Mesoxalic acid

Mesoxalic acid[1]
Structural formula
Ball-and-stick model
Names
Preferred IUPAC name
Oxopropanedioic acid
Other names
Ketomalonic acid
Oxomalonic acid
α-Ketomalonic acid
2-Oxopropanedioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.006.796 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8) checkY
    Key: XEEVLJKYYUVTRC-UHFFFAOYSA-N checkY
  • InChI=1/C3H2O5/c4-1(2(5)6)3(7)8/h(H,5,6)(H,7,8)
    Key: XEEVLJKYYUVTRC-UHFFFAOYAW
  • O=C(O)C(=O)C(=O)O
Properties
C3H2O5
Molar mass 118.045 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Mesoxalic acid, also called oxomalonic acid or ketomalonic acid, is an organic compound with formula C3H2O5 or HO−(C=O)3−OH.

Mesoxalic acid is both a dicarboxylic acid and a ketonic acid. It readily loses two protons to yield the divalent anion C3O2−5, called mesoxalate, oxomalonate, or ketomalonate. These terms are also used for salts containing this anion, such as sodium mesoxalate, Na2C3O5; and for esters containing the −C3O5− or −O−(C=O)3−O− moiety, such as diethyl mesoxalate, (C2H5)2C3O5. Mesoxalate is one of the oxocarbon anions, which (like carbonate CO2−3 and oxalate C2O2−4) consist solely of carbon and oxygen.

Mesoxalic acid readily absorbs and reacts with water to form a product commonly called "mesoxalic acid monohydrate", more properly dihydroxymalonic acid, HO−(C=O)−C(OH)2−(C=O)−OH.[2] 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.

  1. ^ Merck Index (12th ed.). p. 5971.
  2. ^ Cite error: The named reference roscoe was invoked but never defined (see the help page).