|Jmol-3D images||Image 1|
|Molar mass||114.1438 g mol−1|
|Density||0.973 g cm−3, liquid|
−5.5 °C, 268 K, 22 °F
191.4 °C, 465 K, 377 °F
|Solubility in water||≥ 10 g/100 mL (22 °C)|
|Molecular shape||trigonal planar at carbonyl
|Flash point||78 °C|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
The initial symptoms of chronic hexane toxicity, attributable to hexane-2,5-dione, 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
Hexane-2,5-dione reacts with the amines to give pyrroles. Similarly it reacts with the amine groups of the side chain of lysine residues in proteins, causing cross-linking and a loss of protein function.
The lone pair on the nitrogen attacks either of the electron deficient carbonyl carbons, forming a tetrahedral hemiaminal intermediate. A heterocyclic structure is formed as the second carbonyl carbon is attacked and a 2,5-dihydroxytetrafuran forms, akin to the Paal-Knorr pyrrole synthesis. Two water molecules are expelled, creating an aromatic 2,5-dimethylpyrrole moiety. Further oxidation of the pyrrole moiety can lead to crosslinking.
Hexane-2,5-dione can be dehydrated to 2,5-dimethylfuran.
- Carelli et al 2007 ENVIRONMENTAL HEALTH PERSPECTIVES volume 115, pages 113-115
- Couri D, Milks M. "Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione" Annual Rev. Pharmacol. Toxicol. 1982;22:145-66.
- LoPachin et al 2009 Journal of Toxicology and Environmental Health, Part A volume 72, pages 861-869