Record Information
Version1.0
Creation date2010-04-08 22:05:47 UTC
Update date2019-11-26 02:59:09 UTC
Primary IDFDB003392
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namegamma-Butyrolactone
Descriptiongamma-Butyrolactone, also known as 1,4-butanolide or 4-hydroxy-butanoate, 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-butyrolactone is considered to be a fatty ester lipid molecule. gamma-Butyrolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Butyrolactone exists in all living species, ranging from bacteria to humans. gamma-Butyrolactone is a sweet, caramel, and creamy tasting compound. gamma-Butyrolactone has been detected, but not quantified in, several different foods, such as tortilla chips, red bell peppers, tea, green bell peppers, and evergreen blackberries. This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. gamma-Butyrolactone is a potentially toxic compound.
CAS Number96-48-0
Structure
Thumb
Synonyms
SynonymSource
1,2-ButanolideChEBI
1,4-ButanolideChEBI
1,4-LactoneChEBI
4-ButyrolactoneChEBI
4-Deoxytetronic acidChEBI
4-Hydroxybutyric acid lactoneChEBI
ButyrolactoneChEBI
Dihydro-2(3H)-furanoneChEBI
gamma-ButanolactoneChEBI
gamma-Hydroxybutyric acid lactoneChEBI
gamma-HydroxybutyrolactoneChEBI
Tetrahydrofuran-2-oneChEBI
4-DeoxytetronateGenerator
4-Hydroxybutyrate lactoneGenerator
g-ButanolactoneGenerator
Γ-butanolactoneGenerator
g-Hydroxybutyrate lactoneGenerator
g-Hydroxybutyric acid lactoneGenerator
gamma-Hydroxybutyrate lactoneGenerator
Γ-hydroxybutyrate lactoneGenerator
Γ-hydroxybutyric acid lactoneGenerator
g-HydroxybutyrolactoneGenerator
Γ-hydroxybutyrolactoneGenerator
g-ButyrolactoneGenerator
Γ-butyrolactoneGenerator
1-Oxacyclopentan-2-oneHMDB
2,3,4,5-Tetrahydro-2-furanoneHMDB
2-OxolanoneHMDB
2-OxotetrahydrofuranHMDB
4,5-Dihydro-2(3H)-furanoneHMDB
4-ButanolideHMDB
4-Hydroxy-butanoateHMDB
4-Hydroxy-butanoic acidHMDB
4-Hydroxy-butanoic acid g-lactoneHMDB
4-HydroxybutanoateHMDB
4-Hydroxybutanoic acidHMDB
4-Hydroxybutanoic acid lactoneHMDB
Butyric acid lactoneHMDB
g-ButalactoneHMDB
g-ButyryllactoneHMDB
gamma-ButalactoneHMDB
gamma-ButyryllactoneHMDB
GBLHMDB
Paint clean gHMDB
Tetrahydro-2-furanoneHMDB
4 ButyrolactoneHMDB
gamma ButyrolactoneHMDB
Furanone, tetrahydro 2HMDB
1,4 ButanolideHMDB
4 Hydroxybutyric acid lactoneHMDB
Lactone, 4-hydroxybutyric acidHMDB
gamma-ButyrolactoneMeSH
1-Oxacyclopentane-2-onebiospider
1,4-Butyrolactonebiospider
2-Dihydrofuranonebiospider
2(3H)-dihydrofuranonebiospider
3-Hydroxybutyric acid lactonebiospider
4-Hydroxy-Butanoic acid g-lactonebiospider
4-Hydroxybutanoic acid, «gamma»-lactonebiospider
4-Hydroxybutyric acid, «gamma»-lactonebiospider
Butyryl lactonebiospider
Butyrylactonebiospider
Dihydro-2-furanonebiospider
Dihydrofuran-2(3H)-onebiospider
Dihyro-2-furanonebiospider
FEMA 3291db_source
gamma-Hydroxybutyric acid cyclic esterbiospider
gamma-Lactone 4-hydroxy-butanoic acidbiospider
gamma-Lactone 4-hydroxy-butyric acidbiospider
gamma-Lactone 4-hydroxybutanoic acidbiospider
gamma-Lactone 4-hydroxybutyric acidbiospider
Hydroxybutanoic acid lactonebiospider
γ-butanolactoneGenerator
γ-butyrolactoneGenerator
γ-hydroxybutyrate lactoneGenerator
γ-hydroxybutyric acid lactoneGenerator
γ-hydroxybutyrolactoneGenerator
Predicted Properties
PropertyValueSource
Water Solubility238 g/LALOGPS
logP-0.11ALOGPS
logP0.15ChemAxon
logS0.44ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.31 m³·mol⁻¹ChemAxon
Polarizability8.23 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6O2
IUPAC nameoxolan-2-one
InChI IdentifierInChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
InChI KeyYEJRWHAVMIAJKC-UHFFFAOYSA-N
Isomeric SMILESO=C1CCCO1
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.81%; H 7.02%; O 37.17%DFC
Melting Point-45
Boiling PointBp12 89°DFC
Experimental Water Solubility1000 mg/mLWEAST,RC (1972)
Experimental logP-0.64HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd0 1.44DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004l-9000000000-500445dc73cb69119e6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-d3df175d3315ed446e14JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004l-9000000000-500445dc73cb69119e6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9000000000-d3df175d3315ed446e14JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-bd4b413f20907d13a107JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-4a6de93563809aa51a33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-4a6de93563809aa51a33JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-b5163f6eb1e8004e61a9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-004l-9000000000-1066d349a6023c66dd64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-002f-9000000000-d3df175d3315ed446e14JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-507998514018a44c4cf0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-d4ec4947321dfb11fab4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b2a1436205f5365513b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-fb7c9ada825a0c62979fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9000000000-95fda8a898d02f7e71ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9000000000-c8282365f175b61ca8c0JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-2fc3f4165b5808b41e93JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID7029
ChEMBL IDCHEMBL95681
KEGG Compound IDC01770
Pubchem Compound ID7302
Pubchem Substance IDNot Available
ChEBI ID42639
Phenol-Explorer IDNot Available
DrugBank IDDB04699
HMDB IDHMDB00549
CRC / DFC (Dictionary of Food Compounds) IDCXH55-B:CXH55-B
EAFUS ID1728
Dr. Duke IDGAMMA-BUTYROLACTONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDGBL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID96-48-0
GoodScent IDrw1028441
SuperScent IDNot Available
Wikipedia ID4-Hydroxybutyric acid lactone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
neurotoxic50910 A poison that interferes with the functions of the nervous system.CHEBI
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
caramel
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
creamy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).