or view the list of known compounds. Note that all formulas are case-sensitive. [13], Plants of the genus Fenestraria produce optical fibers made from crystalline oxalic acid to transmit light to subterranean photosynthetic sites.[28]. Oxalic acid has several uses, and it is regularly used as an ingredient in both cleaners and pharmaceuticals. [19] Because the anhydrous material is both acidic and hydrophilic (water seeking), it is used in esterifications. Its more-common dihydrous form has a molar mass of 126.07 g/mol. Oxalic acid dihydrate | C2H6O6 | CID 61373 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. common chemical compounds. ›› Calculate the molecular weight of a chemical compound. Oxalic acid, or H2C2O2, is a highly acidic, organic compound. Bjerrum, J., et al. CRC Handbook of Chemistry and Physics, 95th Edition (95 edition). Henry Enfield Roscoe and Carl Schorlemmer, ed.s, Torbern Bergman with Johan Afzelius (1776), This page was last edited on 31 October 2020, at 05:43. 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. Oxalic acid occurs naturally in both plants and animals, and in its solid form, it is an odorless, white solid. Oxalic acid (Crab Acid) is mainly manufactured by the oxidation of carbohydrates or glucose using nitric acid or air in the presence of vanadium pentoxide. If it is in its solid form, its molar mass is 90.03 g/mol. [32][33], Oxidized bitumen or bitumen exposed to gamma rays also contains oxalic acid among its degradation products. Anhydrous oxalic acid exists as two polymorphs; in one the hydrogen-bonding results in a chain-like structure whereas the hydrogen bonding pattern in the other form defines a sheet-like structure. Approximately 120,000 tonnes are produced annually.[13]. This site explains how to find molar mass. [12] This experiment may represent the first synthesis of a natural product.[13]. ›› More information on molar mass and molecular weight. Oxalic acid may increase the leaching of radionuclides conditioned in bitumen for radioactive waste disposal.[34]. Try another chemical formula , or view the list of known compounds. [21], Oxalic acid's pKa values vary in the literature from 1.25-1.46 and 3.81-4.40. Eiichi, Yonemitsu; Tomiya, Isshiki; Tsuyoshi, Suzuki and Yukio, Yashima "Process for the production of oxalic acid", CS1 maint: multiple names: authors list (. [25], At least two pathways exist for the enzyme-mediated formation of oxalate. This is how to calculate molar mass (average molecular weight), which is based on isotropically weighted averages. Name: Oxalic Acid. The preparation of salts of oxalic acid (crab acid) from plants had been known, at the latest, since 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from sorrel. It has a pH of 1.3, so protective gloves, eye gear and clothing must be worn when handling this substance. Using the chemical formula of the compound and the periodic table of elements, we can add up the atomic weights and calculate molecular weight of the substance. 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. Thermal decomposition of these oxalates gives the oxides, which is the most commonly marketed form of these elements. Developed in the Netherlands, an electrocatalysis by a copper complex helps reduce carbon dioxide to oxalic acid;[18] this conversion uses carbon dioxide as a feedstock to generate oxalic acid. C 12 x 2 = 24 H 1 x 2 = 2 Oxalic Acid. [14] A newer method entails oxidative carbonylation of alcohols to give the diesters of oxalic acid: These diesters are subsequently hydrolyzed to oxalic acid. The mass and molarity of chemical compounds can be calculated based on the molar mass of the compound. Oxalic acid is an organic compound with the formula C2H2O4. [9], In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman[10] produced oxalic acid by reacting sugar with concentrated nitric acid; Scheele called the acid that resulted socker-syra or såcker-syra (sugar acid). E.g. The atomic weights used on this site come from NIST, the National Institute of Standards and Technology. CRC Press. Boca Raton; London; New York: CRC Press. Pyrolysis of sodium formate (ultimately prepared from carbon monoxide), leads to the formation of sodium oxalate, easily converted to oxalic acid. ›› oxalic acid molecular weight. Symptoms and effects include a burning sensation, cough, wheezing, laryngitis, shortness of breath, spasm, inflammation and edema of the larynx, inflammation and edema of the bronchi, pneumonitis, pulmonary edema. Get the latest public health information from CDC: https://www.coronavirus.gov. molar mass and molecular weight. Molar mass of NaCl is 58.443, how many grams is 5 mole NaCl? [15] Its utility in rust removal agents is due to its forming a stable, water-soluble salt with ferric iron, ferrioxalate ion. Enter a chemical formula: Browse the list of common chemical compounds. (Ed.). Oxalic acid can also cause joint pain by formation of similar precipitates in the joints. [16], The hydrated solid can be dehydrated with heat or by azeotropic distillation.[17]. It is used in bleaches, especially for pulpwood. ^a Unless otherwise cited, all measurements are based on raw vegetable weights with original moisture content. Oxalic acid | (COOH)2 or HOOCCOOH or C2H2O4 | CID 971 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. It is also used in baking powder[13] and as a third reagent in silica analysis instruments. CRC Handbook of Chemistry and Physics, 100th Edition (100 edition). It forms esters such as dimethyl oxalate (m.p. New York: John Wiley Sons, 1981-1982., p. 4936. Oxalic acid is a relatively strong acid, despite being a carboxylic acid: Oxalic acid undergoes many of the reactions characteristic of other carboxylic acids. ], Clayton, G. D. and F. E. Clayton (eds.). The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate,[49] the main component of calcium kidney stones. [20] It forms an acid chloride called oxalyl chloride. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid. (Ed.). To complete this calculation, you have to know what substance you are trying to convert. [30][31], 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. Ingestion of ethylene glycol results in oxalic acid as a metabolite which can also cause acute kidney failure. Members of the spinach family and the brassicas (cabbage, broccoli, brussels sprouts) are high in oxalates, as are sorrel and umbellifers like parsley. Citrus fruits produced in organic agriculture contain less oxalic acid than those produced in conventional agriculture[29]. A common request on this site is to convert grams to moles. Browse the list of [35] LDH catalyses the conversion of pyruvate to lactic acid (end product of the fermentation (anaerobic) process) oxidising the coenzyme NADH to NAD+ and H+ concurrently. [37], Oxalic acid is used to clean minerals.[38][39]. This is not the same as molecular mass, which is the mass of a single molecule of well-defined isotopes. Its more-common dihydrous form has a molar mass of 126.07 g/mol. Carambola, also known as starfruit, also contains oxalic acid along with caramboxin. (2014). [45], In humans, ingested oxalic acid has an oral LDLo (lowest published lethal dose) of 600 mg/kg. Oxalic acid in concentrated form can have harmful effects through contact and if ingested. Oxalic acid's main applications include cleaning or bleaching, especially for the removal of rust (iron complexing agent). It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous. The formula weight is simply the weight in atomic mass units of all the atoms in a given formula. Oxalic acid is an ingredient in some tooth whitening products. [11], In 1824, the German chemist Friedrich Wöhler obtained oxalic acid by reacting cyanogen with ammonia in aqueous solution. grams = 58.443 × 5 = 292.215 (g) In one pathway, oxaloacetate, a component of the Krebs citric acid cycle, is hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase:[26]. By 1784, Scheele had shown that "sugar acid" and oxalic acid from natural sources were identical. Error: oxalic acid is unknown. Try another chemical formula, Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction. 3rd ed. (1958) Stability Constants, Chemical Society, London. To find the molar mass, we just multiply the atomic mass of each element by the number of that element in the molecule, and then add the totals for each element together. ), The Secret Science of Solving Crossword Puzzles, Racist Phrases to Remove From Your Mental Lexicon. Rombauer, Rombauer Becker, and Becker (1931/1997). Citrus juice contains small amounts of oxalic acid. If it is in its solid form, its molar mass is 90.03 g/mol. Hydrated lanthanide oxalates form readily in very strongly acidic solutions in a densely crystalline, easily filtered form, largely free of contamination by nonlanthanide elements. Oxalate, the conjugate base of oxalic acid, is an excellent ligand for metal ions, e.g. As cancer cells preferentially use anaerobic metabolism (see Warburg effect) inhibition of LDH has been shown to inhibit tumor formation and growth,[36] thus is an interesting potential course of cancer treatment. Formula weights are especially useful in determining the relative weights of reagents and products in a chemical reaction. In modern times, it is produced synthetically using carbon and petroleum products. Festival of Sacrifice: The Past and Present of the Islamic Holiday of Eid al-Adha. Error: oxalic acid is unknown. [47], Oxalate may enter cells where it is known to cause mitochondrial dysfunction.[48]. Molar Mass: 90.0349. Note that all formulas are case-sensitive. All data not specifically annotated is from, Institute for Occupational Safety and Health, National Institute for Occupational Safety and Health, "Om Rhabarber-jordens bestånds-delar, samt sått at tilreda Acetosell-syran", "OpenLibrary.org: The Private Life of Plants", "Organic Acids Concentration in Citrus Juice from Conventional versus Organic Farming", "Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression", Exploring New Methods for Varroa Mite Control, "Nutrient Data : Oxalic Acid Content of Selected Vegetables", "CDC – Immediately Dangerous to Life or Health Concentrations (IDLH): Oxalic acid – NIOSH Publications and Products", "Oxalate induces mitochondrial dysfunction and disrupts redox homeostasis in a human monocyte derived cell line", EMEA Committee for veterinary medicinal products, oxalic acid summary report, December 2003, Table: Oxalic acid content of selected vegetables (USDA), Alternative link: Table: Oxalic Acid Content of Selected Vegetables (USDA), About rhubarb poisoning (The Rhubarb Compendium), Oxalosis & Hyperoxaluria Foundation (OHF) The Oxalate Content of Food 2008 (PDF), Oxalosis & Hyperoxaluria Foundation (OHF) Diet Information, Calculator: Water and solute activities in aqueous oxalic acid, https://en.wikipedia.org/w/index.php?title=Oxalic_acid&oldid=986334005, Short description is different from Wikidata, Chemical articles with multiple compound IDs, Multiple chemicals in an infobox that need indexing, Chemical articles with multiple CAS registry numbers, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Wikipedia articles needing clarification from December 2018, Creative Commons Attribution-ShareAlike License, 189 to 191 °C (372 to 376 °F; 462 to 464 K).