A New Process for Preparation of Hydroxytyrosol
Hydroxytyrosol is one of the major natural phenolic compounds, mainly in virgin olive oil and the wastewater generated from olive oil processing. Based on its strong antioxidation, hydroxytyrosol is widely used in medical treatment, food, beauty, and othe
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A New Process for Preparation of Hydroxytyrosol Yinghao Gao, Xijuan Liang, Yuanmou Chen, Fei Hu, Weizhu Liu, Peng Yu and Erbing Hua
Abstract Hydroxytyrosol is one of the major natural phenolic compounds, mainly in virgin olive oil and the wastewater generated from olive oil processing. Based on its strong antioxidation, hydroxytyrosol is widely used in medical treatment, food, beauty, and other industries. Its diverse biological activities have for a long time attracted considerable interest of synthetic and pharmacological areas. In this paper, the new process of hydroxytyrosol synthesis has been explored, which starts from catechol protection, followed by Friedel–Crafts reaction with ethyl oxalyl monochloride, then the Wolff-Kishner-Huang reaction and reduction reaction with LAH, and finally deprotection. The target compound was obtained by five-step reaction with an overall yield of 23 %. The title compound was characterized on the basis of 1 H NMR spectral. Keywords Natural
Hydroxytyrosol Synthesis New process
70.1 Introduction Hydroxytyrosol (3,4-dihydroxyphenylethanol) is primarily found in fruits and leaves of olive and has been reported to exert several biological and pharmacological activities [1]. It was first discovered and extracted from the wastewater that resulted when green olives were rinsed in the process of making olive oil [2–4] (Fig. 70.1). For decades olive oil has been known for its many healthy properties. It has long been noted that the Mediterranean diet has been associated with a lower Y. Gao X. Liang Y. Chen F. Hu W. Liu P. Yu E. Hua (&) Key Laboratory of Industrial Microbiology, Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, People’s Republic of China e-mail: [email protected]
T.-C. Zhang et al. (eds.), Proceedings of the 2012 International Conference on Applied Biotechnology (ICAB 2012), Lecture Notes in Electrical Engineering 250, DOI: 10.1007/978-3-642-37922-2_70, Ó Springer-Verlag Berlin Heidelberg 2014
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690 Fig. 70.1 Structures of hydroxytyrosol
Y. Gao et al. HO
OH
HO
incidence of cardiovascular disease and certain cancers than the diet of other Western countries [5]. And since extra-virgin olive oil is the principal source of fat in the Mediterranean diet and has been identified as an important contributor to the reduced mortality associated with this diet, researchers began studying olive oil, looking for the compound that was responsible for the anti-inflammatory and cholesterol-lowering effects [6]. That’s when they found hydroxytyrosol—the polyphenol thought to be responsible for olive oil’s anti-inflammatory and antioxidant effects [7]. Its ability to absorb free radicals and protect cells and mitochondria [8] from damage is quite impressive. The antioxidant activity is the most studied property of hydroxytyrosol. The interest of hydroxytyrosol is based on its remarkable pharmacological and antioxidant activities. Reactive oxygen species, which are continuously being formed as a resul
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