SYNTHESIS OF 1,4-BIS [(1-HYDROXY-4-T-BUTYL-PHENYL) METHYL]PIPERAZINE AS ANTIOXIDANTS

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Susy Yunita Prabawati

Abstract


A study has been conducted to synthesize 1,4-bis [(1-hydroxy-4-t-butyl-phenyl)-methyl]piperazin using phenol derivate and investigate the capability of that compound, as an antioxidant. The synthesis was carried out through Mannich reaction using p-t-butylphenol, paraformaldehyde, and piperazine. The product was characterized by IR and 1H NMR spectroscopic. Testing of antioxidant activity was done with the immersion of DPPH (1,1-diphenyl-2 picrylhydrazyl) free radical method. The product was obtained as a white solid, with a point of 252,7-254,7 ºC and a yield of 65.76%. The test of antioxidant activity with DPPH method showed that 1,4-bis [(1-hydroxy-4-t-butyl-phenyl)-methyl]piperazin had the IC50 values was 0.84 nM. It means that the 1,4- bis[(1-hydroxy-4-t-butyl-phenyl )methyl]piperazine has potential as antioxidants.

Keywords


antioxidant, Mannich reaction, p-t-butylphenol, 1,4-bis[(1-hydroxy-4-t-butyl-phenyl)methyl]piperazin.

References


Aini, N., Purwono, B., Tahir, I. (2007). Structure–antioxidant activities relationship analysis of isoeugenol, eugenol, vanilin and their derivatives. Indonesian Journal of Chemistry, 7 (1), 61-66.

Apak R., Güçlü K., Demirata B., Özyürek M., Çelik S.E., Bektaşoğlu B., Berker K.I., dan Özyurt D. (2007). Comparative Evaluation of Various Total Antioxidant Capacity Assays Applied to Phenolic Compounds with the CUPRAC Assay. Molecules, 12, 1496-1547.

Chi K.W.,Yoon, S.A., Kwang, T.S., Hwang, H., dan Jeong, S.A. (2002). Synthesis of Diazacrown Ethers Containing Phenolic Side Arms and Their Complex with Divalent Metal Ions. Bulletin of the Korean Chemical Society, 23 (5).

Eryanti, Y., Zamri, A., Jasril, Rahmita. (2010). Sintesis Turunan 2-hidroksi Kalkon melalui Kondensasi Claisen-Schmidt dan Uji Aktivitasnya sebagai Antimikroba. Jurnal Natur Indonesia, 12, 2, 223-227.

Jun, M., Fu, H-Y., Hong, J., Wan, X., Yang, C.S., Ho, C-T. (2003). Comparison of Antioxidant Activities of Isoflavones from Kudzu Root (Pueraria lobate Ohwi). Journal of Food Science, 68 (6). 2117-2122.

Khalil, M.Y., Moustafa, A.A., dan Naguib, N.Y. (2007). Growth, Phenolic Compounds, and Antioxidant Activity of Some Medical Plants Grown under Organic Farming Condition. World Journal of Agricultural Sciences, 3(4): 451-457.

Klein, E., Lukeš, V., Cibulková, Z. (2005). On The Energetics Of Phenol Antioxidants Activity. Petroleum & Coal, 47 (1), 33-39, 2005.

Muthumani P., Neckmohammed, Meera R., Venkataraman S., Chidambaranathan N., Devi P., Kumar P.A.S. (2010). Synthesis and evaluation of anticonvulsant and antimicrobial activities of some Mannich bases of substituted aminophenol and acetophenone. International Journal Pharmaceutical and Biomedical Research, 1(3), 78-86.

Prabawati, S.Y., Setiawan, A., Fauzia, A. (2012). Sintesis Senyawa 1,4-bis [(2-hidroksi-3-metoksi-5-formaldehid-fenil)-metil] piperazin dari Bahan Dasar Vanilin dan Uji Aktivitasnya sebagai Zat Antioksidan. Kaunia, Vol. VIII, No.1, 30-43.

Prabawati, S.Y., Fauzia, A. (2015). Pemanfaatan Bahan Alami Eugenol sebagai Zat Antioksidan. Kaunia, Vol. XI, No.1, April, 11-18.

Prakash, D., Upadhyay, G.,Singh, B.N., Dhakarey, R., Kumar, S., dan Singh, K.K. (2007). Free Radical Scavenging Activities og Himalayan Rododendrons. Current Science, 92, 4, 526-532.

Salamah, N., Widyaningsih, W., Izzati, I., Susanti, H. (2015). Aktivitas Penangkap Radikal Bebas Ekstrak Etanol Ganggang Hijau Spirogyra sp. dan Ulva lactuca dengan Metode DPPH. Jurnal Ilmu Kefarmasian Indonesia, Vol.13, No.2, 145-150.

Shyamala, B.N., Naidu, M., Sulochanamma, G.S., Srinivas, P. (2007). Studies on the antioxidant activities of natural vanilla extract and its constituent compounds through in vitro models. Journal of Agricultural and Food Chemistry, 55, 7738–7743.

Sugianto NL. (2011). Pemberian jus delima merah (punica granatum) dapat meningkatkan kadar glutation peroksidase darah pada mencit (Mus musculus) dengan aktivitas fisik maksimal. Tesis. Denpasar: Program Pascasarjana Universitas Udayana, 3 & 5.

Suryawati, Frengki, Suardi, H.N. (2013). The Potential antioxidant activity of ethanolic extract of Aceh ant-plant (Mymercodia sp) on the free radical DPPH (1,1-Diphenyl-2-pikrylhidrazil). Proceedings of the 3th Annual International Conference Syiah Kuala, Oktober 2-4, Banda Aceh. Indonesia, 301-305.

Winarsi, H. (2007). Antioksidan Alami dan Radikal Bebas. Yogyakarta: Kanisius; 11-23.

Yu, L. (2008). Overview and Prospective, dalam Wheat Antioxidants, John Wiley & Sons, Inc., New Jersey.




DOI: http://dx.doi.org/10.20884/1.jm.2016.11.2.244

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Jurnal Ilmiah Kimia
Department of Chemistry, Faculty of Mathematics and Natural Sciences,
Universitas Jenderal Soedirman, Purwokerto, Indonesia

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