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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:56 UTC
HMDB IDHMDB0000549
Secondary Accession Numbers
  • HMDB00549
Metabolite Identification
Common Namegamma-Butyrolactone
DescriptionGamma-butyrolactone (GBL), also known as 1,4-butanolide or 1,4-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. GBL can also be classified as a tetrahydrofuran substituted by an oxo group at position 2. Gamma-butyrolactone is soluble in ethanol and moderately miscible in water. Gamma-butyrolactone is a sweet, caramel, and creamy tasting compound. Gamma-butyrolactone exists in all living species, ranging from bacteria to plants to humans. It can be endogenously produced from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. Outside of the human body, gamma-butyrolactone has been detected, but not quantified in, several different foods, such as pepper (c. annuum), yellow bell peppers, orange bell peppers, soy beans, evergreen blackberries and a variety of wines (at a concentration of 5 ug/mL) (PMID: 15939164 ). This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. Gamma-butyrolactone is rapidly converted into gamma-hydroxybutyrate by paraoxonase (lactonase) enzymes, found in the blood. Because it can serve as a prodrug for gamma-hydroxybutyrate (GHB), Gamma-butyrolactone is commonly used as a recreational CNS depressant with effects similar to those of barbiturates. Industrially gamma-butyrolactone is used as a common solvent for polymers and alcohols, a chemical intermediate, a raw material for pharmaceuticals, and as a paint stripper, superglue remover, and a stain remover.
Structure
Data?1676999696
Synonyms
ValueSource
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
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Nameoxolan-2-one
Traditional Namebutyrolactone
CAS Registry Number96-48-0
SMILES
O=C1CCCO1
InChI Identifier
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
InChI KeyYEJRWHAVMIAJKC-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
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-45 °CNot Available
Boiling Point204.00 to 205.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP-0.64HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+115.28231661259
DarkChem[M-H]-109.71131661259
AllCCS[M+H]+117.71832859911
AllCCS[M-H]-118.24632859911
DeepCCS[M+H]+124.59430932474
DeepCCS[M-H]-122.69830932474
DeepCCS[M-2H]-158.14430932474
DeepCCS[M+Na]+132.67930932474
AllCCS[M+H]+117.732859911
AllCCS[M+H-H2O]+112.532859911
AllCCS[M+NH4]+122.632859911
AllCCS[M+Na]+124.032859911
AllCCS[M-H]-118.232859911
AllCCS[M+Na-2H]-122.032859911
AllCCS[M+HCOO]-126.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
gamma-ButyrolactoneO=C1CCCO11629.3Standard polar33892256
gamma-ButyrolactoneO=C1CCCO1826.1Standard non polar33892256
gamma-ButyrolactoneO=C1CCCO1917.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - gamma-Butyrolactone EI-B (Non-derivatized)splash10-004l-9000000000-500445dc73cb69119e6b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Butyrolactone EI-B (Non-derivatized)splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Butyrolactone EI-B (Non-derivatized)splash10-002f-9000000000-d3df175d3315ed446e142017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Butyrolactone EI-B (Non-derivatized)splash10-004l-9000000000-500445dc73cb69119e6b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Butyrolactone EI-B (Non-derivatized)splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - gamma-Butyrolactone EI-B (Non-derivatized)splash10-002f-9000000000-d3df175d3315ed446e142018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Butyrolactone GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9000000000-bd4b413f20907d13a1072016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - gamma-Butyrolactone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004l-9000000000-2fc3f4165b5808b41e932014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Butyrolactone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-9000000000-4a6de93563809aa51a332012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Butyrolactone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-9000000000-4a6de93563809aa51a332012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Butyrolactone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000i-9000000000-b5163f6eb1e8004e61a92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Butyrolactone EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-004l-9000000000-1066d349a6023c66dd642012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Butyrolactone EI-B (JEOL JMS-D-3000) , Positive-QTOFsplash10-0006-9000000000-c2f6d51e7b2f9ce1e9f12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - gamma-Butyrolactone EI-B (HITACHI M-80B) , Positive-QTOFsplash10-002f-9000000000-d3df175d3315ed446e142012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 10V, Negative-QTOFsplash10-000i-9000000000-fb7c9ada825a0c62979f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 20V, Negative-QTOFsplash10-000l-9000000000-95fda8a898d02f7e71ff2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 40V, Negative-QTOFsplash10-000l-9000000000-c8282365f175b61ca8c02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 10V, Negative-QTOFsplash10-000i-9000000000-ec20127c74818b1f634d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 20V, Negative-QTOFsplash10-052r-9000000000-86d21b481322417edf812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 40V, Negative-QTOFsplash10-0006-9000000000-4f454124d6cece18a2122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 10V, Positive-QTOFsplash10-000i-9000000000-507998514018a44c4cf02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 20V, Positive-QTOFsplash10-000l-9000000000-d4ec4947321dfb11fab42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 40V, Positive-QTOFsplash10-0006-9000000000-b2a1436205f5365513b02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 10V, Positive-QTOFsplash10-000i-9000000000-709821dd006aa045c8b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 20V, Positive-QTOFsplash10-0006-9000000000-ffe2d9473d85a58305c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - gamma-Butyrolactone 40V, Positive-QTOFsplash10-0006-9000000000-a4219a074939d10a0f5f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adipose Tissue
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.28 +/- 0.16 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04699
Phenol Explorer Compound IDNot Available
FooDB IDFDB003392
KNApSAcK IDC00053167
Chemspider ID7029
KEGG Compound IDC01770
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Butyrolactone
METLIN ID5533
PubChem Compound7302
PDB IDNot Available
ChEBI ID42639
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1028441
References
Synthesis ReferenceZhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang. Process for preparation of g-butyrolactone with high yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 13 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Fukui Y, Matsusima E, Muramoto K, Nagai N, Ohama K, Yamashita K: Validation of a simple gas chromatographic-mass spectrometric method for the determination of gamma-butyrolactone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):73-80. [PubMed:12535840 ]
  2. Thupari JN, Landree LE, Ronnett GV, Kuhajda FP: C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9498-502. Epub 2002 Jun 11. [PubMed:12060712 ]
  3. Wood M, Laloup M, Samyn N, Morris MR, de Bruijn EA, Maes RA, Young MS, Maes V, De Boeck G: Simultaneous analysis of gamma-hydroxybutyric acid and its precursors in urine using liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2004 Nov 12;1056(1-2):83-90. [PubMed:15595536 ]
  4. Quintanilla RA, Orellana DI, Gonzalez-Billault C, Maccioni RB: Interleukin-6 induces Alzheimer-type phosphorylation of tau protein by deregulating the cdk5/p35 pathway. Exp Cell Res. 2004 Apr 15;295(1):245-57. [PubMed:15051507 ]
  5. Knust U, Hull WE, Spiegelhalder B, Bartsch H, Strowitzki T, Owen RW: Analysis of enterolignan glucuronides in serum and urine by HPLC-ESI-MS. Food Chem Toxicol. 2006 Jul;44(7):1038-49. Epub 2006 Feb 20. [PubMed:16488523 ]
  6. Selmaoui B, Aymard N, Lambrozo J, Touitou Y: Evaluation of the nocturnal levels of urinary biogenic amines in men exposed overnight to 50-Hz magnetic field. Life Sci. 2003 Oct 31;73(24):3073-82. [PubMed:14550848 ]
  7. Oshima I, Saito S, Shiota K, Miyake A, Oka Y, Nakayama R: Kinetic study on disappearance of gamma-butyrolactone-gamma-carbonyl-L-histidyl-L-prolinamide (DN-1417) from plasma using a radioimmunoassay for DN-1417 isobutylamide. J Pharmacobiodyn. 1983 Mar;6(3):202-8. [PubMed:6410041 ]
  8. Yeatman DT, Reid K: A study of urinary endogenous gamma-hydroxybutyrate (GHB) levels. J Anal Toxicol. 2003 Jan-Feb;27(1):40-2. [PubMed:12587682 ]
  9. Elliott S, Burgess V: The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages. Forensic Sci Int. 2005 Jul 16;151(2-3):289-92. doi: 10.1016/j.forsciint.2005.02.014. [PubMed:15939164 ]