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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:44:16 UTC
Update Date2022-03-07 02:53:02 UTC
HMDB IDHMDB0031598
Secondary Accession Numbers
  • HMDB31598
Metabolite Identification
Common Name2,3-Pentanedione
Description2,3-Pentanedione, also known as acetyl propionyl or pentan-2,3-dione, belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms. 2,3-Pentanedione is a sweet, butter, and caramel tasting compound. 2,3-Pentanedione has been detected, but not quantified, in several different foods, such as coffee and coffee products, tamarinds, cauliflowers, green beans, and cereals and cereal products.
Structure
Data?1563862145
Synonyms
ValueSource
Acetyl propionylChEBI
AcetylpropionylChEBI
Ethyl methyl diketoneChEBI
2,3-PentadioneHMDB
2,3-PentandioneHMDB
2,3-Pentane-dioneHMDB
23-PENTANEDIONEHMDB
Benzil-related compound, 43HMDB
CH3C(O)C(O)C2H5HMDB
FEMA 2841HMDB
Pentan-2,3-dioneHMDB
Pentane-2,3-dioneHMDB
2,3-PentanedioneChEBI
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Namepentane-2,3-dione
Traditional Nameacetyl propionyl
CAS Registry Number600-14-6
SMILES
CCC(=O)C(C)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-5(7)4(2)6/h3H2,1-2H3
InChI KeyTZMFJUDUGYTVRY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-diketones. These are organic compounds containing two ketone groups on two adjacent carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-diketones
Alternative Parents
Substituents
  • Alpha-diketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-52 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility66.7 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility59 g/LALOGPS
logP0.33ALOGPS
logP1.1ChemAxon
logS-0.23ALOGPS
pKa (Strongest Acidic)16.16ChemAxon
pKa (Strongest Basic)-8.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.17 m³·mol⁻¹ChemAxon
Polarizability10.3 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
DarkChem[M+H]+121.65531661259
DarkChem[M-H]-115.23731661259
DeepCCS[M+H]+125.0730932474
DeepCCS[M-H]-123.17530932474
DeepCCS[M-2H]-159.00730932474
DeepCCS[M+Na]+133.43830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3-PentanedioneCCC(=O)C(C)=O1031.7Standard polar33892256
2,3-PentanedioneCCC(=O)C(C)=O600.0Standard non polar33892256
2,3-PentanedioneCCC(=O)C(C)=O699.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3-Pentanedione,1TMS,isomer #1CC=C(O[Si](C)(C)C)C(C)=O986.6Semi standard non polar33892256
2,3-Pentanedione,1TMS,isomer #1CC=C(O[Si](C)(C)C)C(C)=O961.6Standard non polar33892256
2,3-Pentanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CC1000.8Semi standard non polar33892256
2,3-Pentanedione,1TMS,isomer #2C=C(O[Si](C)(C)C)C(=O)CC982.3Standard non polar33892256
2,3-Pentanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CC)O[Si](C)(C)C1179.3Semi standard non polar33892256
2,3-Pentanedione,2TMS,isomer #1C=C(O[Si](C)(C)C)C(=CC)O[Si](C)(C)C1159.1Standard non polar33892256
2,3-Pentanedione,1TBDMS,isomer #1CC=C(O[Si](C)(C)C(C)(C)C)C(C)=O1231.5Semi standard non polar33892256
2,3-Pentanedione,1TBDMS,isomer #1CC=C(O[Si](C)(C)C(C)(C)C)C(C)=O1175.1Standard non polar33892256
2,3-Pentanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1223.8Semi standard non polar33892256
2,3-Pentanedione,1TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1167.1Standard non polar33892256
2,3-Pentanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CC)O[Si](C)(C)C(C)(C)C1617.7Semi standard non polar33892256
2,3-Pentanedione,2TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C(=CC)O[Si](C)(C)C(C)(C)C1570.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2,3-Pentanedione EI-B (Non-derivatized)splash10-002f-9000000000-0ce95c5163dd022c1c852017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2,3-Pentanedione EI-B (Non-derivatized)splash10-002f-9000000000-0ce95c5163dd022c1c852018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-Pentanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-6efb51c4de82549983462016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3-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 - 2,3-Pentanedione 10V, Positive-QTOFsplash10-0ue9-8900000000-9f2550c5ccdb885883f62016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 20V, Positive-QTOFsplash10-0f89-9400000000-aced3a08968c34c3c77d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 40V, Positive-QTOFsplash10-066r-9000000000-f2020a05efe30fe635a42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 10V, Negative-QTOFsplash10-0002-9000000000-937e1b88ba9d018bb1102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 20V, Negative-QTOFsplash10-0a4j-9000000000-d2f9ab3928212851b97c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 40V, Negative-QTOFsplash10-0a59-9000000000-f28c1dbd0dc8e76d03ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 10V, Negative-QTOFsplash10-052b-9000000000-7e24a3c06bbde998f5cc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 20V, Negative-QTOFsplash10-0a4i-9000000000-f7f96d401b9158db654b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 40V, Negative-QTOFsplash10-052f-9000000000-4c321f73c4f6865722d82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 10V, Positive-QTOFsplash10-0a4i-9000000000-494be75e817f2e253d612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 20V, Positive-QTOFsplash10-0a4l-9000000000-28924948f1a43030dfcd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3-Pentanedione 40V, Positive-QTOFsplash10-052f-9000000000-e151a32593049839df232021-09-24Wishart 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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008229
KNApSAcK IDNot Available
Chemspider ID11254
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylpropionyl
METLIN IDNot Available
PubChem Compound11747
PDB IDNot Available
ChEBI ID52774
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .