Hexane-2,5-dione: Difference between revisions

{{distinguish|Acetylacetone}}

| Verifiedfields = changed

| verifiedrevid = 446449921

| Name = Hexane-2,5-dione

| ImageFile_Ref = {{chemboximage|correct|??}}

| 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

|Section1={{Chembox Identifiers

| SMILES = O=C(C)CCC(=O)C

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 85014

| EC_number = 203-738-3

| UNNumber = 1224

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = C0Z8884J3P

| RTECS = MO3150000

|Section2={{Chembox Properties

| Formula = C₆H₁₀O₂

| MolarMass = 114.1438 g mol⁻¹

| Appearance = colorless liquid

| Density = 0.973 g cm⁻³, liquid

| Solubility = ≥ 10 g/100 mL (22 °C)

| MagSus = -62.51·10⁻⁶ cm³/mol

| MeltingPtC = −5.5

| BoilingPtC = 191.4

| Viscosity =

|Section3={{Chembox Structure

| MolShape = [[trigonal planar]] at [[carbonyl]]<br />[[tetrahedral molecular geometry|tetrahedral]] elsewhere

| Dipole =

|Section7={{Chembox Hazards

| ExternalSDS =

| GHSPictograms = {{GHS07}}{{GHS08}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|373}}

| PPhrases = {{P-phrases|260|264|280|302+352|305+351+338|314|321|332+313|337+313|362|501}}

| FlashPtC = 78

| AutoignitionPtC =

|Section8={{Chembox Related

| OtherFunction_label = [[diketone]]s

| OtherFunction = [[acetylacetone]]

'''2,5-Hexanedione''' ('''Acetonylacetone''') is an [[aliphatic]] [[diketone]]. It is a colorless liquid.<ref name=OS/> 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 muscle]]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>

It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-diketone structure since [[2,3-hexanedione|2,3-]], [[2,4-hexanedione]] and [[2,6-heptanedione]] are not neurotoxic, whereas [[2,5-heptanedione]] and [[3,6-octanedione]] and other γ-diketones are.<ref name="tox">{{citation | author=Stephen R Clough | author2=Leyna Mulholland | contribution=Hexane | title=Encyclopedia of Toxicology | volume=2 | edition=2nd | year=2005 | publisher=Elsevier | pages=522–525}}</ref>

2,5-Hexanedione reacts with [[lysine]] residues in axonal proteins by [[Schiff base]] formation followed by [[cyclization]] to give [[pyrrole]]s. [[Oxidation]] of the pyrrole residues then causes [[cross-link]]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>

==Synthesis==

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 [[2,5-Dimethylfuran|2,5-dimethylfuran]], 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==

Acetonylacetone can be used in the synthesis of [[isocarboxazid]],<ref>{{US patent|2908688}}</ref> [[rolgamidine]],<ref>{{US patent|4140793}}</ref> and [[mopidralazine]]. Treatment with [[Phosphorus pentasulfide|P₄S₁₀]] gives [[2,5-Dimethylthiophene|2,5-dimethylthiophene]].

==References==

{{Reflist|30em}}

[[Category:Diketones]]