Transformation of Eugenol and Safrole into Hydroxychavicol

https://doi.org/10.22146/ijc.21227

Budi Arifin(1*), Dumas Flis Tang(2), Suminar Setiati Achmadi(3)

(1) Department of Chemistry, Bogor Agricultural University, Kampus IPB Dramaga, Bogor 16680
(2) Department of Chemistry, Bogor Agricultural University, Kampus IPB Dramaga, Bogor 16680
(3) Department of Chemistry, Bogor Agricultural University, Kampus IPB Dramaga, Bogor 16680
(*) Corresponding Author

Abstract


Hydroxychavicol is found in betel leaf at low concentration and is reported to have antibacterial, anti-inflammatory, antioxidant, anticancer, and antimutagenic activities. This study aimed to synthesize hydroxychavicol from eugenol and safrole. Isolation of eugenol from clove oil by alkaline extraction method gave 71% yield, while the isolation of safrole from lawang oil by alkaline extraction method, followed by purification using preparative thin layer chromatography, gave 7% yield. Eugenol demethylation and safrole demethylenation with AlCl3 reagent were successfully produced hydroxychavicol. The yields were 28% and 24%, respectively. Mechanisms of the synthesis are proposed in this article.

Keywords


demethylation; demethylenation; eugenol; hydroxychavicol; safrole

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References

[1] Nalina, T., and Rahim, Z.H., 2007, Am. J. Bichem. Biotechnol., 3(1), 10–15.

[2] Sharma, S., Khan, I.A., Ali, I., Ali, F., Kumar, M., Kumar, A., Johri, R.K., Abdullah, S.T., Bani, S., Pandey, A., Suri, K.A., Gupta, B.D., Satti, N.K., Dutt, P., and Qazi, G.N., 2009, Antimicrob. Agents Chemother., 53(1), 216–222.

[3] Ali, I., Khan, F.G., Suri, K.A., Gupta, B.D., Satti, N.K., Dutt, P., Afrin, F., Qazi, G.N., and Khan I.A., 2010, Ann. Clin. Microbiol. Antimicrob., 9, 7.

[4] Pandey, A., Bani, S., Dutt, P., and Suri, K.A., 2010, Cytokine, 49(1), 114–121.

[5] Nakagawa, Y., Suzuki, T., Nakajima, K., Ishii, H., and Ogata, A., 2009, Chem. Biol. Interact., 180(1), 89–97.

[6] Pandey, A., and Bani, S., 2010, J. Neuroimmunol., 226(1-2), 48–58.

[7] National Library of Medicine, Hazardous Substances Data Bank (HSDB), http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB, accessed on Nov 16, 2012.

[8] Vera, W.J., and Banerjee, A.K., 2007, ARKIVOC, vii, 8–11.

[9] Gopalakrishnan, G., Kasinath, V., Singh, N.D.P., Thirumurungan, R., Raj, S.S.S., and Shanmugam, G., 2000, Molecules, 5(6), 880–885.

[10] Villegas, A.M., Catalan, L.E., Venegas, I.M., Garcia, J.V., and Altamirano, H.C., 2011, Molecules, 16(6), 4632–4641.

[11] Carrasco, H., Raimondi, M., Svetaz, L., Di Liberto, M., Rodriguez, M.V., Espinoza, L., Madrid, A., and Zacchino, S., 2012, Molecules, 17(1), 1002–1024.

[12] Catalan, L.E., Villegas, A.M., Liber, L.T., Garcia, J.V., Fritis, M.C., and Altamirano, H.C., 2010, J. Chil. Chem. Soc., 55(2), 219–222.

[13] Vass, A., Dudás, J., Borbély, L., Haász, F., and Jekkel, P., 2011, European Patent EP 1831144 B1.

[14] Du, Z-T., Lu, J., Yu, H-R., Xu, Y., and Li, A-P., 2010, J. Chem. Res., 34(4), 222–227.

[15] Zhang, Y., Du, M., Yu, Y-F., Xu, S-X., Zhao, S-C., and Wang, H-T., 2014, J. Chem. Pharm. Res., 6(1), 232–236.

[16] Asnawi, A., Nawawi, A., Kartasasmita, R.E., and Ibrahim, S. 2011, ITB J. Sci., 43A(1), 43–50.

[17] Mohammed, M.J., and Al-Bayati, F.A., 2009, Phytomedicine, 16(6-7), 632–637.

[18] Jirovetz, L., Buchbauer, G., Stoilova, I., Stoyanova, A., Krastanov, A., and Schmidt, E., 2006, J. Agric. Food Chem., 54(17), 6303–6307.

[19] Sudarma, I.M., Ulfa, M., and Sarkono, 2009, Indones. J. Chem., 9(2), 267-270.

[20] Bihari, C.G., Manaswini, B., Kumar, T.S., Kumar, J.P., and Ranjan, M.S., 2011, Int. J. Chem. Anal. Sci., 2(1), 3–6.

[21] Erowid H.T.M., 2005, Safrol FAQ. http://www.erowid.org/archive/rhodium/chemistry/saf rolfaq.html, accessed on Nov 16, 2012.

[22] Kraft, P., and Eichenberger, W., 2003, Eur. J. Org. Chem., 19, 3745–3743.

[23] Fierro, R.S., Maquilang, Q.M.A., Sanjorjo, R.A.S., Tradio, M.D., Shem, C.C., and Ragasa, C.Y., 2012, J. Med. Plants Res., 6(11), 2146–2149.



DOI: https://doi.org/10.22146/ijc.21227

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