ISOLATION OF PHENOLIC COMPOUND FROM TEPHROSIA VOGELII AND THEIR TRANSFORMATION WITH SELECTFLUORTM

• Main Author: YULVIA, ANA
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/63787
• Institution: Institut Teknologi Bandung

This study aims to isolate secondary metabolites of Tephrosia vogelii and the transformation of isolated compounds using SelectfluorTM reagent. Previous research has shown that the seed extract of Tephrosia vogelii contains phenolic derivatives of the flavanone and rotenoid groups. SelectfluorTM or 1-chloromethyl- 4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis[tetrafluoroborate] is the source of F+ used for electrophilic fluorination reactions. The isolation methods used in this study include extraction, fractionation, separation, and purification using various chromatographic techniques. The structure of the isolate compound was determined based on 1D and 2D NMR. Five phenolic compounds have been isolated and identified from the seeds of Tephrosia vogelii, namely three flavanone derivatives [Isoloncocarpine (1), 7-methoxy-8-prenylflavanone (2), Pongacin (3)] and two rotenoid derivative compounds [Tefrosin (4) and Deguelin (5)]. Furthermore, the five isolated compounds were transformed using 0.5 equivalents of SelectfluorTM in acetonitrile solvent at 100 oC for 3 hours. TLC analysis of the reaction showed that only compounds 2, 4, and 5 showed the reaction product, namely 2,3-difluoro-7-methoxy-8-prenylflavanone (2.1), Dehydrotephrosine (4.1), 5'- demethyltephrosine (4.2), and 5'-demethyldeguelin (5.1). The reaction products of compound 4.1 are dehydration products of compound 4, while compounds 4.2 and 5.1 are products of hydrolysis of methoxy groups (-OCH3) into free -OH. The three reaction products, namely 4.1, 4.2, and 5.1, are new reaction products from SelectfluorTM reagent as a catalyst in tertiary alcohol dehydration and hydrolysis of methoxy (-OCH3) in aromatic groups. In conclusion, in this research, five phenolic derivative compounds have been isolated and the discovery of new chemical properties in SelectfluorTM reagent as a catalyst in the dehydration reaction and hydrolysis of the –OCH3 group.