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All Journal The Journal of Pure and Applied Chemistry Research Journal of Mathematical and Fundamental Sciences
Anita Alni
Division Of Organic Chemistry, Faculty Of Mathematics And Natural Sciences, Institut Teknologi Bandung
Astronomy Chemical Engineering, Chemistry & Bioengineering Chemistry Earth & Planetary Sciences Materials Science & Nanotechnology Mathematics Medicine & Pharmacology Physics

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Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods Anita Alni; Didin Mujahidin; Shinta Ellisya Fauzia
The Journal of Pure and Applied Chemistry Research Vol 8, No 2 (2019): Edition May-August 2019
Publisher : Chemistry Department, The University of Brawijaya

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.21776/ub.jpacr.2019.008.02.458

Abstract

Synthesis of bioactive materials based on Indonesian natural products as precursors are potential to achieve a sustainable supply of modern medicines. Eugenyl cinnamate is a crucial building blocks in many bioactive compunds such as hepatoprotective silibinin. This research features simple synthesis of eugenyl cinnamate from eugenol, an essential oil presents as major constituent of clove oil (Syzygium aromaticum). The transformations were carried out via protection of hydroxyl group, bromination, and dehydrobromination reactions of eugenol (1) consecutively. The products of the synthesis were purified by gravity column chromatography and were characterized by FTIR and NMR spectroscopy. Benzylation of eugenol was carried out under basic condition with high yield (94.3%). Characterization by spectroscopic methods showed that eugenyl benzyl ether (2) was formed. Bromination of eugenyl benzyl ether yielded three products, namely: dibromo (3a and 3b), and tri-bromo eugenyl benzyl ether (3c). Compound 3a and 3b were epimers based on intensive NMR analysis (1H, 13C and DEPT). These epimers were separable using simple gravitational colomn chromatography. Bromination of eugenyl acetyl ether (4) yielded the targeted dibromo product (5). Dehydrobromination reaction of compound 5 with cinnamic acid yielded the eugenyl cinnamate (6) with yield of 23.2%. This compound is precursor in the hetero Diels-Alder reaction to form the dioxan unit of Silibinin. 
Unexpected Dimer from Demethylization Reaction of Eugenol under Acidic Conditions Anita Alni; Meilisa Dara Puspita; Didin Mujahidin
Journal of Mathematical and Fundamental Sciences Vol. 51 No. 1 (2019)
Publisher : Institute for Research and Community Services (LPPM) ITB

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.5614/j.math.fund.sci.2019.51.1.5

Abstract

Eugenol is an alkenyl phenol compound obtained as an essential oil from different parts of the clove such as its leaves and flowers. The essential oil from cloves can contain up to 90% eugenol, which is mainly responsible for its aroma. Eugenol is an interesting compound due to its simplicity and richness in functionalities, making it a valuable building block in synthesis. One of the key steps in eugenol transformation is demethylation to produce a hydroxycavicol. Demethylation is commonly carried out using a nucleophilic or an acidic method. In this study, a simple yet reliable nucleophilic method for demethylation using lithium chloride (LiCl) was attempted. The product was characterized by NMR, FTIR and HRMS spectroscopy. The absence of a methoxy signal at 3.5-4 ppm in the 1H NMR spectrum suggests that demethylation was successful. The HRMS result showed m/z 149.0596, confirming the formation of product. The demethylation reaction under acidic conditions formed a dimer of eugenol with the methoxy group still intact. This was supported by the 1H NMR data, which showed methoxy signals at 3.85 and 3.82 ppm and integration in the aromatic region, which suggests a dimer structure. 
Co-Authors Didin Mujahidin Didin Mujahidin Lasmaryna Sirumapea M. Bachri Amran Meilisa Dara Puspita Muhammad Ali Zulfikar Shinta Ellisya Fauzia