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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, forming a tetrahedral 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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