Hexane-2,5-dione
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| Hexane-2,5-dione | |
|---|---|
| Image:Hexane-2,5-dione-2D-skeletal.png | |
| General | |
| Other names | 1,2-diacetylethane 'α','β'-diacetylethane acetonyl acetone diacetonyl 2,5-dioxohexane 2,5-diketohexane 2,5-hexanedione |
| Molecular formula | C6H10O2 |
| SMILES | CC(=O)CCC(=O)C |
| Molar mass | 114.1438 g mol−1 |
| Appearance | clear, colorless liquid |
| CAS number | [110-13-4] |
| Properties | |
| Density and phase | 0.973 g cm−3, liquid |
| Solubility in water | ≥ 10 g/100 ml (22 °C) |
| Melting point | −5.5 °C (267.7 K) |
| Boiling point | 191 °C (464 K) |
| Viscosity | ? cP at ? °C |
| Structure | |
| Molecular shape | trigonal planar at carbonyl tetrahedral elsewhere |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| EU classification | ? |
| NFPA 704 | ? |
| R-phrases | ? |
| S-phrases | ? |
| Flash point | 78 °C |
| Autoignition temperature | ? |
| RTECS number | MO3150000 |
| Supplementary data page | |
| Structure and properties | n, εr, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related diketones | acetylacetone |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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, losing hydrogen and protonating the oxygen. The Nitrogen is now attached to the 2 position of the chain; its lone pair again attacks the carbon of the other carbonyl. Again joining the chain, protonating the oxygen and deprotonating the nitrogen. Two water molecules are then lost from the system, creating aromaticity: 2,5-dimethlypyrrole.
Related metabolytes
Hexane-2,5-dione can be metabolically dehydrated to 2,5-dimethylfuran.lv:Acetonilacetons
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
