| Hexane-2,5-dione | |
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Other names
1,2-diacetylethane |
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| Identifiers | |
| CAS number | 110-13-4 |
| PubChem | 8035 |
| ChemSpider | 7744 |
| RTECS number | MO3150000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C6H10O2 |
| Molar mass | 114.1438 g mol−1 |
| Appearance | clear, colorless liquid |
| Density | 0.973 g cm−3, liquid |
| Melting point |
−5.5 °C, 268 K, 22 °F |
| Boiling point |
191.4 °C, 465 K, 377 °F |
| Solubility in water | ≥ 10 g/100 ml (22 °C) |
| Structure | |
| Molecular shape | trigonal planar at carbonyl tetrahedral elsewhere |
| Hazards | |
| Flash point | 78 °C |
| Related compounds | |
| Related diketones | acetylacetone |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Hexane-2,5-dione, C6H10O2, is a diketone and a toxic metabolite of hexane.
Contents |
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.
Hexane-2,5-dione reacts with the amine functional group; for example the amine group 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.
Hexane-2,5-dione can be metabolically dehydrated to 2,5-dimethylfuran.