Hexane-2,5-dione

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Hexane-2,5-dione
Skeletal formula of hexane-2,5-dione Hexane-2,5-dione-2D-skeletal.png
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.400 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-738-3
PubChem CID
RTECS number
  • MO3150000
UNII
UN number 1224
  • InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Yes check.svgY
    Key: OJVAMHKKJGICOG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
    Key: OJVAMHKKJGICOG-UHFFFAOYAH
  • O=C(C)CCC(=O)C
Properties
C6H10O2
Molar mass 114.1438 g mol−1
Appearancecolorless liquid
Density 0.973 g cm−3, liquid
Melting point −5.5 °C (22.1 °F; 267.6 K)
Boiling point 191.4 °C (376.5 °F; 464.5 K)
≥ 10 g/100 mL (22 °C)
−62.51·10−6 cm3/mol
Structure
trigonal planar at carbonyl
tetrahedral elsewhere
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Warning
H315, H319, H373
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 [77 °F], 100 kPa).
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2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid. [1] In humans, it is a toxic metabolite of hexane and of 2-hexanone.

Contents

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. [2]

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. [3]

Synthesis

2,5-Hexanedione has been prepared in several ways. [4] A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle. [1]

Uses

Acetonylacetone can be used in the synthesis of isocarboxazid, [5] rolgamidine, [6] and mopidralazine. Treatment with P4S10 gives 2,5-dimethylthiophene.

References

  1. 1 2 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   978-3-527-30673-2.
  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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