Formula C6H10O2 Density 973 kg/m³ | Molar mass 114.1438 g/mol Appearance colorless liquid | |
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2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. In human, it is a toxic metabolite of hexane and of 2-hexanone.
Contents
Symptoms of poisoning
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 problems of vision.
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.
Mechanism of action
It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-diketone structure since 2,3-, 2,4-hexanedione and 2,6-heptanedione are not neurotoxic, while 2,5-heptanedione and 3,6-octanedione and other γ-diketones are neurotoxic. In fact, higher α-diketones, like 2,3-pentanedione and 2,3-hexanedione, are found in small amounts in various foods. They are used as aroma components in alcohol-free beverages and in baked goods.
2,5-Hexanedione reacts with critical lysine residues in axonal proteins by Schiff base formation followed by cyclization to give pyrroles. Oxidation of the pyrrole residues then causes cross-linking between two n-hexane-modified proteins. The resulting denaturation of proteins perturbs axonal transport and function and causes damage to nerve cells.
Synthesis
A Process for preparing 2,5-hexanedione has been described:
Uses
Acetonylacetone can be used in the synthesis of isocarboxazid, rolgamidine, and mopidralazine.