Potassium Permanganate-Catalyzed Alpha-Pinene Oxidation: Formation of Coordination Compound with Zinc(II) and Copper(II), and Growth Inhibition Activity on Staphylococcus aureus and Escherichia coli

https://doi.org/10.22146/ijc.21178

Masruri Masruri(1*), Rekfa Wika Amini(2), Mohammad Farid Rahman(3)

(1) Department of Chemistry, University of Brawijaya, Jl. Veteran Malang 65145, East Java
(2) Department of Chemistry, University of Brawijaya, Jl. Veteran Malang 65145, East Java
(3) Department of Chemistry, University of Brawijaya, Jl. Veteran Malang 65145, East Java
(*) Corresponding Author

Abstract


Catalytic oxidation of alpha-pinene was investigated using potassium permanganate as an oxidant. The reaction consumed catalyst following stoichiometric amount instead of the catalytic one. The keto-carboxylate compound 2 was afforded as the oxidation product. Further study of its complex compound with copper(II) and zinc(II) was also reported including their activity for inhibiting the growth of Staphylococcus aureus and Escherichia coli. In overall, the complex compound shows important result by inhibiting the bacterial growth.

Keywords


alpha-pinene; catalytic oxidation; antibacterial; natural product

Full Text:

Full Text PDF


References

[1] Amini, R.W., Masruri, and Rahman, M.F., 2014, Jurnal Ilmu Kimia Universitas Brawijaya, 1 (1), 147–153.

[2] Masruri, Rahman, M.F., and Prasodjo, T.I., 2007, Jurnal Ilmu-Ilmu Hayati (Life Sciences), 19 (1), 32–35.

[3] Rodrigues-Corrêa, K.C.S., de Lima, J.C., and Fett-Neto, A.G., 2012, Food Energy Secur., 1 (2), 81–93.

[4] Pinheiro, M.A., Magalhães, R.M., Torres, D.M., Cavalcante, R.C., Mota, F.S.X., Coelho, E.M.A.O., Moreira, H.P., Lima, G.C., Araújo, P.C.C., Cardoso, J.H.L., de Souza, A.N.C., and Diniz, L.C.L., 2015, Pharmacogn. Mag., 11 (41), 123–130.

[5] Bocci, F., and Frega, N., 1996, J Am. Oil Chem. Soc., 73 (6), 713–716.

[6] Vardar-Unlü, G., Candan, F., Sökmen, A., Daferera, D., Polissiou, M., Sökmen, M., Dönmez, E., and Tepe, B., 2003, J. Agric. Food Chem., 51 (1), 63–67.

[7] Husnul Khotimah, Diana Lyrawati, and Masruri, 2006, Antiinflammatory effects of alpha-pinene extracted from Pinus mercusii on levels of TNFa signalling, iNOS, and apoptosis of neuronal cells, Proceeding Asian Symposium on Medicinal Plants and Others (ASOMP 2006), Padang.

[8] Masruri, and Srihardyastuti, A., 2005, NATURAL J., 9 (1), 15–21.

[9] Clayden, J., Greeves, N., and Warren, S., 2012, Organic Chemistry, 2nd Ed., Oxford University Press, New York.

[10] Fisher, G.S., Goldblatt, L.A., and Stinson, J.S., 1951, Converting alpha-pinene to mixtures of acids, U.S. Patent 2,750,411

[11] Zhang, X., Chen, Z., Wang, H., He, S., and Huang, D., 2009, Atmos. Environ., 43 (29), 4465–4471.

[12] Holloway, F., Anderson, H.J., and Rodin, W., 1955, Ind. Eng. Chem., 47 (10), 2111–2113.

[13] Liu, S.T., Reddy, K.V., and Lai, R.Y., 2007, Tetrahedron, 63 (8), 1821–1825.

[14] Carlsen, P.H.J., Katsuki, T., Martin, V.S., and Sharpless, K.B., 1981, J. Org. Chem., 46 (19), 3936–3938.

[15] Moglioni, A.G., García-Expósito, E., Aguado, G.P., Parella, T., Branchadell, V., Moltrasio, G.Y., and Ortuño, R.M., 2000, J. Org. Chem., 65 (13), 3934–3940.

[16] Ziyat, H., Ali, M.A., Karim, A., Meliet, C., Castanet, Y., and Mortreux, A., 2004, Acta Chim. Slov., 51, 223–230.

[17] Padala, K., and Jeganmohan, M., 2012, Org. Lett., 14 (4), 1134–1137.

[18] Tan, X., Liu, B., Li, X., Li, B., Xu, S., Song, H., and Wang, B., 2012, J. Am. Chem. Soc., 134 (39), 16163–16166.

[19] Liu, Y., Song, R.J., Wu, C.Y., Gong, L.B., Hu, M., Wang, Z.Q., Xie, Y.X., and Li, J.H., 2012, Adv. Synth. Catal., 354 (2-3), 347–353.

[20] Rubinstein, A., Jiménez-Lozanao, P., Carbó, J.J., Poblet, J.M., and Neumann, R., 2014, J. Am. Chem. Soc., 136 (31), 10941–10948.

[21] Tercio, J., Ferreira, B., Cruz, W.O., Vieira, P.C., and Yonashiro, M., 1987, J. Org. Chem., 52 (16), 3698–3699.

[22] Verma, P.N., Sheikh, J.I., and Juneja, H.D., 2011, World Appl. Sci. J., 14 (8), 1154–1157.

[23] Aziz, A.A.A., Salem, A.N.M., Sayed, M.A., and Aboaly, M.M., 2012, J. Mol. Struct., 1010, 130–138.

[24] Konde, K.J., Patil, V.R., and Malve, S.P., 2004, Acta Pol. Pharm., 61 (2), 123–125.

[25] Kuwar, A.S., Shimpi, S.R., Mahulikar, P.P., and Bendre, R.S., 2006, J. Sci. Ind. Res., 65 (8), 665–669.

[26] Subhasish, S., Dharumadurai, D., Sarvanan, C., and Annamalai, P., 2009, FU Phys. Chem. Technol., 7 (1), 73–80.

[27] Chang, E.L., Simmers, C., and Knight, D.A., 2010, Pharmaceutical, 3, 1711–1728.



DOI: https://doi.org/10.22146/ijc.21178

Article Metrics

Abstract views : 7219 | views : 8676


Copyright (c) 2016 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 

Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web Analytics View The Statistics of Indones. J. Chem.