Chemistry of ascorbic acid Haworth and Szent-Györgyi, respectively. Ascorbic acid is a vinylogous carboxylic acid and forms the ascorbate anion when deprotonated on one of the hydroxyls. This property is characteristic of reductones: enediols with a carbonyl group adjacent to the enediol group, namely with the group –C(OH)=C(OH)–C(=O)–. The ascorbate anion is stabilized by electron delocalization that results from resonance between two forms: For this reason, ascorbic acid is much more acidic than would be expected if the compound contained only isolated hydroxyl groups. The ascorbate anion forms salts, such as sodium ascorbate, calcium ascorbate, and potassium ascorbate. Ascorbic acid can also react with
Vitamin C efficiency decreases as amounts increase. Intravenous administration bypasses this. Doing so makes it possible to achieve plasma concentrations of 5 to 10 millimoles/liter (mmol/L), which far exceed the approximately 0.2 mmol/L limit from oral consumption. The theories of mechanism are contradictory. At high tissue concentrations ascorbic acid is described as acting as a pro-oxidant, generating hydrogen peroxide (HO) to kill tumor cells. The same literature claims that ascorbic acid acts as an antioxidant, thereby reducing the adverse effects of chemotherapy and radiation therapy. Research continues in this field, but a 2014 review concluded: "Currently, the use of high-dose intravenous vitamin