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Mesoxalic acid, also called oxomalonic acid or ketomalonic acid, is an
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with formula C3H2O5 or HO−(C=O)3−OH. Mesoxalic acid is both a
dicarboxylic acid In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids sho ...
and a ketonic acid. It readily loses two
proton A proton is a stable subatomic particle, symbol , H+, or 1H+ with a positive electric charge of +1 ''e'' elementary charge. Its mass is slightly less than that of a neutron and 1,836 times the mass of an electron (the proton–electron mass ...
s to yield the divalent
anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conve ...
, called mesoxalate, oxomalonate, or ketomalonate. These terms are also used for
salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...
containing this anion, such as sodium mesoxalate, Na2C3O5; and for
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
s containing the −C3O5− or −O−(C=O)3−O−
moiety Moiety may refer to: Chemistry * Moiety (chemistry), a part or functional group of a molecule ** Moiety conservation, conservation of a subgroup in a chemical species Anthropology * Moiety (kinship), either of two groups into which a society is ...
, such as diethyl mesoxalate, (C2H5)2C3O5. Mesoxalate is one of the oxocarbon anions, which (like
carbonate A carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula . The word ''carbonate'' may also refer to a carbonate ester, an organic compound containing the carbonate ...
and
oxalate Oxalate (IUPAC: ethanedioate) is an anion with the formula C2O42−. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na2C2O4), and several esters such as dimethyl ...
) consist solely of
carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon ma ...
and
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...
. Mesoxalic acid readily absorbs and reacts with water to form a product commonly called "mesoxalic acid monohydrate", more properly
dihydroxymalonic acid Dihydroxymalonic acid is an organic compound with formula C3H4O6 or HO-(C=O)-C(OH)2-(C=O)-OH, found in some plants such as alfalfa and in beet molasses. The compound is also called dihydroxymesoxalic acid and dihydroxypropanedioic acid. It can b ...
, HO−(C=O)−C(OH)2−(C=O)−OH. In product catalogs and other contexts, the terms "mesoxalic acid", "oxomalonic acid" and so on often refer to this "hydrated" compound. In particular, the product traded as "sodium mesoxalate monohydrate" is almost always
sodium dihydroxymalonate Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable is ...
.


Synthesis

Mesoxalic acid can be obtained synthetically by
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysi ...
of
alloxan Alloxan, sometimes referred to as ''alloxan hydrate'', is the name of the organic compound with the formula OC(N(H)CO)2C(OH)2. It is classified as a derivative of pyrimidine. The anhydrous derivative OC(N(H)CO)2CO is also known, as well as a dim ...
with
baryta Barium sulfate (or sulphate) is the inorganic compound with the chemical formula Ba SO4. It is a white crystalline solid that is odorless and insoluble in water. It occurs as the mineral barite, which is the main commercial source of barium and ...
water, by warming caffuric acidThe chemical structure of caffuric acid was given in Allen, W. F. (1932). The preparation and pyrolytic molecular rearrangment icof the 8-ethers of caffeine: And their conversion to 8-methyl and 8-ethylcaffeine. Ann Arbor, Mich.: Edwards Brothers. with lead acetate solution,Henry Enfield Roscoe (1888), ''A Treatise on Chemistry'', volume 3, part2 ''Organic Chemistry'', p. 161. D. Appleton and Co., New York or from
glyceryl diacetate Glyceryl diacetate is a food additive with the E number E1517. This diglyceride is more generally known as diacetin. It is the diester of glycerol and acetylating agents, such as acetic acid and acetic anhydride. It is a colorless, viscous and ...
and concentrated
nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...
in the cold. The product can be obtained also by oxidation of
tartronic acid Tartronic acid or 2-hydroxymalonic acid is an organic compound with the structural formula of HOHC(CO2H)2. This dicarboxylic acid is related to malonic acid. Its derivative, 2-methyltartronic acid, is isomalic acid. Uses Tartronic acid is best ...
or
glycerol Glycerol (), also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known ...
. Rosaria Ciriminna and Mario Pagliaro (2003), ''One-Pot Homogeneous and Heterogeneous Oxidation of Glycerol to Ketomalonic Acid Mediated by TEMPO''. Advanced Synthesis & Catalysis, volume 345, issue 3, Pages 383–388. {{doi, 10.1002/adsc.200390043 Since they are carried out in water, these procedures generally give the dihydroxy derivative. It is also prepared by the oxidation of glycerol with the help of
bismuth(III) nitrate Bismuth(III) nitrate is a salt composed of bismuth in its cationic +3 oxidation state and nitrate anions. The most common solid form is the pentahydrate. It is used in the synthesis of other bismuth compounds. It is available commercially. It is th ...
.


See also

* Malonic acid


References

Dicarboxylic acids Deliquescent substances Alpha-keto acids