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

Masruri Masruri, Rekfa Wika Amini, Mohammad Farid Rahman


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.


alpha-pinene; catalytic oxidation; antibacterial; natural product

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

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

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

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.

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

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.

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.

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

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

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

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

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

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

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

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.

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

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

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

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.

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

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

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

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

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

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

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

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

DOI: http://dx.doi.org/10.22146/ijc.1044

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