Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation
<p class="Abstract"><span lang="EN-US">Dehydrozingerone (DHZ), 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, a natural compound found in the rhizome of ginger plants (<em>Zingiber officinale</em>), exhibits a wide range of bioactivities, including antioxida...
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Universitas Sultan Ageng Tirtayasa
2024-01-01
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| Series: | EduChemia |
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| Online Access: | https://jurnal.untirta.ac.id/index.php/EduChemia/article/view/24414 |
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| author | Annisa Mustika Pertiwi Deana Wahyuningrum |
| author_facet | Annisa Mustika Pertiwi Deana Wahyuningrum |
| author_sort | Annisa Mustika Pertiwi |
| collection | DOAJ |
| description | <p class="Abstract"><span lang="EN-US">Dehydrozingerone (DHZ), 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, a natural compound found in the rhizome of ginger plants (<em>Zingiber officinale</em>), exhibits a wide range of bioactivities, including antioxidant, anticancer, antimalarial, antidepressant, antifungal, and many other bioactivities. Conventionally, DHZ is synthesized through a cross-aldol Claisen-Schmidt condensation of vanillin and acetone, but this process often requires extended reaction times (up to 48 hours), results in low yields, and involves the excess use of organic solvents for purification. To address these limitations, this study aims to develop a green synthesis method for DHZ utilizing a 1-decyl-3-methylimidazolium bromide ([DMIM]Br) ionic liquid medium and microwave-assisted organic synthesis (MAOS) method. The experimental procedure involved optimizing the reaction conditions and varying the concentration of [DMIM]Br under microwave irradiation. Product characterization was performed by melting point determination, thin-layer chromatography (TLC), Fourier transform infrared (FTIR), and nuclear magnetic resonance (NMR) <sup>1</sup>H (500 MHz, CDCl<sub>3</sub>) and <sup>13</sup>C (125 MHz, CDCl<sub>3</sub>) spectroscopy. These findings indicate that the use of the [DMIM]Br ionic liquid significantly improved the purity and yield of DHZ products. The optimal conditions were synthesis from vanillin and acetone in a 1:10 molar ratio, 2.5 M NaOH, and 5% [DMIM]Br (w/v) using MAOS for 120 minutes (50°C, 300 W) to produce a 62.96% yield product in the form of a bright yellow solid with a melting point range of 129–130°C. The use of ionic liquids and MAOS provides a more efficient and environmentally friendly method for synthesizing DHZ, offering a significant reduction in reaction time and eliminating excess organic solvents, thus making it a promising alternative to traditional synthesis methods.</span></p> |
| format | Article |
| id | doaj-art-fadef9cda3ca4a9db485bc3b1c08326f |
| institution | Kabale University |
| issn | 2502-4779 2502-4787 |
| language | Indonesian |
| publishDate | 2024-01-01 |
| publisher | Universitas Sultan Ageng Tirtayasa |
| record_format | Article |
| series | EduChemia |
| spelling | doaj-art-fadef9cda3ca4a9db485bc3b1c08326f2024-11-10T07:38:27ZindUniversitas Sultan Ageng TirtayasaEduChemia2502-47792502-47872024-01-0191203210.30870/educhemia.v9i1.2441411802Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave IrradiationAnnisa Mustika Pertiwi0Deana Wahyuningrum1Master Program in Chemistry Teaching, Institut Teknologi Bandung, Bandung, IndonesiaInstitut Teknologi BandungDepartment of Chemistry, Institut Teknologi Bandung, Bandung, Indonesia<p class="Abstract"><span lang="EN-US">Dehydrozingerone (DHZ), 4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one, a natural compound found in the rhizome of ginger plants (<em>Zingiber officinale</em>), exhibits a wide range of bioactivities, including antioxidant, anticancer, antimalarial, antidepressant, antifungal, and many other bioactivities. Conventionally, DHZ is synthesized through a cross-aldol Claisen-Schmidt condensation of vanillin and acetone, but this process often requires extended reaction times (up to 48 hours), results in low yields, and involves the excess use of organic solvents for purification. To address these limitations, this study aims to develop a green synthesis method for DHZ utilizing a 1-decyl-3-methylimidazolium bromide ([DMIM]Br) ionic liquid medium and microwave-assisted organic synthesis (MAOS) method. The experimental procedure involved optimizing the reaction conditions and varying the concentration of [DMIM]Br under microwave irradiation. Product characterization was performed by melting point determination, thin-layer chromatography (TLC), Fourier transform infrared (FTIR), and nuclear magnetic resonance (NMR) <sup>1</sup>H (500 MHz, CDCl<sub>3</sub>) and <sup>13</sup>C (125 MHz, CDCl<sub>3</sub>) spectroscopy. These findings indicate that the use of the [DMIM]Br ionic liquid significantly improved the purity and yield of DHZ products. The optimal conditions were synthesis from vanillin and acetone in a 1:10 molar ratio, 2.5 M NaOH, and 5% [DMIM]Br (w/v) using MAOS for 120 minutes (50°C, 300 W) to produce a 62.96% yield product in the form of a bright yellow solid with a melting point range of 129–130°C. The use of ionic liquids and MAOS provides a more efficient and environmentally friendly method for synthesizing DHZ, offering a significant reduction in reaction time and eliminating excess organic solvents, thus making it a promising alternative to traditional synthesis methods.</span></p>https://jurnal.untirta.ac.id/index.php/EduChemia/article/view/24414dehydrozingerone (dhz), green chemistry, ionic liquid, microwave synthesis |
| spellingShingle | Annisa Mustika Pertiwi Deana Wahyuningrum Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation EduChemia dehydrozingerone (dhz), green chemistry, ionic liquid, microwave synthesis |
| title | Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation |
| title_full | Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation |
| title_fullStr | Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation |
| title_full_unstemmed | Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation |
| title_short | Green Synthesis of Dehydrozingerone (DHZ) Utilizing Ionic Liquid Medium and Microwave Irradiation |
| title_sort | green synthesis of dehydrozingerone dhz utilizing ionic liquid medium and microwave irradiation |
| topic | dehydrozingerone (dhz), green chemistry, ionic liquid, microwave synthesis |
| url | https://jurnal.untirta.ac.id/index.php/EduChemia/article/view/24414 |
| work_keys_str_mv | AT annisamustikapertiwi greensynthesisofdehydrozingeronedhzutilizingionicliquidmediumandmicrowaveirradiation AT deanawahyuningrum greensynthesisofdehydrozingeronedhzutilizingionicliquidmediumandmicrowaveirradiation |