Glyoxylic acid

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Glyoxylic acid
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IUPAC name oxoethanoic acid
Other names formylformic acid
Identifiers
CAS number 563-96-2
SMILES O=CC(O)=O
Properties
Molecular formula C2H2O3
Molar mass 74.04 g mol-1
Density g cm-3
Melting point

-93 °C

Boiling point

111 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Glyoxylic acid or oxoacetic acid is an organic compound with the chemical formula C2H2O3.

Other synonyms are formylformic acid and oxoethanoic acid. The compound is an aldehyde and a carboxylic acid. Alkyl esters of glyoxylic acid are called alkyl glyoxylic acids. The compound is formed by organic oxidation of glycolic acid or ozonolysis of maleic acid. Glyoxylic acid is a liquid with a melting point of -93 °C and a boiling point of 111 °C. It is available commercially as a monohydrate or as a solution in water.

When the carboxyl group of glyoxylic acid loses a proton it turns into glyoxylate. This compound is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, [1] fungi, and plants [2] to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.

References

  1. Holms WH (1987). "Control of flux through the citric acid cycle and the glyoxylate bypass in Escherichia coli". Biochem Soc Symp. 54: 17–31. PMID 3332993. 
  2. Escher CL, Widmer F (1997). "Lipid mobilization and gluconeogenesis in plants: do glyoxylate cycle enzyme activities constitute a real cycle? A hypothesis". Biol Chem. 378: 803–813. PMID 9377475. 
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