Pemanfaatan Minyak Daun Cengkeh untuk Sintesis 3,4-dimetoksibenzil Sianida sebagai Bahan Dasar Sintesis Isoflavon

Andi Hairil Alimuddin, Sabirin Matsjeh, Chairil Anwar, Mustofa Mustofa


This research was aimed to utilize eugenol isolated from clove leave oil in the synthesis of isoflavones. Eugenol was usedas a raw material by converting into 3,4-dimethoxybenzyl cyanide through several stages of reactions. These stages weremethylation of eugenol, isomerization of methyleugenol, oxydation of methylisoeugenol, reduction of 3,4-dimethoxybenzaldehyde, halogenation of 3,4-imethoxybenzyl alcohol and nitrilization of 3,4-dimethoxybenzyl chloride to3.4-dimethoxybenzyl cyanide. Methylation of eugenol using dimethylsulfate and NaOH catalyst produced methyleugenolin 93.60% purity. Isomerization of methyleugenol employing base of potassium tertiary butoxide (t-BuOK) in dimethylsulfoxide (DMSO) gave methylisoeugenol with 87.15% yield and 98.10% purity. Oxidation of methylisoeugenol usingpotassium dichromate (K 2 Cr 2 O 7 ) was performed catalyst transfer phase (CTP) system of polysorbate 80 to 83.40% 3.4-dimethoxybenzaldehyde yield and 90.20% purity. Reduction of 3.4-dimethoxybenzaldehyde with sodium borohidrat (NaBH 4 )produced 98% yield. Halogenation of 3,4-dimethoxybenzyl alcohol by SOCl 2 to 3,4-dimethoxybenzyl chloride followed bynitrilisation using sodium cyanide produced 3.4-dimethoxybenzyl cyanide with 83.90% purity after reflux for 20 hours.


clove leave oil, eugenol, isoflavone, nitrilization

Full Text:



Faria, T.J., Silva, L.G.F., Filho, J.D.S., Chiari, E & Oliveira, A.B. 2005. Synthesis and trypanocidal activity of 7,2’-dioxygenated isoflavones and oxypropanolamine derives. J Braz Chem Soc 16(6B): 1415-1419.

Kampköttera, A., Chovoloua, Y., Kulawika, A., Röhrdanzc, E., Weberb, N., Prokschb, P & Wätjena, W. 2008. soflavone daidzein possesses no antioxidant activities in cell-free assays but induces the antioxidant enzyme catalase. Nutr Res 28: 0–628.

Liao, S.Y., Chen, J.C., Qian, L., Shen, Y & Zheng, C. 2008. QSAR, Action mechanism and molecular design of favone and isoflavone derivatives with cytotoxicity against HeLa. Eur J Med Chem 43: 2159–2170.

Rukachaisirikul, T., Innok, P., Aroonrerk, N., Boonam-nuaylap, W., Limrangsun, S., Boonyon, C., Woonjina, U & Suksamrarn, A. 2007. Antibacterial pterocarpans from erythrina subumrans. J Etnopharmacol 110(1): 171–175.

Selepe, M.A., Drewes, S.E & van Heerden, F.R. 2010. Total synthesis of the pyranoisoflavone kraussianone 1 and related Isoflavones. J Nat Prod 73(10): 1680–1685.

Soidinsalo, O. 2007. Synthesis of Isoflavone Conjugates, Dissertation, Department of Chemistry, Faculty of Science. Finland: University of Helsinki.

Thoruwa, C.L., Song, T.T., Hu, J., Simon, A.L & Murphy, P.A. 2003. A simple synthesis of 7,4’-dihydroxy-6-methoxyisoflavone, glycitein, the Third Soybean Isoflavone. J Nat Prod 66: 149–151.



  • There are currently no refbacks.

Copyright (c) 2014 Andi Hairil Alimuddin, Sabirin Matsjeh, Chairil Anwar, Mustofa

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