Record Information
Version1.0
Creation date2010-04-08 22:11:26 UTC
Update date2019-11-26 03:10:41 UTC
Primary IDFDB014730
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methyl-4-butyl-gamma-butyrolactone
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). Quercuslactone a is a burnt, celery, and coconut tasting compound. Quercuslactone a has been detected, but not quantified in, alcoholic beverages. This could make quercuslactone a a potential biomarker for the consumption of these foods.
CAS Number39212-23-2
Structure
Thumb
Synonyms
SynonymSource
(e)-WhiskylactoneHMDB
T-WhiskylactoneHMDB
trans-WhiskeylactoneHMDB
beta-Methyl-gamma-octalactoneHMDB
3-Methyl-4-butyl-g-butyrolactoneGenerator
3-Methyl-4-butyl-γ-butyrolactoneGenerator
2(3H)-Furanone, 5-butyldihydro-4-methyl-biospider
2(3H)-Furanone, dihydro, 5-butyl-4-methylbiospider
3-Methyl-4-butyl-gamma-butyrolactonemanual
3-Methyl-4-octanolidedb_source
4-Hydroxy-3-methyloctanoic acid lactonebiospider
5-Butyl-4-methyl-dihydro-2(3H)-furanonebiospider
5-Butyl-4-methyldihydro-2(3H)-furanonebiospider
5-Butyldihydro-4-methylfuran-2(3H)-onebiospider
cis-3-Methyl-4-octanolidebiospider
FEMA 3803db_source
Oaklactonedb_source
Quercuslactonedb_source
Whiskey lactonebiospider
Whisky lactonedb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H16O2
IUPAC name5-butyl-4-methyloxolan-2-one
InChI IdentifierInChI=1S/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3
InChI KeyWNVCMFHPRIBNCW-UHFFFAOYSA-N
Isomeric SMILESCCCCC1OC(=O)CC1C
Average Molecular Weight156.2221
Monoisotopic Molecular Weight156.115029756
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.19%; H 10.32%; O 20.48%DFC
Melting PointNot Available
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 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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID62900
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJVG77-P:JVG77-P
EAFUS ID1768
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1029501
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
tonka
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coumarin
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
toasted
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
celery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
burnt
  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