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{{distinguish|Acetylacetone}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 402146017 | verifiedrevid = 446449921
⚫ | Name = Hexane-2,5-dione
| ImageFile_Ref = {{chemboximage|correct|??}} | Name = Hexane-2,5-dione
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Hexane-2,5-dione-2D-skeletal.png | ImageFile = Hexane-2,5-dione-2D-skeletal.png
<!-- | ImageSize = 150px --> <!-- | ImageSize = 150px -->
| ImageName = Skeletal formula of hexane-2,5-dione | ImageName = Skeletal formula of hexane-2,5-dione
⚫ | PIN = Hexane-2,5-dione
| OtherNames = 1,2-diacetylethane<br />'α','β'-diacetylethane<br />acetonyl acetone<br />diacetonyl<br />2,5-dioxohexane<br />2,5-diketohexane<br />2,5-hexanedione | OtherNames = 1,2-Diacetylethane<br />'α','β'-Diacetylethane<br />Acetonyl acetone<br />Diacetonyl<br />2,5-Dioxohexane<br />2,5-Diketohexane<br />2,5-Hexanedione
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| SMILES = O=C(C)CCC(=O)C | SMILES = O=C(C)CCC(=O)C
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7744 | ChemSpiderID = 7744
| PubChem = 8035 | PubChem = 8035
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 85014
| EC_number = 203-738-3
| UNNumber = 1224
| InChI = 1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 | InChI = 1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
| InChIKey = OJVAMHKKJGICOG-UHFFFAOYAH | InChIKey = OJVAMHKKJGICOG-UHFFFAOYAH
Line 20: Line 27:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 110-13-4 | CASNo = 110-13-4
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | RTECS = MO3150000
| UNII = C0Z8884J3P
⚫ | RTECS = MO3150000
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>10</sub>O<sub>2</sub> | Formula = C<sub>6</sub>H<sub>10</sub>O<sub>2</sub>
| MolarMass = 114.1438 g mol<sup>−1</sup> | MolarMass = 114.1438 g mol<sup>−1</sup>
| Appearance = clear, colorless liquid | Appearance = colorless liquid
| Density = 0.973 g cm<sup>−3</sup>, liquid | Density = 0.973 g cm<sup>−3</sup>, liquid
| Solubility = ≥ 10 g/100 ml (22 °C) | Solubility = ≥ 10 g/100 mL (22 °C)
| MagSus = -62.51·10<sup>−6</sup> cm<sup>3</sup>/mol
| MeltingPtC = −5.5
| BoilingPtC = 191.4 | MeltingPtC = −5.5
| Viscosity = | BoilingPtC = 191.4
| Viscosity =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| MolShape = ] at ]<br />] elsewhere | MolShape = ] at ]<br />] elsewhere
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| GHSPictograms = {{GHS07}}{{GHS08}}
| EUClass =
| GHSSignalWord = Warning
| RPhrases =
| HPhrases = {{H-phrases|315|319|373}}
| SPhrases =
| PPhrases = {{P-phrases|260|264|280|302+352|305+351+338|314|321|332+313|337+313|362|501}}
| FlashPt = 78 °C
| Autoignition = | FlashPtC = 78
| AutoignitionPtC =
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| Function = ]s | OtherFunction_label = ]s
| OtherFunctn = ] | OtherFunction = ]
}} }}
}} }}


'''2,5-Hexanedione''' ('''Acetonylacetone''') is an ] ]. It is a colorless liquid.<ref name=OS/> In humans, it is a toxic ] of ] and of ].
'''Hexane-2,5-dione''', ]]], is a ] and a toxic ] of ].


==Symptoms== ==Symptoms of poisoning==
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, ] of the ]s is observed, along with a loss of coordination and problems of vision. 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, ] of the ]s is observed, along with a loss of coordination and vision problems.<ref>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.</ref>


Similar symptoms are observed in animal models. They are associated with a degeneration of the ] (and eventually the ]), starting with the distal portions of the longer and wider nerve ]s. Similar symptoms are observed in animal models. They are associated with a degeneration of the ] (and eventually the ]), starting with the distal portions of the longer and wider nerve ]s.


==Mechanism of action== ==Mechanism of action==
2,5-Hexanedione reacts with ] residues in axonal proteins by ] formation followed by ] to give ]s. ] of the pyrrole residues then causes ]ing and denaturation of proteins, which perturbs axonal transport and function and causes damage to nerve cells.<ref name="ulltox">{{Ullmann| author=Wolfgang Dekant | author2=Spiridon Vamvakas | title=Toxicology | year=2007 | page=23}}</ref>
Hexane-2,5-dione reacts with the ] ]; for example the ] ] of the ] of ] residues in ]s, causing ]ing and a loss of protein function.


==Synthesis==
The ] on the nitrogen attacks either of the ] ] 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 ]. Two water molecules are expelled, creating an ] 2,5-dimethyl] moiety.
2,5-Hexanedione has been prepared in several ways.<ref>http://www.prepchem.com/synthesis-of-2-5-hexanedione/ Primary: Systematic organic chemistry, by W. M. Cumming, 194, 1937.</ref> A common method involves hydrolysis of ], a glucose derived heterocycle.<ref name=OS>{{cite journal|doi=10.15227/orgsyn.016.0025|title=2,5-Dimethylpyrrole|first1=D. M. |last1=Young|first2=C. F. H.|last2=Allen|journal=Organic Syntheses|volume=16|pages=25|year=1936}}</ref>


==Uses==
==Related metabolytes==
Acetonylacetone can be used in the synthesis of ],<ref>{{US patent|2908688}}</ref> ],<ref>{{US patent|4140793}}</ref> and ]. Treatment with ] gives ].
Hexane-2,5-dione can be metabolically dehydrated to ].


==References== ==References==
{{Reflist|30em}}
{{Unreferenced|date=October 2007}}<references/>


] ]

]
]

Latest revision as of 20:31, 17 November 2024

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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