Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:16:07 UTC
Update Date2022-03-07 02:55:09 UTC
HMDB IDHMDB0037026
Secondary Accession Numbers
  • HMDB37026
Metabolite Identification
Common Name3,4-Dimethyl-1,2-cyclopentanedione
Description3,4-Dimethyl-1,2-cyclopentanedione belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. 3,4-Dimethyl-1,2-cyclopentanedione is a sweet, anise, and balsam tasting compound. 3,4-Dimethyl-1,2-cyclopentanedione has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 3,4-dimethyl-1,2-cyclopentanedione a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,4-Dimethyl-1,2-cyclopentanedione.
Structure
Data?1563862966
Synonyms
ValueSource
2-Hydroxy-3,4-dimethyl-2-cyclopenten-1-oneHMDB
3,4-Dimethyl-1,2-cyclopentadioneHMDB
FEMA 3268HMDB
Chemical FormulaC7H10O2
Average Molecular Weight126.1531
Monoisotopic Molecular Weight126.068079564
IUPAC Name3,4-dimethylcyclopentane-1,2-dione
Traditional Name3,4-dimethylcyclopentane-1,2-dione
CAS Registry Number13494-06-9
SMILES
CC1CC(=O)C(=O)C1C
InChI Identifier
InChI=1S/C7H10O2/c1-4-3-6(8)7(9)5(4)2/h4-5H,3H2,1-2H3
InChI KeyWGAVDEVFJDQIMZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point71 - 72 °CNot Available
Boiling Point187.37 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility121100 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.796 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility22.7 g/LALOGPS
logP1.03ALOGPS
logP1.72ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)16.71ChemAxon
pKa (Strongest Basic)-8.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.51 m³·mol⁻¹ChemAxon
Polarizability13.2 ųChemAxon
Number of Rings1ChemAxon
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]+128.78431661259
DarkChem[M-H]-123.6731661259
DeepCCS[M+H]+131.39430932474
DeepCCS[M-H]-128.6330932474
DeepCCS[M-2H]-165.48730932474
DeepCCS[M+Na]+140.4130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-1,2-cyclopentanedioneCC1CC(=O)C(=O)C1C1732.4Standard polar33892256
3,4-Dimethyl-1,2-cyclopentanedioneCC1CC(=O)C(=O)C1C1020.1Standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedioneCC1CC(=O)C(=O)C1C1079.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4-Dimethyl-1,2-cyclopentanedione,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)CC1C1228.9Semi standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)CC1C1189.7Standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TMS,isomer #2CC1C=C(O[Si](C)(C)C)C(=O)C1C1249.7Semi standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TMS,isomer #2CC1C=C(O[Si](C)(C)C)C(=O)C1C1205.2Standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1C1374.6Semi standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,2TMS,isomer #1CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=CC1C1393.8Standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1C1478.9Semi standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)CC1C1416.7Standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TBDMS,isomer #2CC1C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1C1483.1Semi standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,1TBDMS,isomer #2CC1C=C(O[Si](C)(C)C(C)(C)C)C(=O)C1C1435.3Standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1C1853.7Semi standard non polar33892256
3,4-Dimethyl-1,2-cyclopentanedione,2TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC1C1762.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9100000000-1497b7ff09debc96483e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 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 - 3,4-Dimethyl-1,2-cyclopentanedione 10V, Positive-QTOFsplash10-004i-2900000000-5c24366c60b870acaba32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 20V, Positive-QTOFsplash10-056r-9500000000-3aca1df1ff900bf41aea2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 40V, Positive-QTOFsplash10-0zfr-9000000000-108636ad5f3a92d28bbf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 10V, Negative-QTOFsplash10-004i-0900000000-d406083cb1baecbcdb022015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 20V, Negative-QTOFsplash10-004i-1900000000-9814cce09bcc5c236f102015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 40V, Negative-QTOFsplash10-0pvl-9100000000-726367b03709009b462d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 10V, Negative-QTOFsplash10-004i-0900000000-e8a652cde2a23224db302021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 20V, Negative-QTOFsplash10-004i-9600000000-5bf72d607e8eac0619f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 40V, Negative-QTOFsplash10-01bc-9200000000-969a706cf6604e54ee812021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 10V, Positive-QTOFsplash10-004i-6900000000-1fba1a01be746a6302f82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 20V, Positive-QTOFsplash10-066u-9000000000-9ae7707cdd35387b89f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Dimethyl-1,2-cyclopentanedione 40V, Positive-QTOFsplash10-00kf-9000000000-11c26c9e2bd8380923652021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016006
KNApSAcK IDNot Available
Chemspider ID55541
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61633
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012731
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.. .