SYNTHESIS STUDY OF MAIN UNIT ANTICHOLESTEROL STATIN COMPOUNDS THROUGH TRANSFORMATION OF 5,6-DEHIDROKAWAIN FROM ALPINIA MALACCENSIS

• Main Author: WAHYU NUR SARWENDAH, NILAM
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/23494
• Institution: Institut Teknologi Bandung

Statin has 3,5- dihydroxyheptanoat anti-collesterole compound as its main unit . This unit can be synthesized assimetrically by reduction of 3,5-dioxoheptanoat or 4-hydroxypyran-2-on unit. One of source that have 3–hydroxypyran-2-on is 5,6-dehydrokawain compound. It is major component in Alpinia malaccensis fruit extract, known as " lajah gowa ". In this study, the 5,6-dehydrokawain compound has been isolated from A. malaccensis fruit by extraction phase using acetone solvent followed by purification using chromatographic technique. Isolation process produce 5,6-dehidrokawain with a yield of up to 18 %. 5,6-dehydrokawain transformation using sodium methoxide is successfully open pyranone ring followed by degradation of 4 carbon atoms and produces cinnamic acid with a yield of 50%. While the 5,6-dehydrokawain hydrogenation reaction using hydrogen gas at low pressure with Pd/TiO2 catalyst successfully reduce internal double bond without damaging the pyranone ring and produce dihydro-5,6-dehydrokawain with a yield of 74 %. All the products were characterized using 1H-NMR and 13C-NMR. Harder condition is require for pyranone ring reduction in 5,6-dehydrokawain to produce 3,5-dihydroxy carboxylic as statin unit.