A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters

Hydroxytyrosol, a polyphenol with very interesting antioxidant properties, which naturally occurs in virgin olive oil and mainly in olive oil mill was te waters, was synthesized by reducing 3,4-dihydroxyphenylacetic acid with LiAIH(4) in tetrahydrofuran under refluxing for 2 h. The yield of reaction was 82.8%. The spectroscopic and HPLC data of the synthesized compound prov ed to coincide fully with those of a pure sample obtained by the chromatogr aphic recovery from olive oil mill waste waters (yield = 91 mg/L). This syn thetic method appears to be the most convenient compared with those reporte d in the literature and is more convenient than the chromatographic recover y. The tri- and diacetyl derivatives of the synthetic compound were also pr epared for structure-bioactivity relationship studies. A brief discussion i s given on the economical and ecological aspects regarding the production o f hydroxytyrosol.