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Gluconic acid

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Gluconic acid

Gluconic acid is an organic compound with molecular formula C6H12O7 and condensed structural formula HOCH2(CHOH)4CO2H. A white solid, it forms the gluconate anion in neutral aqueous solution. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Some drugs are injected in the form of gluconates.

The chemical structure of gluconic acid consists of a six-carbon chain, with five hydroxyl groups positioned in the same way as in the open-chained form of glucose, terminating in a carboxylic acid group. It is one of the 16 stereoisomers of 2,3,4,5,6-pentahydroxyhexanoic acid.

Gluconic acid is typically produced by the aerobic oxidation of glucose in the presence of the enzyme glucose oxidase. The conversion produces gluconolactone and hydrogen peroxide. The lactone spontaneously hydrolyzes to gluconic acid in water.

Variations of glucose (or other carbohydrate-containing substrate) oxidation using fermentation. or noble metal catalysis.

Gluconic acid was first prepared by Hlasiwetz and Habermann in 1870 and involved the chemical oxidation of glucose. In 1880, Boutroux prepared and isolated gluconic acid using the glucose fermentation.

The production of gluconic acid by deep-tank fermentation (aerated, pH controlled, and stirred >1000 L tanks) of the filamentous fungi Aspergillus niger in 1929, for use as a food acidity regulator and cleaning agent, was the first successful use of deep-tank fermentation by Pfizer. This expertise later led to Pfizer's successful use of deep-tank fermentation of Penicillium fungi in February 1944, to rapidly scale up penicillin production, resulting in sufficient penicillin to treat the American and British battle casualties of the June 6th Allied D-Day invasion of World War II.

Gluconic acid occurs naturally in fruit, honey, and wine. As a food additive (E574), it is now known as an acidity regulator.

The gluconate anion chelates Ca2+, Fe2+, K+, Al3+, and other metals, including lanthanides and actinides. It is also used in cleaning products, where it dissolves mineral deposits, especially in alkaline solution.

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