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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-13 05:47:24 UTC
Update Date2017-10-23 19:04:09 UTC
HMDB IDHMDB0003843
Secondary Accession Numbers
  • HMDB03843
Metabolite Identification
Common NameGamma-Caprolactone
Description4-hydroxy-Hexanoic acid gamma-lactone is occasionally found as a volatile component of human urine. 4-hydroxy-Hexanoic acid gamma-lactone has been found in the polar fraction of human blood. Biological fluids such as blood and urine have been shown to contain a large number of components, some of them volatiles (low boiling point) apparently present in all individuals, while others such are much more variable. In some cases differences up to an order of magnitude are observed. Although some of these changes may have dietary origins, others seem to be characteristic of the individual. (PMID: 5556886 , 6480763 , 15835926 ).
Structure
Thumb
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
g-CaprolactoneGenerator
γ-caprolactoneGenerator
4-Hydroxyhexanoate lactoneGenerator
g-Ethyl-N-butyrolactoneGenerator
γ-ethyl-N-butyrolactoneGenerator
g-EthylbutyrolactoneGenerator
γ-ethylbutyrolactoneGenerator
g-HexanolactoneGenerator
γ-hexanolactoneGenerator
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
DescriptionThis compound belongs to the class of chemical entities known as gamma butyrolactones. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassLactones
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
Disposition

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-18 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-9000000000-33d7bffec7b90b244b58View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-9000000000-44158ddc3fb5887db72fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002r-9000000000-043fff98e80d69a0aef2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-cab1026e3eff252b355aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9400000000-8fc4e90e7c0513f35b2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052f-9000000000-264ec24375d9874e27c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-775242b739802c329ceeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0570-9000000000-33d7bffec7b90b244b58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0570-9000000000-106225f6b2045cabc0f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-002r-9000000000-c2681c456564a462e5bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-6a7b9f7c95a7bbd6d545View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9300000000-c2191b168940bbcbfcffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9000000000-2ca0f454e2ac7dd3126fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-493fdb9ba4ad5c9105fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-9600000000-6600fa8b57b7c1f87013View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-414e486262314b7d9f34View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008075
KNApSAcK IDNot Available
Chemspider ID12232
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12756
PDB IDNot Available
ChEBI ID422598
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 ]