Jurnal Kimia Valensi, Vol 8(2), November 2022, 221-231 Available online at Website: http://journal.uinjkt.ac.id/index.php/valensi Copyright©2022, Published by Jurnal Kimia Valensi P-ISSN: 2460-6065, E-ISSN: 2548-3013 Synthesis and Antibacterial Activity of 1,3,5,7-Tetrahydroxy-9,10- Anthraquinone and Anthrone Derivatives Siti Nurbayti 1 , Didin Mujahidin 2 , Yana Maolana Shah 2 1 Department of Chemistry, Faculty of Science and Technology, UIN Syarif Hidayatullah Jakarta Jl. Ir. H. Juanda No. 95, Ciputat, South Tangerang 15412, Indonesia 2 Department of Chemistry, Faculty of Mathematics and Natural Science, Bandung Institute of Technology Jl. Ganesha No. 10, Bandung, 40132, Indonesia *Corresponding author: baytikimia@uinjkt.ac.id Received: March 2022; Revision: April 2022; Accepted: November 2022; Available online: November 2022 Abstract 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 SnCl 2 /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. Keywords: anthraquinone, anthrone, antibacterial, methylation, reduction. DOI: 10.15408/jkv.v8i2.25279 1. INTRODUCTION Anthraquinone is a polycyclic aromatic compound consisting of an anthracene ring with two ketone groups at positions C-9 and C-10. The reduction of one of the ketone groups in anthraquinone produces anthrone compound. Different types of anthraquinone have been successfully isolated from plants (Dave & Ledwani, 2012; Xu et al., 2014), fungi (Masi & Evidente, 2020), lichen (Manojlovic et al., 2010), and insects (Shamim et al., 2014). The variety and position of functional groups on the aromatic rings of anthraquinone and anthrone affect their biological activity. The results of research on anthraquinone and anthrone derivative compounds (Figure 1) show various biological activities, including anticancer (Ali et al., 2000; Li et al., 2020), antiviral (Barnard et al., 1992; Feilcke et al., 2019), antioxidant (Malterud et al., 1993; Zengin et al., 2016; Al- Tamimi et al., 2020) and antibacterial (Park et al., 2006; Hamed et al., 2015; Bunbamrung et al., 2018). As antibacterials, some anthraquinone-derived compounds (Figure 2) show a MIC (minimum inhibitory concentration) value of less than 10 μ g/mL (Chukwujekwu et al., 2006; Kuete et al., 2007). Therefore this group of compounds has the potential to be developed as antibiotic raw materials. The development of anthraquinone and anthrone as antibacterial compounds must be followed by anticipation of their provision, one of which is a provision by synthesis. The synthesis of anthraquinone derivatives is mainly carried out through the Friedel-Crafts reaction between phthalate anhydride and substituted benzene using catalysts such as AlCl 3 /H 2 SO 4 (Naeimi & Namdari, 2008) and KAl(SO 4 ) 2 .12H 2 O (Madje et al., 2010).