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gamma-Butyrolactone (FDB003392)

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. gamma-Butyrolactone exists in all living species, ranging from bacteria to plants to humans. gamma-Butyrolactone is a sweet, caramel, and creamy tasting compound. gamma-Butyrolactone is found, on average, in the highest concentration within red wine. gamma-Butyrolactone has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), blackberries (Rubus), peppers (Capsicum annuum), pineapples (Ananas comosus), and yellow bell peppers (Capsicum annuum). This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on gamma-Butyrolactone.
CAS Number96-48-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-2fc3f4165b5808b41e932014-09-20View Spectrum
GC-MSgamma-Butyrolactone, non-derivatized, GC-MS Spectrumsplash10-004l-9000000000-500445dc73cb69119e6bSpectrum
GC-MSgamma-Butyrolactone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1Spectrum
GC-MSgamma-Butyrolactone, non-derivatized, GC-MS Spectrumsplash10-002f-9000000000-d3df175d3315ed446e14Spectrum
GC-MSgamma-Butyrolactone, non-derivatized, GC-MS Spectrumsplash10-004l-9000000000-500445dc73cb69119e6bSpectrum
GC-MSgamma-Butyrolactone, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1Spectrum
GC-MSgamma-Butyrolactone, non-derivatized, GC-MS Spectrumsplash10-002f-9000000000-d3df175d3315ed446e14Spectrum
Predicted GC-MSgamma-Butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9000000000-bd4b413f20907d13a107Spectrum
Predicted GC-MSgamma-Butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-4a6de93563809aa51a332012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-4a6de93563809aa51a332012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-b5163f6eb1e8004e61a92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-004l-9000000000-1066d349a6023c66dd642012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-002f-9000000000-d3df175d3315ed446e142012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-fb7c9ada825a0c62979f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9000000000-95fda8a898d02f7e71ff2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9000000000-c8282365f175b61ca8c02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-ec20127c74818b1f634d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9000000000-86d21b481322417edf812021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4f454124d6cece18a2122021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-507998514018a44c4cf02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-d4ec4947321dfb11fab42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b2a1436205f5365513b02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-709821dd006aa045c8b02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-ffe2d9473d85a58305c12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a4219a074939d10a0f5f2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).