Assisted ultrasonic wave of vanillin derivatives synthesis and antioxidant activity using DPPH method
Article Sidebar
Main Article Content
Abstract
In recent years, the need for compounds with antioxidant activities have expanded. Generally, the natures of these compounds involve the presence of conjugated double bonds, phenolic groups, and resonance effects on the structure. One of the compounds with the phenolic group is vanillin. It can be modified into the derivative of 1,8-dioxo-octahydroxantene compound due to its aldehyde content. Meanwhile, 1,8-dioxo-octahydroxantene compound has two 2- cyclohexenone rings bound in the pyran ring and one phenolic group, expected to carry more excellent antioxidant activity than vanillin. The 9-(4-hydroxy-3-methoxyphenyl)-3,4,5,6,7,9- hexahydro -1H-xantene-1,8(2H)-dione (Compound 1) was synthesized from 1,3- cyclohexanedione and vanillin through Knoevenagel's condensation reaction aided with an acid catalyst with a single reaction phase. Besides, green chemistry was adopted in this study using environmentally friendly catalysts from lime juice and ultrasonic wave. The synthesized compounds' structure was confirmed through the spectrophotometer IR, GC-MS, and 1H-NMR spectrometer, while its antioxidant activity was tested using the DPPH method. The reaction occurred with and without lime juice catalyst, producing yields of 6.65% and 70.58%, respectively. The results of the antioxidant activity test suggest that Compound 1 carries substantially robust antioxidant activities, with IC50 of 0.99 ppm.
Downloads
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
Copyright
Open Access authors retain the copyrights of their papers, and all open access articles are distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution and reproduction in any medium, provided that the original work is properly cited.
The use of general descriptive names, trade names, trademarks, and so forth in this publication, even if not specifically identified, does not imply that these names are not protected by the relevant laws and regulations.
While the advice and information in this journal are believed to be true and accurate on the date of its going to press, neither the authors, the editors, nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein.
This work is licensed under a Creative Commons Attribution 4.0 International License.
References
2. D. K. Pratami, T. Indrawati, I. Istikomah, S. Farida, P. Pujianto, M. Sahlan. Antifungal activity of microcapsule propolis from Tetragonula spp. to Candida albicans. Commun. Sci. Technol. 5 (2020) 16-21.
3. V. Lobo, A. Patil, A. Phatak, N. Chandra, Free radicals, antioxidants and functional foods: Impact on human health, Pharmacogn Rev. 4-8 (2010) 118–26.
4. J. Lü, P. Lin, Q. Yao, C. Chen, Chemical and molecular mechanisms of antioxidants: Experimental approaches and model systems, J Cell Mol Med. 14-4 (2010) 840–60.
5. S. Prabawati, A. Wijayanto, Synthesis of 1,4-Bis [(1-Hydroxy-4-T-Butyl-Phenyl) Methyl]Piperazine As Antioxidants, Molekul. 11-2 (2016) 220-229.
6. S. Zukic, E. Veljovic, S. Spirtovi?-Halilovic, S. Muratovic, A. Osmanovic, S. Trifunovic, et al., Antioxidant, antimicrobial and antiproliferative activities of synthesized 2,2,5,5-tetramethyl-9-aryl-3,4,5,6,7,9-hexahydro-1h-xanthene-1,8(2h )-dione derivatives, Croat Chem Acta 91-1 (2018) 1–9.
7. R. Retnosari, A. Lestari, A. Santoso, D. Sukarianingsih, Y. Rosidah, Synthesis of 9-(4-bromophenyl)-3,4,5,6,7,9-hexahydro-1 H-xanthene-1,8(2 H)-dione using lime and lemon juice as a green catalyst and its antioxidant activity, AIP Conf. Proc. 2353 (2021) 030036-1-8
8. A. Napoleon, F. Khan, Potential anti-tubercular and in vitro anti-inflammatory agents: 9-Substituted 1,8-dioxo-octahydroxanthenes through cascade/ domino reaction by citric fruit juices, Med Chem Res. 23-11 (2014) 4749–476060.
9. T. Khatab, A. El-Mekabaty, Z. Gamala, E. Kandil, An efficient catalytic synthesis of 1,8-dioxo-octahydroxanthene derivatives with anti-oxidant scanning, Egypt J Chem. 61-4 (2018) 661–666.
10. A. Pramanik, S. Bhar, Alumina-sulfuric acid catalyzed eco-friendly synthesis of xanthenediones, Catal Commun. 20 (2012) 17–24.
11. W. Dos Santos, L. Da Silva-Filho, Facile and efficient synthesis of xanthenedione derivatives promoted by niobium pentachloride, Chem Pap. 70-12 (2016) 1658–1664.
12. A. Ghatak, D. Sinha, M. Das, Experimental investigations on the green synthesis of xanthenediones catalysed by VOSO4 and computational studies, Chem Data Collect. 30 (2020) 2–8.
13. R. Retnosari, N. Puteri, S. Sutrisno, S. Marfu'ah, A. Santoso, D. Sukarianingsih, et al., Synthesis of 9-(4-hydroxyphenyl)-3,4,6,7-tetrahydro-2 H-xanthene-1,8(5 H,9 H)-dione using lime and lemon juice as an acidic catalyst and its antioxidant activity, AIP Conference Proceedings 2353 (2021) 030052-1-9
14. A. Dadhania, V. Patel, D. Raval, Catalyst-free sonochemical synthesis of 1,8-dioxo-octahydroxanthene derivatives in carboxy functionalized ionic liquid, Comptes Rendus Chim. 15-5 (2012) 378–383.
15. N. Mulakayala, G. Kumar, D. Rambabu, M. Aeluri, M. Rao, M. Pal, A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound, Tetrahedron Lett. 53-51 (2012) 6923–6926.
16. P. Iniyavan, S. Sarveswari, V. Vijayakumar, Synthesis and antioxidant studies of novel bi-, tri-, and tetrapodal 9-aryl-1,8-dioxo-octahydroxanthenes, Tetrahedron Lett. 56-11 (2015) 1401–1406.
17. J. Yu, L. Wang, J. Liu, F. Guo, Y. Liu, N. Jiao, Synthesis of tetraketones in water and under catalyst-free conditions, Green Chem. 12-2 (2010) 216–219.
18. V. Nour, I. Trandafir, M. Ionica, HPLC Organic Acid Analysis in Different Citrus Juices under Reversed Phase Conditions, Not. Bot. Hort. Agrobot. Cluj 38-1 (2010) 44-48.
19. G. Chatel, How Sonochemistry Contributes to Green Chemistry?, Ultrasonics Sonochemistry 40B (2018) 117-122.
20. Mahlinda, D. Supardan, H. Husin, M. Riza, In situ Transesterication of Screw Pine Seed (Pandanus tectorius) Tobiodiesel using Ultrasound, J Teknol Ind Pertan.26-3 (2016) 294–300.
21. S. Sancheti, P. Gogate, A review of engineering aspects of intensification of chemical synthesis using ultrasound, Ultrason Sonochem. 36 (2017) 527–543.
22. B. Banerjee, Recent developments on ultrasound assisted catalyst-free organic synthesis, Ultrason Sonochem. 35 (2017) 1–14.
23. D. Candani, M. Ulfah, W. Noviana, Pemanfaatan Teknologi Sonikasi, FMIPA Universitas Negeri Padang 2-26 (2018) 1-12.
24. V. Desiyana, A. Haryanto, S. Hidayati, Pengaruh Rasio Molar Dan Waktu Reaksi Terhadap Hasil Dan Mutu Biodisel Melalui Reaksi Transesterifikasi Dengan Gelombang Ultrasonik, Jurnal Teknik Pertanian Lampung 3-1 (2014) 49–58.
25. T. Jin, N. Qi, M. Li, L. Han, L. Liu, T. Li, One-pot Synthesis of 9-Aryl-1,8-dioxo-1,2,3,4,6,7,8- octahydroxanthenes Catalyzed by p-Dodecylbenzene Sulfonic Acid in Aqueous Media, Asian Journal of Chemistry 19-5 (2007) 3803-3809
26. L. Nirwani, H. Ansory, A. Nilawati, Synthesis of 2 , 4-Dihydroxyacetophenone Compound and its Antioxidant Activity Assay, Jurnal Farmasi Indonesia 15-1 (2018) 65–70.