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

Andi Hairil Alimuddin (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Tanjungpura, Jl. Jenderal Ahmad Yani Pontianak, Kalimantan Barat)
Sabirin Matsjeh (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Jl. Sekip Utara, Yogyakarta 55281)
Chairil Anwar (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Jl. Sekip Utara, Yogyakarta 55281)
Mustofa Mustofa (Pharmacology Division, Faculty of Medicine, Universitas Gadjah Mada, Jl. Farmaco Yogyakarta)

Indonesian Journal of Chemistry
Vol 12, No 3 (2012)

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.