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Identification
YMDB IDYMDB01605
Name3-Methyl-4-octanolide
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionQuercuslactone a, also known as (e)-whiskylactone, 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. Quercuslactone a is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 2(3H)-Furanone, dihydro, 5-butyl-4-methyl
  • 5-Butyl-4-methyldihydro-2(3H)-furanone
  • 5-Butyldihydro-4-methyl-2(3H)-furanone
  • 5-butyldihydro-4-methylfuran-2(3H)-one
  • (e)-Whiskylactone
  • T-Whiskylactone
  • trans-Whiskeylactone
  • beta-Methyl-gamma-octalactone
  • 3-Methyl-4-butyl-g-butyrolactone
  • 3-Methyl-4-butyl-γ-butyrolactone
CAS number39212-23-2
WeightAverage: 156.2221
Monoisotopic: 156.115029756
InChI KeyWNVCMFHPRIBNCW-UHFFFAOYSA-N
InChIInChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3
IUPAC Name5-butyl-4-methyloxolan-2-one
Traditional IUPAC Namecis-3-methyl-4-octanolide
Chemical FormulaC9H16O2
SMILESCCCCC1OC(=O)CC1C
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 DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP2.69ALOGPS
logP2.34ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity42.92 m³·mol⁻¹ChemAxon
Polarizability18.11 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BurntFDB014730
CeleryFDB014730
CoconutFDB014730
CoumarinFDB014730
NuttyFDB014730
ToastedFDB014730
TonkaFDB014730
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-52b91f8a190dc4d70837JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-52b91f8a190dc4d70837JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-7bc62b21db7f07d62ea5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-eb60924d7db73dd90686JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066s-9400000000-a3cfdd4ac40cb7f70218JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-bf75c35ed005be1d8a74JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-764fd7c479fc1a34fab7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-2900000000-0d927d1c064257fc8d86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200000000-42902cc652512e92509cJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0035307
Pubchem Compound ID41285
Kegg IDNot Available
ChemSpider ID56625
FOODB IDFDB014730
Wikipedia IDNot Available
BioCyc IDNot Available