ISOLATION OF BAECKEOL FROM BAECKEA FRUTESCENS (MYRTACEAE) LEAVES AND ITS FUNCTIONAL GROUP TRANSFORMATIONS AS A LEARNING MODEL TO ENHANCE UNDERSTANDING OF ORGANIC CHEMISTRY IN HIGH SCHOOL LEVEL

• Main Author: ROSMIATI (NIM: 90514013) , TATI
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/31237
• Institution: Institut Teknologi Bandung

<p align="justify">Baeckeol (1) is the main compound obtained from the leaves of medicinal plant Baeckea frustecens (Jung Rahab). In Indonesia, this plant spreads from South Sumatra, West Kalimantan, Sulawesi, Maluku and Irian Jaya. The part of this medicinal plant used in traditional medicine is leaves. Jung Rahab’s leaves can be used as treatment for fever, an abdominal pain, a diuretic and a mosquito repellent and a refreshing drink. Jung Rahab has an aromatic odor because it contains essential oils. According to previous research, it was reported that the methanol extract and baeckeol (1) have been examined for their cytotoxic activities against murine leukemia P-388 cells with IC50 values 19.6 &#61549;g/mL (active) and 10.9 &#61549;g/mL (not active), respectively. In order to increase the biological activity of baeckeol (1) therefore the study of various transformation of functional groups on baeckeol (1) has been conducted including benzylation, allylation, and prenylation of the hydroxy group and also the reduction of ketone group. In this research, baeckeol (1) has been isolated from methanol extract of Baeckea frustecens leaves (collected from Bangka island) by using vacuum liquid chromatography and recrystallization. Furthermore, baeckeol (1) analog compounds have been synthesized. Based on the literature, all compounds obtained from transformation are new compounds, namely baeckeol-1-O-benzil eter (15) as the benzylation product (99,0% yield), baeckeol-1-O-alil eter (16) as allylation product (98,3 % yield), baeckeol-1-O-prenil eter (17) as prenylation product (64,0% yield) and 2-(1-hydroxy-2-methylpropyl)-3,5-dimethoxy-6-methylphenol (18) was the reduction product (45,6% yield). Structure baeckeol (1) and the four compounds were characterized based on spectroscopic data, including 1D-NMR (1H, 13C), 2D-NMR (HSQC, HMBC), HR-ESIMS, IR, and UV-Vis. Moreover, the study of the transformation of functional groups on baeckeol (1) could become a model to enhance students understanding of learning organic chemistry in high school level. <p align="justify">