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 waste waters, was synthesized by reducing 3, 4-dihydroxyphenylacetic acid with LiAlH(4) in tetrahydrofuran under refluxing for 2 h. The yield of reaction was 82.8%. The spectroscopic and HPLC data of the synthesized compound proved to coincide fully with those of a pure sample obtained by the chromatographic recovery from olive oil mill waste waters (yield = 91 mg/L). This synthetic method appears to be the most convenient compared with those reported in the literature and is more convenient than the chromatographic recovery. The tri- and diacetyl derivatives of the synthetic compound were also prepared for structure-bioactivity relationship studies. A brief discussion is given on the economical and ecological aspects regarding the production of hydroxytyrosol.
Capasso
R
R
Dipartimento di Scienze Chimico-Agrarie, Università di Napoli "Federico II", Italy. capasso@unina.it
Evidente
A
A
Avolio
S
S
Solla
F
F
D000383:Agriculture; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D005511:Food Handling; D000069463:Olive Oil; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D010938:Plant Oils / Q000737:chemistry; D014865:Waste Disposal, Fluid
D000975:Antioxidants; D000069463:Olive Oil; D010938:Plant Oils; C005975:3,4-dihydroxyphenylethanol; D010626:Phenylethyl Alcohol