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Hexane-2,5-dione



Hexane-2,5-dione
Other names 1,2-diacetylethane
'α','β'-diacetylethane
acetonyl acetone
diacetonyl
2,5-dioxohexane
2,5-diketohexane
2,5-hexanedione
Identifiers
CAS number 110-13-4
RTECS number MO3150000
SMILES CC(=O)CCC(=O)C
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 (267.7 K)

Boiling point

191 °C (464 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
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.

Contents

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.

References
     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Hexane-2,5-dione". A list of authors is available in Wikipedia.
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