SYNTHESIS, CHARACTERIZATION AND ANTIOXIDANT ACTIVITY OF 7-HYDROXY-3',4'-DIMETHOXYFLAVONE

https://doi.org/10.22146/ijc.21355

Elfi Susanti VH(1*), Sabirin Matsjeh(2), Tutik Dwi Wahyuningsih(3), Mustofa Mustofa(4), Tri Redjeki(5)

(1) Department of Chemistry, PMIPA FKIP, Sebelas Maret University, Jl. Ir Sutami 36 A Surakarta 53126
(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
(4) Faculty of Medicine, Universitas Gadjah Mada, Jl. Sekip Utara Yogyakarta 55281
(5) Department of Chemistry, PMIPA FKIP, Sebelas Maret University, Jl. Ir Sutami 36 A, Surakarta 53126
(*) Corresponding Author

Abstract


Synthesis of flavones and their derivatives has attracted considerable attention due to their significant pharmaceutical effects. 7-hydroxy-3',4'-dimethoxyflavone has been synthesized and its antioxidant activity has been investigated. Flavone was synthesized by oxidative cyclization of chalcone. 2',4'-dihydroxy-3,4-dimethoxychalcone was prepared by Claisen-Schmidt condensation of 2,4-dihydroxyacetophenones with 3,4-dimethoxybenzaldehydes in the presence of aqueous solution of sodium hydroxide and ethanol at room temperature. Oxidative cyclization of 2',4'-dihydroxy-3,4-dimethoxychalcone was done by using I2 catalyst in DMSO to form 7-hydroxy-3',4'-dimethoxyflavone. The synthesized compounds were characterized by means of their UV-Vis, IR, 1H-NMR and 13C-NMR spectral data. The compound was tested for their antioxidant activities by DPPH method.

Keywords


Flavone; chalcone; Claisen-Schmidt condensation; Antioxidant activity

Full Text:

Full Text PDF


References

[1] Murthy, Y.L.N., Viswanath, I.V.K., and Pandit, E.N., 2010, Int. J. ChemTech Res., 2, 2, 1097–1101.

[2] Mostahar, S., Katun, P., and Islam, A., 2007, J. Biol. Sci., 7, 3, 514–519.

[3] Theja, D.N., Choudary, T.P., Reddy, M.I., Avss, G., and Reddy, K.U., 2011, Int. J. Pharm. Pharm. Sci., 3, 2, 51–54.

[4] Alam, S., and Mostahar, S., 2005, J. Appl. Sci., 5, 2, 327–333.

[5] Middleton, E.Jr., Kandaswami, C., and Theoharides, T.C., 2000, Pharmacol. Rev., 52, 4, 673–751.

[6] Ares, J.J., Outt, P.E., Kakodkar, S.V., Buss, R.C., and Geiger, J.C., 1993, J. Org. Chem., 58, 27, 7903–7905.

[7] Ganguly, A.K., Kaur, S., Mahata, P.K., Biswas, D., Pramanik, B.N., and Chan, T.M., 2005, Tetrahedron Lett., 46, 23, 4119–4121.

[8] Zambare, A.S., Sangshetti, J.N., Kokare, N.D., and Shinde, D.B., 2009, Chin. Chem. Lett., 20, 2, 171–174.

[9] Kabalka, G.W., and Mereddy, A.R., 2005, Tetrahedron Lett., 6, 37, 6315–6317.

[10] Kumar, S., and Sharma, D., 2011, Orient. J. Chem., 27, 2, 761–763.

[11] Jayapal, M.R., Prasad, K.S., and Sreedhar, N.Y., 2010, Int. J. Pharm. Biol. Sci., 1, 4, 361–366.

[12] Doshi, A.K., Soni, P.A., and Ghiya, B.J., 1986, Indian J. Chem., 258, 759.

[13] Mostahar, S., Alam, S., and Islam, A., 2006, J. Serb. Chem. Soc., 72, 4, 321–329

[14] Tagashira, M., and Ohtake Y., 1998, Planta Med., 64, 555–558.



DOI: https://doi.org/10.22146/ijc.21355

Article Metrics

Abstract views : 3040 | views : 2904


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.

Web Analytics View The Statistics of Indones. J. Chem.