Pemanfaatan Minyak Daun Cengkeh untuk Sintesis 3,4-dimetoksibenzil Sianida sebagai Bahan Dasar Sintesis Isoflavon
Abstract
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.
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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.
DOI: http://dx.doi.org/10.31258/jni.15.01.68-74
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