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Revision as of 14:21, 13 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit Latest revision as of 20:31, 17 November 2024 edit undoMrLinkinPark333 (talk | contribs)Autopatrolled, Extended confirmed users78,866 edits remove copying of https://www.google.ca/books/edition/Encyclopedia_of_Toxicology/h3dqAAAAMAAJ?hl=en&gbpv=1&printsec=frontcover&bsq=%22hexanedione%20resides%22 page 523 
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{{distinguish|Acetylacetone}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 390296240 | verifiedrevid = 446449921
⚫ | Name = Hexane-2,5-dione
| ImageFile = Hexane-2,5-dione-2D-skeletal.png | Name = Hexane-2,5-dione
| ImageFile_Ref = {{chemboximage|correct|??}}
| 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 = 7744
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 | StdInChI = 1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OJVAMHKKJGICOG-UHFFFAOYSA-N | StdInChIKey = OJVAMHKKJGICOG-UHFFFAOYSA-N
| 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, losing hydrogen and protonating the oxygen. The Nitrogen is now attached to the 2 position of the chain; its lone pair again attacks the carbon of the other carbonyl, joining the chain, and again protonating the oxygen and deprotonating the nitrogen. Two water molecules are then lost from the system, creating ]: 2,5-dimethyl].
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/>


] ]

]