SYNTHESIS 7-O-CARBOXYMETHYL-3’,4’-DIMETHOXYISOFLAVONE

https://doi.org/10.22146/ijc.21337

Andi Hairil Alimuddin(1*), Sabirin Matsjeh(2), Chairil Anwar(3), Mustofa Mustofa(4)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Tanjungpura, Jl. Jenderal Ahmad Yani Pontianak, Kalimantan Barat
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Jl. Sekip Utara, Yogyakarta 55281
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Jl. Sekip Utara, Yogyakarta 55281
(4) Pharmacology Division, Faculty of Medicine, Universitas Gadjah Mada, Jl. Farmaco Yogyakarta
(*) Corresponding Author

Abstract


Synthesis of 7-O-carboxymethyl-3',4'-dimethoxyisoflavone from 7-hydroxy-3',4'-dimethoxyisoflavone derived from eugenol had been done. 7-hydroxy-3',4'-dimethoxyisoflavone was first converted into 7-O-ethoxycarbonylmethyl-3',4'-dimethoxyisoflavone via substitution of hydroxyl group at 7-O position by ethyl-2 chloro acetate through bimolecular nucleophilic substitution reaction (SN2). Hydrolysis of ester group of 7-O-ethoxycarbonylmethyl-3',4'-dimethoxyisoflavone using KOH produce 7-O-carboxymethyl-3',4'-dimethoxyisoflavone in 93.4% yield as a white solid with melting point of 155-159 °C.

Keywords


eugenol; isoflavone; SN2 reaction

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References

[1] Liggins, J., Bluck, L.J., Runswick, S., Atkinson, C., Coward, W.A., and Bingham, S.A., 2000, J. Nutr. Biochem., 11, 6, 326–331.

[2] Kampkötter, A., Chovolou, Y., Kulawik, A., Röhrdanz, E., Weber, N., Proksch, P., and Wätjen, W., 2008, Nutr. Res., 28, 9, 620–628.

[3] Rukachaisirikul, T., Innok P, Aroonrerk, N, Boonamnuaylap, W., Limrangsun, S., Boonyon, C., Woonjina, U., and Suksamrarn, A., 2007, J. Ethnopharmacol., 110, 1, 171–175.

[4] Alekel, D.L., Alyson, St.G., Charles, T.P., Kathy, B.H., Jeanne, W.S., and Thoshiya, T., 2000, Am. J. Clin. Nutr., 72, 3, 844–852.

[5] Choi, E.J., and Kim, G-H, 2008, Phytomedicine, 15, 9, 683–690.

[6] Kohen, F., Gayer, B., Kulik, T., Frydman, V., Nevo, N., Katzburg, S., Limor, R., Sharon, O., Stern, N., and Somjen, D., 2007, J. Med. Chem., 50, 25, 6405–6410.

[7] Alimuddin, A.H., Darussalam, M.I., Matsjeh, S., Anwar, C., Mustofa, and Sholikha, E.N., 2011, Indo. J. Chem., 11, 2, 163–168.

[8] Soidinsalo, O., 2007, Synthesis of Isoflavone Conjugates, Dissertation, Faculty of Science, University of Helsinki, Finland.



DOI: https://doi.org/10.22146/ijc.21337

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