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 Y
PubChem	8035
ChemSpider	7744 Y
RTECS number	MO3150000
Jmol-3D images	Image 1
SMILES O=C(C)CCC(=O)C
InChI InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Y Key: OJVAMHKKJGICOG-UHFFFAOYSA-N Y InChI=1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Key: OJVAMHKKJGICOG-UHFFFAOYAH
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, 268 K, 22 °F
Boiling point	191.4 °C, 465 K, 377 °F
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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, 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.

Related metabolytes

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

References