Record Information
Version1.0
Creation date2010-04-08 22:08:42 UTC
Update date2018-05-28 23:24:40 UTC
Primary IDFDB009603
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone
DescriptionWine lactone belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Wine lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Wine lactone is a sweet, coconut, and dill tasting compound. Wine lactone has been detected, but not quantified in, alcoholic beverages. This could make wine lactone a potential biomarker for the consumption of these foods.
CAS Number182699-77-0
Structure
Thumb
Synonyms
SynonymSource
3a,4,5,7a-tetrahydro-3,6-dimethyl- 2(3h)-benzofuranonebiospider
tetrahydro-3,6-dimethyl-2(3H)-benzofuranone, 3a,4,5,7abiospider
Predicted Properties
PropertyValueSource
Water Solubility4.12 g/LALOGPS
logP2.37ALOGPS
logP2.01ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.34 m³·mol⁻¹ChemAxon
Polarizability18.21 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H14O2
IUPAC name3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-one
InChI IdentifierInChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3
InChI KeyNQWBFQXRASPNLB-UHFFFAOYSA-N
Isomeric SMILESCC1C2CCC(C)=CC2OC1=O
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
Classification
Description belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9400000000-521a408a23ce51e6ed1dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-c114b3da9176078a9b5eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-6900000000-1ad72cd7b477799c9f91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9000000000-8c88f43e485a4ab8e752JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-b617020b1f5f2067d3ebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-3e51812fd3c6233c5fb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06dl-9700000000-fcbc57e848ff9d1efb62JSpectraViewer
ChemSpider ID4932494
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6427076
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29691
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS ID1757
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1582901
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
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  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