-NMR and showed proton signals of α-hydroxy ketones and methine at δH 4.26 ppm and 5.02 ppm. Measurement of mass spectrometry of the compound 2 showed a molecular mass of (M-H)- m/z 195.0654. A selective protection of secunder alcohol group was achieved by TMS-protection (c) and obtained the yield of compound 3 is 43%. In the 1H-NMR spectrum of compound 3 showed proton signals of one unit of trimethyl silane (TMS) and proton signals of α-hydroxy ketones does not appear in the NMR spectrum. Furthermore, the selective protection of phenol group was applied by TBS-group (d) and obtained the yield of compound 4 is 52%. The compound 4 was confirmed by the proton signals of one unit of t-butyl dimethylsilane (TBS) coupled with the absence of phenol signals in 1H-NMR spectrum. By products of the reaction (a) is vanillin, while the byproducts of reaction (b) is vanillin, 1-(4-hydroxy-3-methoxyphenyl)-propan-1,2-dione and 1-(4-hydroxy-3-methoxy-phenyl)-1-iodo-propan-2-one. This product from the transformation of eugenol potents to be a part of dioxane moety of the sylimarin.