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Identification
YMDB IDYMDB01357
NameEthyl 3-hexenoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthyl 3-hexenoate is a volatile ethyl ester found in wine and produced during fermentation by yeast. Ethyl esters are formed by the reaction of ethanol with a fatty acid. They typically have pleasant sweet aromas. The concentrations of ethyl ester decrease over time as a wine ages due to spontaneous hydrolysis.
Structure
Thumb
Synonyms
  • Ethyl (3E)-3-hexenoate
  • ethyl hex-3-enoate
  • Ethyl (e)-hex-3-enoate
CAS number2396-83-0
WeightAverage: 142.1956
Monoisotopic: 142.099379692
InChI KeyVTSFIPHRNAESED-AATRIKPKSA-N
InChIInChI=1S/C8H14O2/c1-3-5-6-7-8(9)10-4-2/h5-6H,3-4,7H2,1-2H3/b6-5+
IUPAC Nameethyl hex-3-enoate
Traditional IUPAC Name3-hexenoic acid, ethyl ester
Chemical FormulaC8H14O2
SMILES[H]C(=C([H])C([H])([H])C([H])([H])[H])C([H])([H])C(=O)OC([H])([H])C([H])([H])[H]
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.17 g/LALOGPS
logP2.49ALOGPS
logP1.95ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.71 m³·mol⁻¹ChemAxon
Polarizability16.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
FreshNot Available
FruityNot Available
GreenNot Available
MetallicNot Available
PineappleNot Available
SweetNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB59908
Pubchem Compound ID61312
Kegg IDNot Available
ChemSpider ID55250
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available