Record Information
Version2.0
Creation Date2012-05-31 09:56:23 -0600
Update Date2015-10-02 02:25:48 -0600
Secondary Accession Numbers
  • ECMDB00060
Identification
Name:Acetoacetic acid
Description:Acetoacetic acid is a member of the chemical class known as Beta Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C3 carbon atom. Acetoacetic acid (also called diacetic acid) is the organic compound with the formula CH3C(O)CH2CO2H. It is the simplest beta-keto acid group and like other members of this class is unstable. (WikiPedia)
Structure
Thumb
Synonyms:
  • β-ketobutyrate
  • β-ketobutyric acid
  • 3-Ketobutyrate
  • 3-Ketobutyric acid
  • 3-Oxo-butanoate
  • 3-Oxo-butanoic acid
  • 3-Oxobutanate
  • 3-Oxobutanic acid
  • 3-Oxobutanoate
  • 3-Oxobutanoic acid
  • 3-Oxobutyrate
  • 3-Oxobutyric acid
  • a-Ketobutyrate
  • a-Ketobutyric acid
  • Acetoacetate
  • Acetoacetic acid
  • Alpha-Ketobutyrate
  • Alpha-Ketobutyric acid
  • b-Ketobutyrate
  • b-Ketobutyric acid
  • Beta-Ketobutyrate
  • Beta-Ketobutyric acid
  • Diacetate
  • Diacetic acid
  • Oxobutyrate
  • Oxobutyric acid
  • α-Ketobutyrate
  • α-Ketobutyric acid
  • β-Ketobutyrate
  • β-Ketobutyric acid
Chemical Formula:C4H6O3
Weight:Average: 102.0886
Monoisotopic: 102.031694058
InChI Key:WDJHALXBUFZDSR-UHFFFAOYSA-N
InChI:InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)
CAS number:541-50-4
IUPAC Name:3-oxobutanoic acid
Traditional IUPAC Name:acetoacetic acid
SMILES:CC(=O)CC(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Beta-keto acid
  • 1,3-dicarbonyl compound
  • Beta-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:36.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/ml [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-0.416PhysProp
Predicted Properties
PropertyValueSource
Water Solubility240.0 mg/mLALOGPS
logP-0.47ALOGPS
logP-0.0015ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.54 m3·mol-1ChemAxon
Polarizability9.18 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Acetate metabolismPW002090 Pw002090Pw002090 greyscalePw002090 simple
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
37± 9 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kk-3940000000-008eb78d2ba3cfa053b4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9500000000-c3940e591f8aef9d6aacView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9800000000-67a95675672c3f5447a7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-1778836b3908a79b814fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4950000000-4039bb48c98ec17b5c0cView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-000i-9200000000-9b4ab7b6a41632cb125bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0udi-6900000000-cfab9d4cdb56acafe8ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0pb9-9800000000-108aa5ef93455fb1ba28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. Pubmed: 6321058
  • de Araujo Burgos MG, Bion FM, Campos F: [Lactation and alcohol: clinical and nutritional effects] Arch Latinoam Nutr. 2004 Mar;54(1):25-35. Pubmed: 15332353
  • Fritzsche I, Buhrdel P, Melcher R, Bohme HJ: Stability of ketone bodies in serum in dependence on storage time and storage temperature. Clin Lab. 2001;47(7-8):399-403. Pubmed: 11499803
  • Fulop M, Murthy V, Michilli A, Nalamati J, Qian Q, Saitowitz A: Serum beta-hydroxybutyrate measurement in patients with uncontrolled diabetes mellitus. Arch Intern Med. 1999 Feb 22;159(4):381-4. Pubmed: 10030312
  • Galey JB, Destree O, Dumats J, Genard S, Tachon P: Protection against oxidative damage by iron chelators: effect of lipophilic analogues and prodrugs of N,N'-bis(3,4,5-trimethoxybenzyl)ethylenediamine- N,N'-diacetic acid (OR10141). J Med Chem. 2000 Apr 6;43(7):1418-21. Pubmed: 10753479
  • Heller MJ, Adams PW, Orosz CG: Evaluation of an automated method of percent reactive antibody determination. Hum Immunol. 1992 Nov;35(3):179-87. Pubmed: 1293081
  • Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Krejsa CM, Schieven GL: Detection of oxidative stress in lymphocytes using dichlorodihydrofluorescein diacetate. Methods Mol Biol. 2000;99:35-47. Pubmed: 10909075
  • Mahowald ML, Handwerger BS, Capertone EM Jr, Douglas SD: A comparative study of procedures for sheep erythrocyte-human-T-lymphocyte rosette formation. J Immunol Methods. 1977;15(3):239-45. Pubmed: 404361
  • Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. Pubmed: 7762816
  • Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. Pubmed: 6696735
  • Oligny LL, Lough J: Hepatic sinusoidal ectasia. Hum Pathol. 1992 Aug;23(8):953-6. Pubmed: 1644440
  • Polsky-Fisher SL, Cao H, Lu P, Gibson CR: Effect of cytochromes P450 chemical inhibitors and monoclonal antibodies on human liver microsomal esterase activity. Drug Metab Dispos. 2006 Aug;34(8):1361-6. Epub 2006 May 23. Pubmed: 16720683
  • Saibara T, Onishi S, Sone J, Yamamoto N, Shimahara Y, Mori K, Ozawa K, Yamamoto Y: Arterial ketone body ratio as a possible indicator for liver transplantation in fulminant hepatic failure. Transplantation. 1991 Apr;51(4):782-6. Pubmed: 2014530
  • Sato T, Oouchi M, Nagakubo H, Chiba T, Ogawa S, Sato C, Sugimura K, Fukuda M: Effect of pravastatin on plasma ketone bodies in diabetics with hypercholesterolemia. Tohoku J Exp Med. 1998 May;185(1):25-9. Pubmed: 9710942
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  • Tanaka Y, Ohdan H, Onoe T, Mitsuta H, Tashiro H, Itamoto T, Asahara T: Low incidence of acute rejection after living-donor liver transplantation: immunologic analyses by mixed lymphocyte reaction using a carboxyfluorescein diacetate succinimidyl ester labeling technique. Transplantation. 2005 May 15;79(9):1262-7. Pubmed: 15880082
  • Tasker RC, Lutman D, Peters MJ: Hyperventilation in severe diabetic ketoacidosis. Pediatr Crit Care Med. 2005 Jul;6(4):405-11. Pubmed: 15982426
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Walker V, Mills GA, Mellor JM, Langley GJ, Farrant RD: A novel pyrroline-5-carboxylic acid and acetoacetic acid adduct in hyperprolinaemia type II. Clin Chim Acta. 2003 May;331(1-2):7-17. Pubmed: 12691858
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yeh YY, Sheehan PM: Preferential utilization of ketone bodies in the brain and lung of newborn rats. Fed Proc. 1985 Apr;44(7):2352-8. Pubmed: 3884391
  • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834
Synthesis Reference:Lopez-Soriano, F. J.; Argiles, J. M. A simple method for the preparation of acetoacetate. Analytical Letters (1985), 18(B5), 589-92.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15344
HMDB IDHMDB00060
Pubchem Compound ID96
Kegg IDC00164
ChemSpider ID94
WikipediaAcetoacetic acid
BioCyc ID3-KETOBUTYRATE
EcoCyc ID3-KETOBUTYRATE
Ligand ExpoLIN

Enzymes

General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoD
Uniprot ID:
P76458
Molecular weight:
23526
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoA
Uniprot ID:
P76459
Molecular weight:
22960
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.

Transporters

General function:
Lipid transport and metabolism
Specific function:
Responsible for the intake of short-chain fatty acids
Gene Name:
atoE
Uniprot ID:
P76460
Molecular weight:
47527
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368