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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 05:47:24 UTC
Update Date2021-10-13 04:42:27 UTC
HMDB IDHMDB0003843
Secondary Accession Numbers
  • HMDB03843
Metabolite Identification
Common NameGamma-Caprolactone
DescriptionGamma-Caprolactone, also known as 4-ethyl-4-butanolide or 4-hexanolide, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, Gamma-caprolactone is considered to be a fatty ester lipid molecule. Gamma-Caprolactone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Gamma-Caprolactone exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, Gamma-caprolactone has been detected, but not quantified in several different foods, such as potato, cereals and cereal products, pomes, alcoholic beverages, and fruits. It is occasionally found as a volatile component of human urine. In some cases differences up to an order of magnitude are observed. It has been also found in the polar fraction of human blood.
Structure
Data?1582752288
Synonyms
ValueSource
4-Ethyl-4-butanolideChEBI
4-HexanolideChEBI
4-Hydroxyhexanoic acid lactoneChEBI
5-Ethyltetrahydro-2-furanoneChEBI
6-CaprolactoneChEBI
Dihydro-5-ethyl-2(3H)-furanoneChEBI
gamma-Ethyl-N-butyrolactoneChEBI
gamma-EthylbutyrolactoneChEBI
gamma-HexanolactoneChEBI
4-Hydroxyhexanoate lactoneGenerator
g-Ethyl-N-butyrolactoneGenerator
Γ-ethyl-N-butyrolactoneGenerator
g-EthylbutyrolactoneGenerator
Γ-ethylbutyrolactoneGenerator
g-HexanolactoneGenerator
Γ-hexanolactoneGenerator
g-CaprolactoneGenerator
Γ-caprolactoneGenerator
4-Ethylbutanolide (gamma-hexalactone)HMDB
4-Hydroxy-hexanoateHMDB
4-Hydroxy-hexanoic acidHMDB
4-Hydroxy-hexanoic acid gamma-lactoneHMDB
4-Hydroxy-hexanoic acid lactoneHMDB
4-HydroxyhexanoateHMDB
4-Hydroxyhexanoic acidHMDB
5-Ethyldihydro-2(3H)-furanoneHMDB
5-Ethyldihydrofuran-2(3H)-oneHMDB
gamma-Ethyl-gamma-butyrolactoneHMDB
gamma-HexalactoneHMDB
Hexa-4-olideHMDB
Hexanolide-1,4HMDB
TonkalideHMDB
ToukalideHMDB
Chemical FormulaC6H10O2
Average Molecular Weight114.1424
Monoisotopic Molecular Weight114.068079564
IUPAC Name5-ethyloxolan-2-one
Traditional Namegamma-hexalactone
CAS Registry Number695-06-7
SMILES
CCC1CCC(=O)O1
InChI Identifier
InChI=1S/C6H10O2/c1-2-5-3-4-6(7)8-5/h5H,2-4H2,1H3
InChI KeyJBFHTYHTHYHCDJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-18 °CNot Available
Boiling Point100.00 to 102.00 °C. @ 18.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP0.413 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility22.4 g/LALOGPS
logP0.77ALOGPS
logP1.09ChemAxon
logS-0.71ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.25 m³·mol⁻¹ChemAxon
Polarizability12.16 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]+123.6731661259
DarkChem[M-H]-119.02331661259
DeepCCS[M+H]+130.99330932474
DeepCCS[M-H]-128.82430932474
DeepCCS[M-2H]-164.9630932474
DeepCCS[M+Na]+139.36730932474
AllCCS[M+H]+124.632859911
AllCCS[M+H-H2O]+119.832859911
AllCCS[M+NH4]+129.232859911
AllCCS[M+Na]+130.532859911
AllCCS[M-H]-125.332859911
AllCCS[M+Na-2H]-127.832859911
AllCCS[M+HCOO]-130.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Gamma-CaprolactoneCCC1CCC(=O)O11672.9Standard polar33892256
Gamma-CaprolactoneCCC1CCC(=O)O1979.3Standard non polar33892256
Gamma-CaprolactoneCCC1CCC(=O)O11068.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Gamma-Caprolactone EI-B (Non-derivatized)splash10-0570-9000000000-33d7bffec7b90b244b582017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gamma-Caprolactone EI-B (Non-derivatized)splash10-0570-9000000000-44158ddc3fb5887db72f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gamma-Caprolactone EI-B (Non-derivatized)splash10-002r-9000000000-043fff98e80d69a0aef22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gamma-Caprolactone EI-B (Non-derivatized)splash10-0570-9000000000-33d7bffec7b90b244b582018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gamma-Caprolactone EI-B (Non-derivatized)splash10-0570-9000000000-44158ddc3fb5887db72f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Gamma-Caprolactone EI-B (Non-derivatized)splash10-002r-9000000000-043fff98e80d69a0aef22018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gamma-Caprolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-cab1026e3eff252b355a2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Gamma-Caprolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-9400000000-8fc4e90e7c0513f35b2b2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-052f-9000000000-264ec24375d9874e27c62012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-775242b739802c329cee2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone EI-B (Unknown) , Positive-QTOFsplash10-0570-9000000000-33d7bffec7b90b244b582012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone EI-B (HITACHI M-60) , Positive-QTOFsplash10-0570-9000000000-106225f6b2045cabc0f22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone EI-B (HITACHI M-80B) , Positive-QTOFsplash10-002r-9000000000-c2681c456564a462e5bc2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone 10V, Positive-QTOFsplash10-014i-9000000000-262d2422966b80201c0d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone 40V, Positive-QTOFsplash10-0006-9000000000-23a8252127edf957f9372021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Gamma-Caprolactone 20V, Positive-QTOFsplash10-00kf-9000000000-f6b5e0030b789716f7782021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 10V, Positive-QTOFsplash10-014i-5900000000-6a7b9f7c95a7bbd6d5452016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 20V, Positive-QTOFsplash10-014i-9300000000-c2191b168940bbcbfcff2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 40V, Positive-QTOFsplash10-0pbc-9000000000-2ca0f454e2ac7dd3126f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 10V, Negative-QTOFsplash10-03di-3900000000-493fdb9ba4ad5c9105fc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 20V, Negative-QTOFsplash10-03xr-9600000000-6600fa8b57b7c1f870132016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 40V, Negative-QTOFsplash10-0006-9000000000-414e486262314b7d9f342016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 10V, Negative-QTOFsplash10-03k9-9500000000-d90d57e21b78e509a53d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 20V, Negative-QTOFsplash10-08fr-9400000000-d4634fc480832e319c942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 40V, Negative-QTOFsplash10-052f-9000000000-ef10ab91c5fd551591e22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 10V, Positive-QTOFsplash10-014i-9200000000-ed4da47d3cda0847caf62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 20V, Positive-QTOFsplash10-00kf-9000000000-f3b9cd693e882a0887702021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Gamma-Caprolactone 40V, Positive-QTOFsplash10-052f-9000000000-fb0fd013f40b603156172021-09-23Wishart 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
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017640
KNApSAcK IDC00053196
Chemspider ID12232
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12756
PDB IDNot Available
ChEBI ID85235
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006382
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Khersonsky O, Tawfik DS: Structure-reactivity studies of serum paraoxonase PON1 suggest that its native activity is lactonase. Biochemistry. 2005 Apr 26;44(16):6371-82. [PubMed:15835926 ]
  3. Thoma H, Reiner J, Spiteller G: Profiles of strongly polar and less polar acids obtained from human blood, plasma and serum by two-step ultrafiltration. J Chromatogr. 1984 Jul 13;309(1):17-32. [PubMed:6480763 ]