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Composition of tomatoes and tomato products in antioxidants (WG1) page 68<br />

__________________________________________________________________________________________<br />

- E 0 (pH7) = 280 mV for ascorbate .- + H + + e - ➔ ascorbate -<br />

HO<br />

E 0 (pH7) = -174 mV for dehydroascorbic acid + e - ➔ ascorbate .-<br />

CH2OH CH O O<br />

- O OH<br />

Ascorbate -<br />

- Stability :<br />

- Stable to air when dry<br />

- It is extremely unstable in aqueous solution. Indeed it is easily oxidized by air<br />

to dehydroascorbic acid (DHAA), and further compounds. The oxidation of AA to DHAA is<br />

reversible, but oxidation beyond DHAA is irreversible and is enhanced by alkaline pH and<br />

metals, especially copper and iron. The degradation processes of ascorbic acid are very<br />

complex and contain a number of oxidation/reduction and intermolecular rearrangement<br />

reactions (Deutsch 1998; Yuan and Chen 1998). Hence, procedures for stabilizing the vitamin<br />

in biologic samples involve acidification with the addition of a reducing agent and a metal<br />

chelator.<br />

7.2.3 Antioxidant properties<br />

- e-, - H+<br />

+ e-, + H+<br />

HO<br />

CH2OH CH O<br />

-.<br />

O<br />

O O<br />

Ascorbate .-<br />

Ascorbic acid is a well known reducing agent both in vivo and in vitro, thus being an<br />

antioxidant compound. In contrast to this role, AA also appears to act as a prooxidant under<br />

certain conditions in vitro, in particular in presence of ferric iron (Fe 3+ ). Indeed ascorbate can<br />

reduce ferric iron to ferrous iron (Fe 2+ ) which, in turn, can enter the Fenton reaction (figure<br />

12) to produce the very toxic hydroxyl radical.<br />

Fe 3+ + ascorbate - ➔ Fe 2+ + ascorbate -.<br />

Fe 2+ + H2O2 ➔ Fe 3+ + HO - + HO . (Fenton Reaction)<br />

Figure 12 : role of ascorbic acid in the production of hydroxyl radical<br />

- e-<br />

+ e-<br />

HO<br />

CH2OH CH O O<br />

O O<br />

dehydroascorbic acid

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