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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:24:04 UTC
Update Date2022-03-07 02:54:30 UTC
HMDB IDHMDB0035422
Secondary Accession Numbers
  • HMDB35422
Metabolite Identification
Common Name4-Butyl-gamma-butyrolactone
Description4-Butyl-gamma-butyrolactone, also known as 4-octanolide or 5-butyldihydro-2(3H)-furanone, 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, 4-butyl-gamma-butyrolactone is considered to be a fatty ester. 4-Butyl-gamma-butyrolactone is a sweet, coconut, and creamy tasting compound. 4-Butyl-gamma-butyrolactone is found, on average, in the highest concentration within pineapples (Ananas comosus) and bilberries (Vaccinium myrtillus). 4-Butyl-gamma-butyrolactone has also been detected, but not quantified in, several different foods, such as asparagus (Asparagus officinalis), tortilla chip, peaches (Prunus persica), blackberries (Rubus), and papayas (Carica papaya). This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods. 4-Butyl-gamma-butyrolactone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-Butyl-gamma-butyrolactone.
Structure
Data?1563862716
Synonyms
ValueSource
4-OctanolideChEBI
5-Butyldihydro-2(3H)-furanoneChEBI
5-Butyloxolan-2-oneChEBI
8-oxo-5-OctanolideChEBI
Dihydro-5-butyl-2(3H)-furanoneChEBI
gamma-Butyl-gamma-butyrolactoneChEBI
gamma-ButylbutyrolactoneChEBI
gamma-N-Butyl-gamma-butyrolactoneChEBI
gamma-Octanoic lactoneChEBI
Octan-4-olideChEBI
Octano-1,4-lactoneChEBI
g-Butyl-g-butyrolactoneGenerator
Γ-butyl-γ-butyrolactoneGenerator
g-ButylbutyrolactoneGenerator
Γ-butylbutyrolactoneGenerator
g-N-Butyl-g-butyrolactoneGenerator
Γ-N-butyl-γ-butyrolactoneGenerator
g-Octanoic lactoneGenerator
Γ-octanoic lactoneGenerator
4-Butyl-g-butyrolactoneGenerator
4-Butyl-γ-butyrolactoneGenerator
4-Butyl-4-hydroxybutyric acid lactoneHMDB
4-Hydroxyoctanoic acid lactoneHMDB
5-Butyl-tetrahydro-furan-2-oneHMDB
5-Butyldihydrofuran-2(3H)-oneHMDB
5-butylhydro-2(3H)-FuranoneHMDB
5-butyltetrahydro-2-FuranoneHMDB
FEMA 2796HMDB
gamma-OctalactoneHMDB
gamma-OctanolactoneHMDB
Octanoic acid, gamma lactoneHMDB
Octanolide-1,4HMDB
g-OctanolideGenerator
Γ-octanolideGenerator
(R)-4-OctanolideMeSH
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Name5-butyloxolan-2-one
Traditional Name5-butyloxolan-2-one
CAS Registry Number104-50-7
SMILES
CCCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
InChI KeyIPBFYZQJXZJBFQ-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
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point234.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP1.432 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.96 g/LALOGPS
logP1.94ALOGPS
logP1.98ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.45 m³·mol⁻¹ChemAxon
Polarizability16.25 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]+131.55231661259
DarkChem[M-H]-128.28631661259
DeepCCS[M+H]+137.31630932474
DeepCCS[M-H]-134.55330932474
DeepCCS[M-2H]-171.49530932474
DeepCCS[M+Na]+146.28730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Butyl-gamma-butyrolactoneCCCCC1CCC(=O)O11926.3Standard polar33892256
4-Butyl-gamma-butyrolactoneCCCCC1CCC(=O)O11191.6Standard non polar33892256
4-Butyl-gamma-butyrolactoneCCCCC1CCC(=O)O11274.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Butyl-gamma-butyrolactone EI-B (Non-derivatized)splash10-000i-9000000000-b38e079f829f45a525dd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Butyl-gamma-butyrolactone EI-B (Non-derivatized)splash10-000i-9000000000-b38e079f829f45a525dd2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Butyl-gamma-butyrolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-1ba786a1eb6b754fd6002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Butyl-gamma-butyrolactone 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-Butyl-gamma-butyrolactone 10V, Positive-QTOFsplash10-0006-4900000000-8714044bd4ab585a2f692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Positive-QTOFsplash10-000x-9200000000-1001b4cf846542fcb2e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Positive-QTOFsplash10-0006-9000000000-a476386c50ad13ec24a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 10V, Negative-QTOFsplash10-0006-3900000000-d0af9ad440391bb2c0582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Negative-QTOFsplash10-0007-9700000000-5dbe2305cdbd99c63dbf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Negative-QTOFsplash10-0007-9000000000-247831545f03580fc9cc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 10V, Negative-QTOFsplash10-0006-0900000000-5720fb1a64f78a2627942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Negative-QTOFsplash10-0006-2900000000-65c7450bb61b4b3696f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Negative-QTOFsplash10-0006-9100000000-24ceeecd97274ff6ec492021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 10V, Positive-QTOFsplash10-0a4l-9300000000-6bd6c22f833b03943fd02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Positive-QTOFsplash10-05po-9000000000-d22b0d5f17d4f20fe77b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Positive-QTOFsplash10-052f-9000000000-ee08758371db084712ce2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H 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 IDFDB014100
KNApSAcK IDNot Available
Chemspider ID7418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7704
PDB IDNot Available
ChEBI ID145738
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1006542
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.. .