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Glyoxylic acid

Glyoxylic acid

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.

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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

^ 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.
^ 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.