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Oxalic acid is an organic acid with the IUPAC name ethanedioic acid and formula HO2C−CO2H. It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels. It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.
Oxalic acid has much greater acid strength than acetic acid. It is a reducing agent[7] and its conjugate base, known as oxalate (C2O2−4), is a chelating agent for metal cations. Typically, oxalic acid occurs as the dihydrate with the formula C2H2O4·2H2O.
At least two pathways exist for the enzyme-mediated formation of oxalate. In one pathway, oxaloacetate, a component of the Krebs citric acid cycle, is hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase:
[O2CC(O)CH2CO2]2− + H2O → C2O2−
4 + CH3CO−
2 + H+
It also arises from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol.
Calcium oxalate is the most common component of kidney stones. Early investigators isolated oxalic acid from wood-sorrel (Oxalis). Members of the spinach family and the brassicas (cabbage, broccoli, brussels sprouts) are high in oxalates, as are sorrel and umbellifers like parsley. Rhubarb leaves contain about 0.5% oxalic acid, and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. Similarly, the Virginia creeper, a common decorative vine, produces oxalic acid in its berries as well as oxalate crystals in the sap, in the form of raphides. Bacteria produce oxalates from oxidation of carbohydrates.
Plants of the genus Fenestraria produce optical fibers made from crystalline oxalic acid to transmit light to subterranean photosynthetic sites.
Carambola, also known as starfruit, also contains oxalic acid along with caramboxin. Citrus juice contains small amounts of oxalic acid. Citrus fruits produced in organic agriculture contain less oxalic acid than those produced in conventional agriculture.
The formation of naturally occurring calcium oxalate patinas on certain limestone and marble statues and monuments has been proposed to be caused by the chemical reaction of the carbonate stone with oxalic acid secreted by lichen or other microorganisms.
Many soil fungus species secrete oxalic acid, resulting in greater solubility of metal cations, increased availability of certain soil nutrients, and can lead to the formation of calcium oxalate crystals.
Oxidized bitumen or bitumen exposed to gamma rays also contains oxalic acid among its degradation products. Oxalic acid may increase the leaching of radionuclides conditioned in bitumen for radioactive waste disposal.
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