acetonedicarboxylic acid
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477239490
| Reference = [http://www.sigmaaldrich.com/US/en/product/aldrich/165115 |ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC 1,3-Acetonedicarboxylic acid]{{|bot=InternetArchiveBot |fix-attempted=yes }} at Sigma-Aldrich (safety data sheet)
| ImageFile = Acetonedicarboxylic acid.png
| ImageSize = 180px
| ImageName = Skeletal formula
| ImageFile1 = Acetonedicarboxylic-acid-3D-balls.png
| ImageSize1 = 210px
| ImageName1 = Ball-and-stick model
| PIN = 3-Oxopentanedioic acid
| OtherNames = {{unbulleted list|1,3-Acetonedicarboxylic acid| 3-oxoglutaric acid| 3-ketoglutaric acid| β-ketoglutaric acid}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 61623
| InChI1 = 1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
| InChIKey1 = OXTNCQMOKLOUAM-UHFFFAOYAR
| SMILES1 = O=C(O)CC(=O)CC(=O)O
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =542-05-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = IH7P7WO21P
| PubChem =68328
| ChEBI = 88950
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OXTNCQMOKLOUAM-UHFFFAOYSA-N
| SMILES =C(C(=O)CC(=O)O)C(=O)O
| EINECS = 208-797-9
}}
|Section2={{Chembox Properties
| C=5 | H=6 | O=5
| MolarMass =146.09814 g/mol
| Appearance =
| Density =1.499 g/cm3
| MeltingPtC = 122
| MeltingPt_notes = (decomposes)
| MeltingPt_ref =
| BoilingPtC = 408.4
| BoilingPt_notes =(760mm Hg)
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 214.9
| AutoignitionPtC =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
}}
}}
Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple dicarboxylic acid with the formula {{chem2|O\dC(CH2CO2H)2}}. β-Ketoglutarate does not have the biological activity exhibited by α-ketoglutarate.{{cite journal | vauthors = Bhatkar D, Ananda N, Lokhande KB, Khunteta K, Jain P, Hebale A, Sarode SC, Sharma NK | title = Organic Acids Derived from Saliva-amalgamated Betel Quid Filtrate Are Predicted as a Ten-eleven Translocation-2 Inhibitor | journal = Journal of Cancer Prevention | volume = 28 | issue = 3 | pages = 115–130 | date = September 2023 | pmid = 37830116 | pmc = 10564634 | doi = 10.15430/JCP.2023.28.3.115 | url = }}
Preparation
Acetonedicarboxylic acid can also be prepared by decarboxylation of citric acid in fuming sulfuric acid:{{OrgSynth | author = Roger Adams |author2=H. M. Chiles |author3=C. F. Rassweiler | title = Acetonedicarboxylic Acid | page = 5 | volume = 5 | year = 1925 | doi = 10.15227/orgsyn.005.0005}}
Applications
Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocyclic rings{{Cite book | last1 = Stanovnik | first1 = Branko | last2 = Grošelj | first2 = Uroš
| chapter = Dialkyl Acetone-1,3-Dicarboxylates and their Mono- and bis(Dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems | year = 2010 | title = Advances in Heterocyclic Chemistry Volume 100 | volume = 100 | pages = 145–174 | doi = 10.1016/S0065-2725(10)10005-1| isbn = 9780123809360 }} and in the Weiss–Cook reaction.{{cite journal |doi=10.1021/acs.jchemed.9b00653|title=Process Development of the Weiss–Cook Reaction for the Preparation of cis-1,5-Dimethylbicyclo[3.3.0]octane-3,7-dione in the Undergraduate Organic Laboratory |year=2020 |last1=Korman |first1=Matthew |last2=Paz |first2=Eric |last3=Franklin |first3=Tylor |last4=Lewandowski |first4=Nicholas R. |last5=Sullivan |first5=Bethany |last6=Imhoff |first6=Andrea M. |last7=Fisher |first7=Luke |last8=Bichler |first8=Katherine A. |last9=Van Ornum |first9=Scott G. |journal=Journal of Chemical Education |volume=97 |issue=10 |pages=3835–3838 |bibcode=2020JChEd..97.3835K |s2cid=225248640 }}
Acetonedicarboxylic acid is well known to be used in the Robinson tropinone synthesis.
The presence of β-ketoglutaric acid in human urine is diagnostic for the harmful gut flora such as Candida albicans.Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy