Methylglyoxal
From Wikipedia, the free encyclopedia
| Methylglyoxal | |
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| Chemical name | Methylglyoxal |
| Chemical formula | C3H4O2 |
| Molecular mass | 72.06 g/mol |
| CAS number | [78-98-8] |
| Density | x.xxx g/cm3 |
| Melting point | xx.x °C |
| Boiling point | xx.x °C |
| SMILES | xxx |
| Disclaimer and references | |
Methylglyoxal, also called pyruvaldehyde or 2-oxo-propanal (CH3-CO-CH=O or C3H4O2) is the aldehyde form of pyruvic acid. It has two carbonyl groups, so it is a dicarbonyl compound. Methylglyoxal is both an aldehyde and a ketone. In the body, methylglyoxal may form from 3-amino acetone, which is an intermediate of threonine catabolism. This compound, as well as glyoxal, is a byproduct of metabolism, but cannot be used. The aldehyde reacts with glutathione, a tripeptide consisting of glutamic acid, cysteine, and glycine. Glutathione reduces methylglyoxal to 1-hydroxy acetone, a ketol. 1-Hydroxy acetone goes through enediol tautomerism to lactaldehyde. Then the lactaldehyde is oxidised by glutathione to D-lactic acid. Methylglyoxal is also called a ketal, because it has an aldehydic and ketonic carbonyl group. It is a type of the advanced glycation endproducts(AGEs) resulting from sugar modifications, such as the Maillard reaction. When the reductone is cleaved, pyruvaldehyde forms. There are 4 main glycation sugars:
- Glucose, the sugar that stores energy
- Galactose, a part of milk sugar (lactose)
- Allose, an all-cis hexose carried into the cell by special proteins
- Ribose, a component of RNA
