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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:44:38 UTC
Update Date2023-02-21 17:21:07 UTC
HMDB IDHMDB0031648
Secondary Accession Numbers
  • HMDB31648
Metabolite Identification
Common Name2,4-Pentanedione
Description2,4-Pentanedione, also known as 2,4-dioxopentane or ACAC, belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom. Thus, 2,4-pentanedione is considered to be an oxygenated hydrocarbon. 2,4-Pentanedione has been detected, but not quantified in, a few different foods, such as blackberries (Rubus), evergreen blackberries (Rubus laciniatus), and papayas (Carica papaya). This could make 2,4-pentanedione a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2,4-Pentanedione.
Structure
Data?1677000067
Synonyms
ValueSource
2,4-DioxopentaneChEBI
2,4-PentadioneChEBI
ACACChEBI
AcetoacetoneChEBI
Acetyl 2-propanoneChEBI
CH3-CO-CH2-CO-CH3ChEBI
HacacChEBI
Pentan-2,4-dioneChEBI
AcetylacetoneKegg
2,4-PentandioneHMDB
4-Hydroxy-3-penten-2-oneHMDB
Acetyl acetoneHMDB
Acetyl-2-propanoneHMDB
Acetyl-acetoneHMDB
Benzil-related compound, 44HMDB
CH3COCH2COCH3HMDB
DiacetylmethaneHMDB
Pentane-2,4-dioneHMDB
PentanedioneHMDB
Pentanedione-2,4HMDB
Indium-111-acetylacetoneMeSH, HMDB
2,4-PentanedioneChEBI
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Namepentane-2,4-dione
Traditional Nameacetylacetone
CAS Registry Number123-54-6
SMILES
CC(=O)CC(C)=O
InChI Identifier
InChI=1S/C5H8O2/c1-4(6)3-5(2)7/h3H2,1-2H3
InChI KeyYRKCREAYFQTBPV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta-diketones. These are organic compounds containing two keto groups separated by a single carbon atom.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentBeta-diketones
Alternative Parents
Substituents
  • 1,3-diketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-23 °CNot Available
Boiling Point136.00 to 138.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility166 mg/mL at 20 °CNot Available
LogP0.40Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility140 g/LALOGPS
logP-0.2ALOGPS
logP0.33ChemAxon
logS0.15ALOGPS
pKa (Strongest Acidic)8.51ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.09 m³·mol⁻¹ChemAxon
Polarizability10.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+124.89930932474
DeepCCS[M-H]-122.99530932474
DeepCCS[M-2H]-158.71730932474
DeepCCS[M+Na]+133.26830932474
AllCCS[M+H]+123.732859911
AllCCS[M+H-H2O]+119.332859911
AllCCS[M+NH4]+127.832859911
AllCCS[M+Na]+129.032859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-128.732859911
AllCCS[M+HCOO]-132.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,4-PentanedioneCC(=O)CC(C)=O1179.2Standard polar33892256
2,4-PentanedioneCC(=O)CC(C)=O776.8Standard non polar33892256
2,4-PentanedioneCC(=O)CC(C)=O792.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,4-Pentanedione,1TMS,isomer #1CC(=O)C=C(C)O[Si](C)(C)C1050.1Semi standard non polar33892256
2,4-Pentanedione,1TMS,isomer #1CC(=O)C=C(C)O[Si](C)(C)C1003.6Standard non polar33892256
2,4-Pentanedione,1TMS,isomer #2C=C(CC(C)=O)O[Si](C)(C)C1026.4Semi standard non polar33892256
2,4-Pentanedione,1TMS,isomer #2C=C(CC(C)=O)O[Si](C)(C)C1008.1Standard non polar33892256
2,4-Pentanedione,2TMS,isomer #1C=C(C=C(C)O[Si](C)(C)C)O[Si](C)(C)C1198.5Semi standard non polar33892256
2,4-Pentanedione,2TMS,isomer #1C=C(C=C(C)O[Si](C)(C)C)O[Si](C)(C)C1162.2Standard non polar33892256
2,4-Pentanedione,2TMS,isomer #2C=C(CC(=C)O[Si](C)(C)C)O[Si](C)(C)C1165.0Semi standard non polar33892256
2,4-Pentanedione,2TMS,isomer #2C=C(CC(=C)O[Si](C)(C)C)O[Si](C)(C)C1206.0Standard non polar33892256
2,4-Pentanedione,1TBDMS,isomer #1CC(=O)C=C(C)O[Si](C)(C)C(C)(C)C1268.7Semi standard non polar33892256
2,4-Pentanedione,1TBDMS,isomer #1CC(=O)C=C(C)O[Si](C)(C)C(C)(C)C1208.3Standard non polar33892256
2,4-Pentanedione,1TBDMS,isomer #2C=C(CC(C)=O)O[Si](C)(C)C(C)(C)C1225.4Semi standard non polar33892256
2,4-Pentanedione,1TBDMS,isomer #2C=C(CC(C)=O)O[Si](C)(C)C(C)(C)C1203.5Standard non polar33892256
2,4-Pentanedione,2TBDMS,isomer #1C=C(C=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1632.0Semi standard non polar33892256
2,4-Pentanedione,2TBDMS,isomer #1C=C(C=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1610.3Standard non polar33892256
2,4-Pentanedione,2TBDMS,isomer #2C=C(CC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1588.5Semi standard non polar33892256
2,4-Pentanedione,2TBDMS,isomer #2C=C(CC(=C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1610.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-00kf-9100000000-46d8c1174b4626f677532017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9000000000-43699b9ce7635de347062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-000f-9100000000-339a18cfa2c9fef9fc0e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9100000000-f1c22c3e7618740489d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9100000000-bbf09a0b601d6c1b37f42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9100000000-d3295daaa18cb9c248cf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-00kf-9100000000-46d8c1174b4626f677532018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9000000000-43699b9ce7635de347062018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-000f-9100000000-339a18cfa2c9fef9fc0e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9100000000-f1c22c3e7618740489d12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9100000000-bbf09a0b601d6c1b37f42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,4-Pentanedione EI-B (Non-derivatized)splash10-0006-9100000000-d3295daaa18cb9c248cf2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Pentanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-33ab101159a7d4a6d98e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,4-Pentanedione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Positive-QTOFsplash10-0ue9-7900000000-4812cbafad0eb4f8a68b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Positive-QTOFsplash10-0ue9-9500000000-985f6620ed06341c0d7a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Positive-QTOFsplash10-014l-9000000000-926b40c3b86762eb16642016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Negative-QTOFsplash10-0002-9000000000-198e7633acd8394443b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Negative-QTOFsplash10-0002-9000000000-d23c67af0511dd32e26d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Negative-QTOFsplash10-053r-9000000000-ccefb92ad120c18ac6ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Positive-QTOFsplash10-0006-9000000000-c7b1249dbd405b2053902021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Positive-QTOFsplash10-0006-9000000000-afb1c573d3e6ae262efb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Positive-QTOFsplash10-0006-9000000000-96a8981ecdf0987e7d2e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 10V, Negative-QTOFsplash10-0a4i-9000000000-31737175df5f204404122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 20V, Negative-QTOFsplash10-0a4i-9000000000-01cdf05ad77c40eb559b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,4-Pentanedione 40V, Negative-QTOFsplash10-0a4i-9000000000-70ba0c83531aa46f69c52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified23.306 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified6.659 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified16.647 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008303
KNApSAcK IDC00054022
Chemspider ID29001
KEGG Compound IDC15499
BioCyc IDCPD-8879
BiGG IDNot Available
Wikipedia LinkAcetylacetone
METLIN IDNot Available
PubChem Compound31261
PDB IDNot Available
ChEBI ID14750
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1164641
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yuan XH, Liu LM, Ying WB: [Preparation and spectral analysis of Bi(4-x) La(x)Ti3O12 ferroelectric thin films by metal-organic deposition method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Jul;27(7):1355-8. [PubMed:17944413 ]
  2. Li C, Wang S, Huang Y, Zheng B, Tian Z, Wen Y, Li F: Synthesis, characterization and electrochemiluminescent properties of cyclometalated platinum(II) complexes with substituted 2-phenylpyridine ligands. Dalton Trans. 2013 Mar 21;42(11):4059-67. doi: 10.1039/c2dt32466k. Epub 2013 Jan 23. [PubMed:23340796 ]
  3. Rao Ch S, Subash Y E: The effect of chronic tobacco smoking and chewing on the lipid profile. J Clin Diagn Res. 2013 Jan;7(1):31-4. doi: 10.7860/JCDR/2012/5086.2663. Epub 2013 Jan 1. [PubMed:23449989 ]
  4. Yao C, Xu X, Wang J, Shi L, Li L: Low-temperature, solution-processed hole selective layers for polymer solar cells. ACS Appl Mater Interfaces. 2013 Feb;5(3):1100-7. doi: 10.1021/am302878m. Epub 2013 Jan 31. [PubMed:23331483 ]
  5. Muyskens KJ, Alsum JR, Thielke TA, Boer JL, Heetderks TR, Muyskens MA: Photochemistry of UV-excited trifluoroacetylacetone and hexafluoroacetylacetone I: infrared spectra of fluorinated methylfuranones formed by HF photoelimination. J Phys Chem A. 2012 Dec 20;116(50):12305-13. doi: 10.1021/jp307725z. Epub 2012 Dec 6. [PubMed:23176295 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .