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398    Cha pte r  F o u r tee n

                   Hydroxytyrosol is the olive phenol most studied because it is
               characterized by major bioantioxidant activity. In ripe olives, it is
                                                              –1
               present in quantities ranging from 1.0 and 2.9 g per 100 g  of dry mat-
               ter (Amiot et al. 1986; Romero et al. 2002).
                                                                      –1
                   In the virgin olive oil, total phenol ranged from 50 to 500 mg kg  of
               oil; the final content is the result of several factors including cultivar
               and quality of the olives, degree of maturation, climate, time and con-
               dition of olive storage, and oil-extraction system (Montedoro and Garo-
               falo 1984; Solinas 1987; Bruni et al. 1994; Caponio et al. 1999). Actually,
               only one or two of the total phenols present in olives are found in virgin
               oil because the majority of them remain in the wastewaters and in the
               pomace (Rodis et al. 2002; Di Giovacchino et al. 1993).
                   During the first phase of the olive oil–extraction process, during
               the initial grinding and the thermomixing of the olive paste, chemical
               and enzymatic reactions are carried out that degrade at least 80 percent
               of the olive’s complex polyphenols. In the three-phase system, it is
               estimated that the major part of olive polyphenols, especially
               hydroxytyrosol, relocate themselves in the wastewater (Niaounakis
               and Halvadakis, 2004). Hydroxytyrosol is very abundant in olive mill
               wastewaters in the free form or as a component of oleuropein, demeth-
               yloleuropein, verbascoside, and hydroxytyrosol-4-β-D-glucoside
               (Vásquez et al. 1987; Gutfinger 1998; Servili et al. 1999b; Capasso et al.
               1999; Visioli and Galli 1999).
                   On the contrary, in virgin olive oil, simple phenols are lower than
               complex phenols; principal simple phenols are hydroxytyrosol, tyro-
               sol and caffeic acid, p-coumaric, syringic and vanillic acids (Monte-
               doro et al. 1992a; Montedoro et al. 1992b; Limiroli et al. 1995).
                   When virgin oil is inedible, the refining process is necessary
               where almost all phenols are destroyed (Tiscornia et al. 1982). For the
               loss of natural antioxidants, refined olive oil is of lower quality than
               extra virgin olive oil.


          14.4  Antioxidant and Nutraceutical Properties
               In the best storage conditions, virgin olive oil has a protracted shelf
               life, up to almost 2 years. Accordingly, olive oil’s higher stability has
               been attributed to its phenolic content (De Leonardis and Macciola
               1998; Psomiadou and Tsimidou 2002).
                   It was repeatedly found that among olive polyphenols, o-diphenols,
               especially hydroxytyrosol and caffeic acid, are the most effective
               substances (Papadopoulos and Boskou 1991; Tsimidou et al. 1992;
               Baldioli et al. 1996). However, the monophenol tyrosol and its deriva-
               tives and p-hydroxybenzoic, o-coumaric, and p-coumaric acids have
               insufficient or no antioxidant effect (Litridou et al. 1997).
                   Hydroxytyrosol is a good antioxidant that is more effective than
               tocopherol, butylated hydroxytoluene (BHT), and other synthetic anti-
               oxidants permitted for use in foods (De Leonardis and Macciola 2008).
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