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Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products

Journal of Mathematical and Fundamental Sciences · Vol. 53 No. 1 (2021) · hlm. 86–96

DOI
10.5614/j.math.fund.sci.2021.53.1.6
ISSN
2338-5510, 2337-5760
Terbit
2021-06-07
Penerbit
Directorate for Research and Innovation (DRI) ITB
Bahasa
eng

Abstrak

The rhizome of Kaempferia galanga has been known to contain ethyl p-methoxycinnamate (EPMC) (1) as a main component, which has anti-inflammatory properties. Previously we have reported the structural modification of EPMC (1) to form another ester, nitrostyrene, and cinnammamide derivatives and then studied their structure-activity relationships as anti-inflammatory agent. In continuing our research, in this paper, we report the microwave-assisted Claisen-Schmidt condensation of EPMC (1) to synthesize a series of p-methoxystyryl ketones followed by a study of their anti-inflammatory activity. The reaction begins with microwave-assisted cleavage oxidation of hydrolyzed product of EPMC, p-methoxycinnamic acid (2) with Ca(NO3)2 for the synthesis of p-methoxybenzaldehyde (3). Furthermore, 3 was reacted with acetophenone, ethyl methyl ketone and acetone via microwave-assisted Claisen-Schmidt condensation for the synthesis of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (5a) (E)-1-(4-methoxyphenyl)pent-1-en-3-one (5b) and (E)-4-(4-methoxyphenyl)but-3-en-2-one (5c), respectively. The reaction products were characterized using spectroscopic techniques and were then tested for anti-inflammatory activity using in vitro anti-denaturation of protein assay. It was found that converting EPMC (1) to 5a and 5b reduced anti-inflammatory activity, while 5c retained anti-denaturation activity with an IC50 of 72.8 µg/ml.

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  • Syarif Hidayatullah State Islamic University Jakarta
  • Universitas Airlangga
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Rekan penulisOrganisasiArtikel bersama
Anggun Qurrota AiniUniversitas Airlangga2
Rosa AdelinaSyarif Hidayatullah State Islamic University Jakarta2
Dila Aulia MaharaniSyarif Hidayatullah State Islamic University Jakarta2
Muhammad Mirza HardiansyahSyarif Hidayatullah State Islamic University Jakarta2
Stevani SitorusSyarif Hidayatullah State Islamic University Jakarta2
Fitri Ratna DewiSyarif Hidayatullah State Islamic University Jakarta2
Laifa Annisa HendarminSyarif Hidayatullah State Islamic University Jakarta2
Mochamad Iqbal NurmansyahSyarif Hidayatullah State Islamic University Jakarta1
Suci Ahda NovitriSyarif Hidayatullah State Islamic University Jakarta1
Annisa Triana YusmanSyarif Hidayatullah State Islamic University Jakarta1
Estu Mahanani DhilasariSyarif Hidayatullah State Islamic University Jakarta1
Rurynta Ferly ShaviraSyarif Hidayatullah State Islamic University Jakarta1

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Sumber metadata: OAI-PMH (metadata jurnal) https://journals.itb.ac.id/index.php/jmfs/oai, pertama di-harvest 9 Nov 2026, terakhir terlihat 9 Nov 2026.
Metadata asli (oai_dc) 
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	<dc:title xml:lang="en-US">Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products</dc:title>
	<dc:creator>Komala, Ismiarni</dc:creator>
	<dc:creator>Supandi, Supandi</dc:creator>
	<dc:creator>Nurmeilis, Nurmeilis</dc:creator>
	<dc:creator>Yardi, Yardi</dc:creator>
	<dc:creator>Betha, Ofa Suzanti</dc:creator>
	<dc:creator>Indriyani, Nurkhyati Putri</dc:creator>
	<dc:creator>Moethia, Moethia</dc:creator>
	<dc:creator>Setiawan, Muhamad Beny</dc:creator>
	<dc:creator>Dharmawan, Ghilman</dc:creator>
	<dc:creator>Nufus, Putri Hayati</dc:creator>
	<dc:creator>Utami, Noni Tri</dc:creator>
	<dc:subject xml:lang="en-US">Claisen-Schmidt condensation</dc:subject>
	<dc:subject xml:lang="en-US">(E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one</dc:subject>
	<dc:subject xml:lang="en-US">(E)-1-(4-methoxyphenyl)pent-1-en-3-one</dc:subject>
	<dc:subject xml:lang="en-US">(E)-4-(4-methoxyphenyl)but-3-en-2-one</dc:subject>
	<dc:description xml:lang="en-US">The rhizome of Kaempferia galanga has been known to contain ethyl p-methoxycinnamate (EPMC) (1) as a main component, which has anti-inflammatory properties. Previously we have reported the structural modification of EPMC (1) to form another ester, nitrostyrene, and cinnammamide derivatives and then studied their structure-activity relationships as anti-inflammatory agent. In continuing our research, in this paper, we report the microwave-assisted Claisen-Schmidt condensation of EPMC (1) to synthesize a series of p-methoxystyryl ketones followed by a study of their anti-inflammatory activity. The reaction begins with microwave-assisted cleavage oxidation of hydrolyzed product of EPMC, p-methoxycinnamic acid (2) with Ca(NO3)2 for the synthesis of p-methoxybenzaldehyde (3). Furthermore, 3 was reacted with acetophenone, ethyl methyl ketone and acetone via microwave-assisted Claisen-Schmidt condensation for the synthesis of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (5a) (E)-1-(4-methoxyphenyl)pent-1-en-3-one (5b) and (E)-4-(4-methoxyphenyl)but-3-en-2-one (5c), respectively. The reaction products were characterized using spectroscopic techniques and were then tested for anti-inflammatory activity using in vitro anti-denaturation of protein assay. It was found that converting EPMC (1) to 5a and 5b reduced anti-inflammatory activity, while 5c retained anti-denaturation activity with an IC50 of 72.8 µg/ml.</dc:description>
	<dc:publisher xml:lang="en-US">Directorate for Research and Innovation (DRI) ITB</dc:publisher>
	<dc:date>2021-06-07</dc:date>
	<dc:type>info:eu-repo/semantics/article</dc:type>
	<dc:type>info:eu-repo/semantics/publishedVersion</dc:type>
	<dc:format>application/pdf</dc:format>
	<dc:identifier>https://journals.itb.ac.id/index.php/jmfs/article/view/13138</dc:identifier>
	<dc:identifier>10.5614/j.math.fund.sci.2021.53.1.6</dc:identifier>
	<dc:source xml:lang="en-US">Journal of Mathematical and Fundamental Sciences; Vol. 53 No. 1 (2021); 86-96</dc:source>
	<dc:source>2338-5510</dc:source>
	<dc:source>2337-5760</dc:source>
	<dc:source>10.5614/j.math.fund.sci.2021.53.1</dc:source>
	<dc:language>eng</dc:language>
	<dc:relation>https://journals.itb.ac.id/index.php/jmfs/article/view/13138/5234</dc:relation>
	<dc:rights xml:lang="en-US">Copyright (c) 2021 Journal of Mathematical and Fundamental Sciences</dc:rights>
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