CH3COCHO

CH3COCHO is methylglyoxal, an organic compound with the chemical formula C3H4O2. It is an α-dicarbonyl compound containing both an aldehyde and a ketone, with IUPAC name 2-oxopropanal and synonyms including methylglyoxal and pyruvaldehyde.

Structural and chemical description: The molecule consists of a three-carbon chain with a terminal aldehyde group (−CHO) and a ketone (−CO−) at the middle carbon, giving the arrangement CH3–CO–CHO. This arrangement makes it a highly reactive carbonyl compound.

Occurrence and biosynthesis: Methylglyoxal is produced endogenously as a byproduct of metabolism, particularly glycolysis. It can form spontaneously from triose phosphates such as glyceraldehyde-3-phosphate and dihydroxyacetone phosphate, and in some microorganisms from dihydroxyacetone phosphate via methylglyoxal synthase. In cells, it is detoxified by the glyoxalase system, which uses glutathione to convert it to D-lactate.

Properties: It is highly reactive due to its adjacent carbonyl groups. In aqueous solutions it rapidly hydrates to the corresponding diol, and the anhydrous form is unstable. It is miscible with water and widely used as a reactive intermediate in various chemical contexts.

Reactions and applications: Methylglyoxal readily forms advanced glycation end products with proteins and nucleic acids, a property exploited in biochemical research as a model glycating agent and in studies of carbonyl stress and detoxification pathways. It also serves as a chemical intermediate in organic synthesis.

Safety: It is toxic and potentially mutagenic; it can irritate skin, eyes, and mucous membranes. Proper handling, ventilation, and storage are required due to its reactive nature.