Record Information
Version1.0
Creation date2010-04-08 22:09:57 UTC
Update date2018-05-29 18:27:55 UTC
Primary IDFDB012018
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methyl-gamma-butyrolactone
Description4-Methyl-gamma-butyrolactone is a flavouring agent. It is found in peach, strawberry jam, tomato, wheat bread, Swiss cheese, Gruyere de Comte cheese, heated butter, cooked beef, white wine, red wine, coffee, black tea, roasted filbert, roasted peanut and Bourbon vanilla.
CAS Number57129-69-8
Structure
Thumb
Synonyms
SynonymSource
4-Hydroxypentanoic acid lactoneChEBI
4-Hydroxyvaleric acid lactoneChEBI
4-Methyl-4-hydroxybutanoic acid lactoneChEBI
4-Methyl-gamma-butyrolactoneChEBI
4-PentanolideChEBI
4-ValerolactoneChEBI
gamma-PentalactoneChEBI
gamma-PentanolactoneChEBI
4-Hydroxypentanoate lactoneGenerator
4-Hydroxyvalerate lactoneGenerator
4-Methyl-4-hydroxybutanoate lactoneGenerator
4-Methyl-g-butyrolactoneGenerator
4-Methyl-γ-butyrolactoneGenerator
g-PentalactoneGenerator
Γ-pentalactoneGenerator
g-PentanolactoneGenerator
Γ-pentanolactoneGenerator
Dihydro-5-methyl-2(3H)-furanoneChEBI
g-ValerolactoneGenerator
Γ-valerolactoneGenerator
4-Hydroxypentanoic acid g-lactonedb_source
4-Valerolacetonebiospider
5-Methyldihydro-2(3H)-furanonebiospider
5-Methyltetrahydrofuran-2-onebiospider
Dihydro-5-methyl-2-furanonebiospider
FEMA 3103db_source
g-Methylbutyrolactonedb_source
gamma-Valerolactonebiospider
Tetrahydro-5-methyl-2-furanonedb_source
Predicted Properties
PropertyValueSource
Water Solubility92.6 g/LALOGPS
logP0.36ALOGPS
logP0.57ChemAxon
logS-0.03ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.73 m³·mol⁻¹ChemAxon
Polarizability10.16 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H8O2
IUPAC name5-methyloxolan-2-one
InChI IdentifierInChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
InChI KeyGAEKPEKOJKCEMS-UHFFFAOYSA-N
Isomeric SMILESCC1CCC(=O)O1
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 59.98%; H 8.05%; O 31.96%DFC
Melting Point242.15 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056u-9000000000-7c79f68cacbc95c0ea48View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-056u-9000000000-7c79f68cacbc95c0ea48View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-9000000000-6c4e9500ba034d9524aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-3900000000-2daa06af8bff34a31a4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9500000000-f8a8c8887cd21f939e43View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-e9d8edd5c37160a8ed5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-6b4c492a247987f11177View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-9000000000-c3119840ef26293d0addView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-2fafb85814b3a8bd3267View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a6u-9000000000-9d68020f06bf659a559bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID7633
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID7921
Pubchem Substance IDNot Available
ChEBI ID48569
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33840
CRC / DFC (Dictionary of Food Compounds) IDHCP51-X:HCP51-X
EAFUS ID3823
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1024031
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cocoa
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference