Hernawan Hernawan(1*), Bambang Purwono(2), Tutik Dwi Wahyuningsih(3)

(1) Technical Implementation Unit for Development of Chemical Engineering Processes, Indonesian Institute of Sciences, Gading, Playen, Gunungkidul, Yogyakarta 55861
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(*) Corresponding Author


Synthesis and antioxidant activity of 2-methoxy-4,6-di(prop-1-enyl) phenol from eugenol have been investigated. Synthesis was conducted through three stages of reaction. The first step was CTAB micellar catalytic O-allylation reaction at room temperature, to give 4-allyl-1-(allyloxy)-2-methoxybenzene (2). Compound (2) was subsequently heated for Claisen rearrangement and produced 2,4-diallyl-6- methoxyphenol (3). The final steps was isomerization of compound (3) in alkaline conditions in ethylene glycol, to yield 2-methoxy-4,6-di(prop-1-enyl) phenol (4). Antioxidant activity test was conducted by TBARS and DPPH methods. TBARS test showed that the compound (4) at a concentration of 50 μM could inhibit the oxidation of linoleic acid shown by the increasing of time lag phase (96 ± 2.94 min), reducing the rate of propagation (± 54.54%) and reducing of malonal dialdehyde (MDA) formation (68.04 ± 0.84%). The DPPH test revealed that compound (4) indicated DPPH free radical scavenging activity with IC50 107.66 μM and comparable with IC50 for BHT 107.37 μM.


Claisen rearrangement; DPPH; eugenol; isomerization; O-allylation

Full Text:

Full Text PDF


[1] Mastelić, J., Jerković, I., Blažević, I., Poljak-Blaži, M., Borović, S., Ivančić-Baće, I., Smrecki, V., Žarković, N., Brčić-Kostić, K., Vikić-Topić, D., and Muller, N., 2008, J. Agric. Food Chem., 56, 11, 3989–3996.

[2] Laguerre, M., Lecomte, J., and Villeneuve, P., 2007, Prog. Lipid Res., 46, 5, 244–282.

[3] Shireqi, I., Reddy, P., and Brenner, D.E., 2000, Crit. Rev. Oncol. Hematol., 33, 3, 157–167.

[4] Hernawan, 2007, Indo. J. Chem. 8, 1, 111–113.

[5] Roginsky, V., 2003, Arch. Biochem. Biophys., 414, 2, 261–270.

[6] Awasthi, P.K., Dixit, S.C., Dixit, N., and Sinha, A.K., 2008, J. Pharm. Res., 1, 2, 215–220

[7] Nur’aini, Purwono, B., and Tahir, I., 2007, Indo. J. Chem., 7, 1, 61–66.

[8] Hidalgo, M.E, De La Rosa, C., Carrasco, H., Cardona, W., Gallardo, C., and Espinoza, L., 2009, Quim. Nova, 32, 6, 1467–1470.

[9] Tominaga, H., Kobayashi, Y., Goto, T., Kasemura, K., and Nomura, M., 2005, Yakugaku Zasshi, 125, 4, 371–375.

[10] Esterbauer, H., Striegl, G., Puhl, H., and Rotheneder, M., 1989, Free Radical Res., 6, 1, 67–75.

[11] Yang, H., Dong, Y., Du, H., Shi, H., Peng, Y., and Li, X., 2011, Molecules, 16, 4, 3444–3455.

[12] Kamm, O., and Marvel, C.S., 1941, Org. Synth., 1, 25.

[13] Coombes, C.L., and Moody, C.J., 2008, J. Org. Chem., 73, 17, 6758–6762.

[14] Kadarohman, A., Sastrohamidjojo, H, and Muchalal, M., 1999, Study of the Complex Reaction Pathway of Eugenol Isomerization, Proceeding of 6th National Seminar on Organic Chemistry, Department of Chemistry, Universitas Gadjah Mada, 24-25 September 1999.

[15] Brigati, G., Lucarini, M., Mugnaini, V., and Pedulli, G.F., 2002, J. Org. Chem., 67, 4828-4832.

[16] Snelgrove, D.W., Lusztyk, J., Banks, J.T., Mulder, P., and Ingold, K.U., 2001, J. Am. Chem. Soc., 123, 469–477.


Article Metrics

Abstract views : 2472 | views : 2539

Copyright (c) 2012 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.

Analytics View The Statistics of Indones. J. Chem.