Glyoxylic acid

Glyoxylic acid
IUPAC name	oxoethanoic acid
Other names	formylformic acid; oxoethanoic acid
Identifiers
CAS number	[298-12-4]
SMILES	O=CC(O)=O
ChemSpider ID	740
Properties
Molecular formula	C2H2O3
Molar mass	74.04 g/mol
Density	g/cm3
Melting point	−93 °C
Boiling point	111 °C
Related compounds
Other anions	glyoxylate
Related carboxylic acids	formic acid acetic acid glycolic acid oxalic acid propionic acid pyruvic acid
Related compounds	acetaldehyde glyoxal glycolaldehyde
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

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

Glyoxylic acid 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 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.

The conjugate base of gloxylic acid is known as 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.