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
Chemistry of ascorbic acid catalytically hydrogenated to sorbitol, which is then oxidized by the microorganism "Acetobacter suboxydans" to sorbose. Only one of the six hydroxy groups is oxidized by this enzymatic reaction. From this point, two routes are available. Treatment of the product with acetone in the presence of an acid catalyst converts four of the remaining hydroxyl groups to acetals. The unprotected hydroxyl group is oxidized to the carboxylic acid by reaction with the catalytic oxidant TEMPO (regenerated by sodium hypochlorite — bleaching solution). Historically, industrial preparation via the Reichstein process used potassium permanganate as the bleaching solution. Acid-catalyzed hydrolysis of this product