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Hexane-2,5-dione

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(Redirected from 2,5-Hexanedione) Not to be confused with Acetylacetone.
Hexane-2,5-dione
Skeletal formula of hexane-2,5-dione
Names
Preferred IUPAC name 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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.400 Edit this at Wikidata
EC Number
  • 203-738-3
PubChem CID
RTECS number
  • MO3150000
UNII
UN number 1224
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 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)
Magnetic susceptibility (χ) -62.51·10 cm/mol
Structure
Molecular shape trigonal planar at carbonyl
tetrahedral elsewhere
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazard
Signal word Warning
Hazard statements H315, H319, H373
Precautionary statements P260, P264, P280, P302+P352, P305+P351+P338, P314, P321, P332+P313, P337+P313, P362, P501
Flash point 78 °C (172 °F; 351 K)
Related compounds
Related diketones acetylacetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid. In humans, it is a toxic metabolite of hexane and of 2-hexanone.

Symptoms of poisoning

The chronic toxicity of hexane is attributed to hexane-2,5-dione. The symptoms 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 vision problems.

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

2,5-Hexanedione reacts with lysine residues in axonal proteins by Schiff base formation followed by cyclization to give pyrroles. Oxidation of the pyrrole residues then causes cross-linking and denaturation of proteins, which perturbs axonal transport and function and causes damage to nerve cells.

Synthesis

2,5-Hexanedione has been prepared in several ways. A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle.

Uses

Acetonylacetone can be used in the synthesis of isocarboxazid, rolgamidine, and mopidralazine. Treatment with P4S10 gives 2,5-dimethylthiophene.

References

  1. ^ Young, D. M.; Allen, C. F. H. (1936). "2,5-Dimethylpyrrole". Organic Syntheses. 16: 25. doi:10.15227/orgsyn.016.0025.
  2. Couri D, Milks M. "Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione" Annu. Rev. Pharmacol. Toxicol. 1982;22:145-66.
  3. Wolfgang Dekant; Spiridon Vamvakas (2007). "Toxicology". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 23. ISBN 978-3527306732.
  4. http://www.prepchem.com/synthesis-of-2-5-hexanedione/ Primary: Systematic organic chemistry, by W. M. Cumming, 194, 1937.
  5. U.S. patent 2,908,688
  6. U.S. patent 4,140,793
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