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'''Hexane-2,5-dione''' |
'''Hexane-2,5-dione''' is an [[organic compound]] with the formula [[carbon|CH<sub>3</sub>]]COCH2]<sub>2</sub>. It is classified as a [[diketone]]. It is a toxic [[metabolite]] of [[hexane]].<ref>[http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1797843/?report=abstract Carelli et al 2007 ENVIRONMENTAL HEALTH PERSPECTIVES volume 115, pages 113-115]</ref> |
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==Symptoms{ |
==Symptoms{== |
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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 muscle]]s is observed, along with a loss of coordination and problems of vision. |
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 muscle]]s is observed, along with a loss of coordination and problems of vision.<ref>
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.
</ref> |
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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 [[axon]]s. |
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 [[axon]]s. |
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==Mechanism of action== |
==Mechanism of action== |
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Hexane-2,5-dione reacts with the [[amine]] [[ |
Hexane-2,5-dione reacts with the [[amine]]s to give [[pyrrole]]s. Similarly it reacts with the amine [[functional group|group]]s of the [[side chain]] of [[lysine]] residues in [[protein]]s, causing [[cross-link]]ing and a loss of protein function. |
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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%E2%80%93Knorr_synthesis#Pyrrole_synthesis_mechanism|Paal-Knorr pyrrole synthesis]]. Two water molecules are expelled, creating an [[aromaticity|aromatic]] 2,5-dimethyl[[pyrrole]] moiety. Further oxidation of the pyrrole moiety can lead to crosslinking.<ref>[http://www.tandfonline.com/doi/abs/10.1080/15287390902959508 LoPachin et al 2009 Journal of Toxicology and Environmental Health, Part A volume 72, pages 861-869]</ref> |
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%E2%80%93Knorr_synthesis#Pyrrole_synthesis_mechanism|Paal-Knorr pyrrole synthesis]]. Two water molecules are expelled, creating an [[aromaticity|aromatic]] 2,5-dimethyl[[pyrrole]] moiety. Further oxidation of the pyrrole moiety can lead to crosslinking.<ref>[http://www.tandfonline.com/doi/abs/10.1080/15287390902959508 LoPachin et al 2009 Journal of Toxicology and Environmental Health, Part A volume 72, pages 861-869]</ref> |
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==Related metabolytes== |
==Related metabolytes== |
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Hexane-2,5-dione can be |
Hexane-2,5-dione can be dehydrated to [[2,5-dimethylfuran]]. |
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==References== |
==References== |
Revision as of 18:09, 25 November 2013
Names | |
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Other names
1,2-diacetylethane
'α','β'-diacetylethane acetonyl acetone diacetonyl 2,5-dioxohexane 2,5-diketohexane 2,5-hexanedione | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.003.400 |
PubChem CID
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RTECS number |
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CompTox Dashboard (EPA)
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Properties | |
C6H10O2 | |
Molar mass | 114.1438 g mol−1 |
Appearance | clear, colorless liquid |
Density | 0.973 g cm−3, liquid |
Melting point | −5.5 °C (22.1 °F; 267.6 K) |
Boiling point | 191.4 °C (376.5 °F; 464.5 K) |
≥ 10 g/100 ml (22 °C) | |
Structure | |
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 [77 °F], 100 kPa).
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Hexane-2,5-dione is an organic compound with the formula CH3COCH2]2. It is classified as a diketone. It is a toxic metabolite of hexane.[1]
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.[2]
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.[3]
Related metabolytes
Hexane-2,5-dione can be dehydrated to 2,5-dimethylfuran.
References
- ^ 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