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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:24:04 UTC
Update Date2019-07-23 06:18:36 UTC
HMDB IDHMDB0035422
Secondary Accession Numbers
  • HMDB35422
Metabolite Identification
Common Name4-Butyl-gamma-butyrolactone
Description4-Butyl-gamma-butyrolactone, also known as 5-butyldihydro-2(3H)-furanone or 4-hydroxyoctanoic acid lactone, 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 lipid molecule. 4-Butyl-gamma-butyrolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Butyl-gamma-butyrolactone is a sweet, coconut, and creamy tasting compound. Outside of the human body, 4-Butyl-gamma-butyrolactone is found, on average, in the highest concentration within pineapples and bilberries. 4-Butyl-gamma-butyrolactone has also been detected, but not quantified in, several different foods, such as fruits, asparagus, papaya, peachs, and evergreen blackberries. This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods.
Structure
Data?1563862716
Synonyms
ValueSource
4-Butyl-g-butyrolactoneGenerator
4-Butyl-γ-butyrolactoneGenerator
4-Butyl-4-hydroxybutyric acid lactoneHMDB
4-Hydroxyoctanoic acid lactoneHMDB
4-OctanolideHMDB
5-Butyl-tetrahydro-furan-2-oneHMDB
5-Butyldihydro-2(3H)-furanoneHMDB
5-Butyldihydrofuran-2(3H)-oneHMDB
5-Butylhydro-2(3H)-furanoneHMDB
5-Butyltetrahydro-2-furanoneHMDB
8-oxo-5-OctanolideHMDB
FEMA 2796HMDB
gamma-Butyl-gamma-butyrolactoneHMDB
gamma-N-Butyl-gamma-butyrolactoneHMDB
gamma-OctalactoneHMDB
gamma-Octanoic lactoneHMDB
gamma-OctanolactoneHMDB
Octan-4-olideHMDB
Octano-1,4-lactoneHMDB
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-b38e079f829f45a525ddSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9000000000-b38e079f829f45a525ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9100000000-1ba786a1eb6b754fd600Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-4900000000-8714044bd4ab585a2f69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9200000000-1001b4cf846542fcb2e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a476386c50ad13ec24a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-3900000000-d0af9ad440391bb2c058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-9700000000-5dbe2305cdbd99c63dbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9000000000-247831545f03580fc9ccSpectrum
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 IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .