Hexane-2,5-dione should not be confused with Acetylacetone.
2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid. In humans, it is a toxic metabolite of hexane and of 2-hexanone.
The chronic toxicity of hexane is attributed to hexane-2,5-dione. The symptoms are tingling and cramps in the arms and legs, followed by general muscular weakness. In severe cases, atrophy of the skeletal muscles is observed, along with a loss of coordination and vision problems.[1]
Similar symptoms are observed in animal models. They are associated with a degeneration of the peripheral nervous system (and eventually the central nervous system), starting with the distal portions of the longer and wider nerve axons.
2,5-Hexanedione reacts with lysine residues in axonal proteins by Schiff base formation followed by cyclization to give pyrroles. Oxidation of the pyrrole residues then causes cross-linking and denaturation of proteins, which perturbs axonal transport and function and causes damage to nerve cells.
2,5-Hexanedione has been prepared in several ways.[2] A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle.[3]
Acetonylacetone can be used in the synthesis of isocarboxazid, rolgamidine, and mopidralazine. Treatment with P4S10 gives 2,5-dimethylthiophene.