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Synthesis and Antibacterial Activity of 1,3,5,7-Tetrahydroxy-9,10-Anthraquinone and Anthrone Derivatives

VALENSI · Vol. ume No. 2 (2022) · hlm. 221–231

DOI
10.15408/jkv.v8i2.25279
ISSN
2548-3013, 2460-6065
Terbit
2022-11-25
Penerbit
Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University
Bahasa
eng

Abstrak

In this research, the synthesis of 1,3,5,7-tetrahydroxy-9,10-anthraquinone (1) and two anthrone derivatives, 1,3,5,7-tetrahydroxy-10H-anthracene-9-one (2) and 1-hydroxy-3,5,7,9-tetramethoxyanthracene (3) has been done. Compound 1 was synthesized by a symmetrical condensation reaction of 3,5-dihydroxybenzoic acid in concentrated sulfuric acid. Reduction of the carbonyl group in compound 1 with SnCl2/HCl-HOAc affords compound 2. Compound 3 was prepared by modifying the hydroxy groups of compound 2 by a methylation reaction. The synthesized compounds were identified using nuclear magnetic resonance spectroscopy (NMR) and a high-resolution mass spectrometry (HR-ESI-MS). The antibacterial activity test of the synthesized compounds against four pathogenic bacteria, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi, was carried out using the microdilution method. Compound 3 showed moderate activity against B. subtilis, E. coli and S. typhi with a MIC value of 37.5 µg/mL. Moderate activity was also shown by compound 2 against S. aureus, while compound 1 showed weak activity with a MIC value of 75 µg/mL against the four test bacteria.

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  • Bandung Institute of Technology
  • Syarif Hidayatullah State Islamic University Jakarta
  • University of Indonesia
  • Universitas Bhayangkara Jakarta Raya
  • Universitas Mathla'ul Anwar Banten
  • Padjadjaran University
  • Chulalongkorn University
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Rekan penulisOrganisasiArtikel bersama
Isalmi AzizSyarif Hidayatullah State Islamic University Jakarta11
Lia Dewi JuliawatyBandung Institute of Technology5
Nanda SaridewiSyarif Hidayatullah State Islamic University Jakarta5
Adawiah AdawiahSyarif Hidayatullah State Islamic University Jakarta4
Agustino ZulysUniversity of Indonesia4
Lisa AdhaniUniversitas Bhayangkara Jakarta Raya4
Elvira HermawatiBandung Institute of Technology4
Tarso RudianaUniversitas Mathla'ul Anwar Banten3
Eri BachtiarPadjadjaran University2
Dede SukandarSyarif Hidayatullah State Islamic University Jakarta2
Latifah TulhusnaSyarif Hidayatullah State Islamic University Jakarta2
Robby RoswandaBandung Institute of Technology2
Ade DanovaBandung Institute of Technology2
Warinthorn ChavasiriChulalongkorn University2
Anita AlniBandung Institute of Technology2
Euis Holisotan HakimBandung Institute of Technology2
Badrul UlumSyarif Hidayatullah State Islamic University Jakarta2
Adid Adep DwiatmokoNational Research and Innovation Agency2
Yulyani Nur AzizahSyarif Hidayatullah State Islamic University Jakarta2
Selviana RustantiSyarif Hidayatullah State Islamic University Jakarta1
Uly Fitria BaleSyarif Hidayatullah State Islamic University Jakarta1
Rizka FadhillaSyarif Hidayatullah State Islamic University Jakarta1
Fitri Nur RamadhanSyarif Hidayatullah State Islamic University Jakarta1
Muhamad Abdulkadir MartoprawiroBandung Institute of Technology1
Suci Zulaikha HildayaniBandung Institute of Technology1
Alfhons Daniel SirampunBandung Institute of Technology1
Rino R. MuktiBandung Institute of Technology1
Farhah Syahidatul MalaSyarif Hidayatullah State Islamic University Jakarta1
Reza AditamaBandung Institute of Technology1
Azzania FibrianiBandung Institute of Technology1
Ernawati Arifin Giri-RachmanBandung Institute of Technology1
Nathanael StevenBandung Institute of Technology1
Almira AlifiaBandung Institute of Technology1
Mellysa RahmitaBandung Institute of Technology1
Fera KurniadewiState University of Jakarta1
Iqbal MusthapaIndonesia University of Education1
Sri KomalaSyarif Hidayatullah State Islamic University Jakarta1

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Sumber metadata: OAI-PMH (metadata jurnal) http://journal.uinjkt.ac.id/index.php/valensi/oai, pertama di-harvest 10 Nov 2026, terakhir terlihat 10 Nov 2026.
Metadata asli (oai_dc) 
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	<dc:title xml:lang="en">Synthesis and Antibacterial Activity of 1,3,5,7-Tetrahydroxy-9,10-Anthraquinone and Anthrone Derivatives</dc:title>
	<dc:creator xml:lang="en">Nurbayti, Siti</dc:creator>
	<dc:creator xml:lang="en">Mujahidin, Didin</dc:creator>
	<dc:creator xml:lang="en">Syah, Yana Maolana</dc:creator>
	<dc:subject xml:lang="en">Anthraquinone</dc:subject>
	<dc:subject xml:lang="en">anthrone</dc:subject>
	<dc:subject xml:lang="en">antibacterial</dc:subject>
	<dc:subject xml:lang="en">methylation</dc:subject>
	<dc:subject xml:lang="en">reduction</dc:subject>
	<dc:description xml:lang="en">In this research, the synthesis of 1,3,5,7-tetrahydroxy-9,10-anthraquinone (1) and two anthrone derivatives, 1,3,5,7-tetrahydroxy-10H-anthracene-9-one (2) and 1-hydroxy-3,5,7,9-tetramethoxyanthracene (3) has been done. Compound 1 was synthesized by a symmetrical condensation reaction of 3,5-dihydroxybenzoic acid in concentrated sulfuric acid. Reduction of the carbonyl group in compound 1 with SnCl2/HCl-HOAc affords compound 2. Compound 3 was prepared by modifying the hydroxy groups of compound 2 by a methylation reaction. The synthesized compounds were identified using nuclear magnetic resonance spectroscopy (NMR) and a high-resolution mass spectrometry (HR-ESI-MS). The antibacterial activity test of the synthesized compounds against four pathogenic bacteria, Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Salmonella typhi, was carried out using the microdilution method. Compound 3 showed moderate activity against B. subtilis, E. coli and S. typhi with a MIC value of 37.5 µg/mL. Moderate activity was also shown by compound 2 against S. aureus, while compound 1 showed weak activity with a MIC value of 75 µg/mL against the four test bacteria.</dc:description>
	<dc:publisher xml:lang="en">Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University</dc:publisher>
	<dc:date>2022-11-25</dc:date>
	<dc:type>info:eu-repo/semantics/article</dc:type>
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	<dc:format>application/pdf</dc:format>
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	<dc:format>application/pdf</dc:format>
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	<dc:format>application/pdf</dc:format>
	<dc:identifier>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279</dc:identifier>
	<dc:identifier>10.15408/jkv.v8i2.25279</dc:identifier>
	<dc:source xml:lang="en">Jurnal Kimia Valensi; Jurnal Kimia VALENSI Volume 8, No. 2, November 2022; 221-231</dc:source>
	<dc:source>2548-3013</dc:source>
	<dc:source>2460-6065</dc:source>
	<dc:language>eng</dc:language>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/pdf</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/16997</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/16998</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/16999</dc:relation>
	<dc:relation>https://journal.uinjkt.ac.id/index.php/valensi/article/view/25279/17000</dc:relation>
	<dc:rights xml:lang="en">Copyright (c) 2022 Siti Nurbayti, Didin Mujahidin, Yana Maolana Syah</dc:rights>
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