Glyoxalic acid
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| Names | |
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Preferred IUPAC name
Oxoacetic acid
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Systematic IUPAC name
Oxoethanoic acid
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| Other names
Glyoxylic acid
2-Oxoacetic acid Formylformic acid |
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
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| DrugBank | |
| ECHA InfoCard | 100.005.508 |
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PubChem CID
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| Properties | |
| C2H2O3 | |
| Molar mass | 74.04 g·mol−1 |
| Density | 1.384 g/mL |
| Melting point | 80 °C (176 °F; 353 K) |
| Boiling point | 111 °C (232 °F; 384 K) |
| Acidity (pKa) | 3.18, 3.32 |
| Related compounds | |
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Other anions
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glyoxylate |
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Related carboxylic acids
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formic acid acetic acid glycolic acid oxalic acid propionic acid pyruvic acid |
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Related compounds
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acetaldehyde glyoxal glycolaldehyde |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially.
Glyoxylic acid is usually described with the chemical formula OCHCO2H, i.e. containing an aldehyde functional group (see image in upper right). The aldehyde in fact is not observed in solution or as a solid. As seen for many other aldehydes, it exists most commonly as the hydrate. Thus, the formula for glyoxylic acid is really (HO)2CHCO2H, described as the "monohydrate." This geminal diol exists in equilibrium with the dimeric hemiacetal in solution: Henry's law constant of glyoxylic acid is KH = 1.09 × 104 × exp[(40.0 × 103/R) × (1/T − 1/298)].
The compound is formed by organic oxidation of glyoxal with hot nitric acid, the main side product being oxalic acid. However, this reaction is highly exothermic and prone to thermal runaway.
Ozonolysis of maleic acid is also effective.
Historically glyoxylic acid was prepared from oxalic acid electrosynthetically:
In organic synthesis, lead dioxide anodes were applied for the production of glyoxylic acid from oxalic acid in a sulfuric acid electrolyte.
The conjugate base of glyoxylic acid is known as glyoxylate and is the form that the compound exists in solution at neutral pH. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides.
Glyoxylate is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi, and plants to convert fatty acids into carbohydrates. The glyoxylate cycle is also important for induction of plant defense mechanisms in response to fungi. The glyoxylate cycle is initiated through the activity of isocitrate lyase, which converts isocitrate into glyoxylate and succinate. Research is being done to co-opt the pathway for a variety of uses such as the biosynthesis of succinate.
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Wikipedia