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Hexane-2,5-dione

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Hexane-2,5-dione
Skeletal formula of hexane-2,5-dione
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 Edit this at Wikidata
PubChem CID
RTECS number
  • MO3150000
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3Key: OJVAMHKKJGICOG-UHFFFAOYSA-N
  • InChI=1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3Key: OJVAMHKKJGICOG-UHFFFAOYAH
SMILES
  • O=C(C)CCC(=O)C
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). checkY verify (what is  ?) Infobox references
Chemical compound

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, joining the chain, and again protonating the oxygen and deprotonating the nitrogen. Two water molecules are then lost from the system, creating aromaticity: 2,5-dimethylpyrrole.

Related metabolytes

Hexane-2,5-dione can be metabolically dehydrated to 2,5-dimethylfuran.

References

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