SYNTHESIS OF CONIFERYL ALCOHOL MOIETY AS PRECURSOR OF SYNTHESIS OF SYLIBIN BY USING EUGENOL

• Main Author: MARDLIYAH (NIM : 20514037), ANA
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/25468
• Institution: Institut Teknologi Bandung

<p align="justify">Indonesia is one of the largest producer country of clove in the world. The major compound of the clove essential oil is eugenol up to 89%. Eugenol has phenyl propane (C6-C3) basic skeleton with the allyl, phenol and methoxy moiety. The allyl moiety of eugenol can be transformed into another functional group which has better activity by several reaction so that it can be used as building block in organic synthesis. Based on retrosynthetic analysis, one of the various bioactive compound that may can be synthesis by using eugenol as precursor is sylibin. Sylibin is a natural product that has hepatoprotective activity and commonly used as herbal suplement for hepatitis patient. Whereas hepatitis is the world health problem including in Indonesia. Therefore this research is aim to get the transformation of eugenol that potentially as a precursor of coniferyl alcohol moiety for synthesis of sylibin.In this research the transformation of allyl moiety from eugenol into coniferyl alcohol 3 has been succeessfully trough bromide addition reaction followed by elimination reaction (dehydrobromination). The structure of synthesized products were identified by NMR, FTIR and MS spectroscopy data. OREugenolR=OH1R=OAcaOAcOBrOAcOAcOBrBrOAcOOO22a3bc+OOHOOOHOHOOHOHOMeSylibin(77%)(13%)(51%) Reagent: a. CH3COCl (2eq), refluks, 1 h. b. Br2 (1eq), CH3COOH, 10 oC, 1 h. c. benzoic acid (1,1eq), K2CO3 (2eq), DMSO, RT, 24 h.<p align="justify">