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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:14 UTC
Update Date2021-09-14 15:20:35 UTC
HMDB IDHMDB0032333
Secondary Accession Numbers
  • HMDB32333
Metabolite Identification
Common Name4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone
Description4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone, also known as 4-methyl-4-vinyl-1,4-butanolide or 4-methyl-4-vinylbutyrolactone, 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. 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone has been detected, but not quantified in, several different foods, such as teas (Camellia sinensis), black tea, herbal tea, red tea, and grape wine. This could make 4-hydroxy-4-methyl-5-hexenoic acid gamma lactone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone.
Structure
Data?1563862250
Synonyms
ValueSource
4-Hydroxy-4-methyl-5-hexenoate g lactoneGenerator
4-Hydroxy-4-methyl-5-hexenoate gamma lactoneGenerator
4-Hydroxy-4-methyl-5-hexenoate γ lactoneGenerator
4-Hydroxy-4-methyl-5-hexenoic acid g lactoneGenerator
4-Hydroxy-4-methyl-5-hexenoic acid γ lactoneGenerator
4-Methyl-4-vinyl-1,4-butanolideHMDB
4-Methyl-4-vinylbutyrolactoneHMDB
4-Methyl-5-hexen-4-olideHMDB
5-Ethenyl-5-methyl-2(3H)-furanoneHMDB
5-Ethenyl-5-methyloxolan-2-oneHMDB
5-Ethenyldihydro-5-methyl-2(3H)-furanoneHMDB
5-Methyl-5-vinyldihydro-2(3H)-furanoneHMDB
Dihydro-5-methyl-5-vinyl-2(3H)-furanoneHMDB
Dihydro-5-methyl-5-vinylfuran-2(3H)-oneHMDB
Laquo gammaraquo -vinyl-laquo gammaraquo -valerolactoneHMDB
Lavander lactoneHMDB
Lavender lactoneHMDB
Chemical FormulaC7H10O2
Average Molecular Weight126.155
Monoisotopic Molecular Weight126.068079562
IUPAC Name5-ethenyl-5-methyloxolan-2-one
Traditional Name5-ethenyl-5-methyloxolan-2-one
CAS Registry Number1073-11-6
SMILES
CC1(CCC(=O)O1)C=C
InChI Identifier
InChI=1S/C7H10O2/c1-3-7(2)5-4-6(8)9-7/h3H,1,4-5H2,2H3
InChI KeyQESPSAHXYXIGBG-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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.66 g/LALOGPS
logP10(1.49) g/LALOGPS
logP10(1.22) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.78 m³·mol⁻¹ChemAxon
Polarizability13.15 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]+128.6631661259
DarkChem[M-H]-122.54831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-4-methyl-5-hexenoic acid gamma lactoneCC1(CCC(=O)O1)C=C1679.1Standard polar33892256
4-Hydroxy-4-methyl-5-hexenoic acid gamma lactoneCC1(CCC(=O)O1)C=C978.0Standard non polar33892256
4-Hydroxy-4-methyl-5-hexenoic acid gamma lactoneCC1(CCC(=O)O1)C=C1026.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone EI-B (Non-derivatized)splash10-0bvl-9200000000-288aefec213df99a77a22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone EI-B (Non-derivatized)splash10-0bvl-9200000000-288aefec213df99a77a22018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gdl-9000000000-55b8188b9d924876ed812016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 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 - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Positive-QTOFsplash10-004i-2900000000-fa61e83a2322102e7fa12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Positive-QTOFsplash10-0kdi-9400000000-9f4df5bc0701e56a44412016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Positive-QTOFsplash10-1000-9000000000-456d2a5525482b95dc802016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Negative-QTOFsplash10-004i-3900000000-173ee627c0b4ffa9718f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Negative-QTOFsplash10-0059-9600000000-1e06bc9a5ae34c41f0552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Negative-QTOFsplash10-002f-9000000000-92debe2684efa4ba31fe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Negative-QTOFsplash10-014i-9200000000-caa88bd7cedaf2124bc12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Negative-QTOFsplash10-0ugi-9000000000-6cb361c9af78395315722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Negative-QTOFsplash10-0gbc-9000000000-71460161a8d02092ce262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 10V, Positive-QTOFsplash10-0ar0-9300000000-f7141c758cf6863f1f632021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 20V, Positive-QTOFsplash10-0a4i-9000000000-a1fc0ad10dc676a370412021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-4-methyl-5-hexenoic acid gamma lactone 40V, Positive-QTOFsplash10-0uxu-9000000000-471a27dbfa771562fb4b2021-09-23Wishart 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
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 IDFDB004423
KNApSAcK IDNot Available
Chemspider ID92625
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102550
PDB IDNot Available
ChEBI ID52939
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. (). EAFUS: Everything Added to Food in the United States.. .