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| Names | |
|---|---|
| Other names
1,2-diacetylethane 'α','β'-diacetylethane acetonyl acetone diacetonyl 2,5-dioxohexane 2,5-diketohexane 2,5-hexanedione | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.003.400 
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| PubChem CID | |
| RTECS number |
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| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C6H10O2 |
| Molar mass | 114.1438 g mol |
| Appearance | clear, colorless liquid |
| Density | 0.973 g cm, liquid |
| Melting point | −5.5 °C (22.1 °F; 267.6 K) |
| Boiling point | 191.4 °C (376.5 °F; 464.5 K) |
| 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 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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Hexane-2,5-dione, C6H10O2, is a diketone and a toxic metabolite of hexane.
Symptoms
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 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.
Related metabolytes
Hexane-2,5-dione can be metabolically dehydrated to 2,5-dimethylfuran.
References
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