Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods

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...

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Autores principales:	Anita Alni, Didin Mujahidin, Shinta Ellisya Fauzia
Formato:	article
Lenguaje:	EN
Publicado:	University of Brawijaya 2019
Materias:	eugenol bromination eugenyl cinnamate photocatalysis epimers Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/8356ef3c86d64bc7bb05e74d060c5dd3
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spelling	oai:doaj.org-article:8356ef3c86d64bc7bb05e74d060c5dd32021-12-02T14:24:41ZSynthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods2302-46902302-4690https://doaj.org/article/8356ef3c86d64bc7bb05e74d060c5dd32019-06-01T00:00:00Zhttps://jpacr.ub.ac.id/index.php/jpacr/article/view/458/pdfhttps://doaj.org/toc/2302-4690https://doaj.org/toc/2302-4690Synthesis 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.Anita AlniDidin MujahidinShinta Ellisya FauziaUniversity of Brawijayaarticleeugenolbrominationeugenyl cinnamatephotocatalysisepimersChemistryQD1-999ENJournal of Pure and Applied Chemistry Research, Vol 8, Iss 2, Pp 140-146 (2019)
institution	DOAJ
collection	DOAJ
language	EN
topic	eugenol bromination eugenyl cinnamate photocatalysis epimers Chemistry QD1-999
spellingShingle	eugenol bromination eugenyl cinnamate photocatalysis epimers Chemistry QD1-999 Anita Alni Didin Mujahidin Shinta Ellisya Fauzia Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods
description	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.
format	article
author	Anita Alni Didin Mujahidin Shinta Ellisya Fauzia
author_facet	Anita Alni Didin Mujahidin Shinta Ellisya Fauzia
author_sort	Anita Alni
title	Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods
title_short	Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods
title_full	Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods
title_fullStr	Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods
title_full_unstemmed	Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods
title_sort	synthesis of eugenyl cinnamate from clove oil (syzygium aromaticum) via bromination-dehydrobromination methods
publisher	University of Brawijaya
publishDate	2019
url	https://doaj.org/article/8356ef3c86d64bc7bb05e74d060c5dd3
work_keys_str_mv	AT anitaalni synthesisofeugenylcinnamatefromcloveoilsyzygiumaromaticumviabrominationdehydrobrominationmethods AT didinmujahidin synthesisofeugenylcinnamatefromcloveoilsyzygiumaromaticumviabrominationdehydrobrominationmethods AT shintaellisyafauzia synthesisofeugenylcinnamatefromcloveoilsyzygiumaromaticumviabrominationdehydrobrominationmethods
_version_	1718391436609585152

Synthesis of Eugenyl Cinnamate from Clove Oil (Syzygium aromaticum) via Bromination-Dehydrobromination Methods

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