Ethyl heptanoate (YMDB01474)

Identification
YMDB IDYMDB01474
NameEthyl heptanoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthyl heptanoate is a volatile aroma ester extracted from yeast and produced during fermentation of alcoholic beverages. Its odor is similar to grape. Ethyl heptanoate is a volatile ethyl ester found in alcoholic beverages and produced during fermentation by yeast. Ethyl esters are formed by the reaction of ethanol with a fatty acid. Ethyl heptanoate has an aroma associated with grape. The concentrations of ethyl ester decrease over time as an alcoholic beverage ages due to spontaneous hydrolysis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-hexanecarboxylate
  • Aether oenanthicus
  • Cognac oil
  • enanthate
  • Enanthic acid ethyl ester
  • enanthylate
  • Enanthylic ether
  • ethyl enantate
  • Ethyl enanthate
  • Ethyl ester of heptanoic acid
  • Ethyl heptanoic acid
  • Ethyl heptoate
  • Ethyl heptoic acid
  • Ethyl heptylate
  • Ethyl n-heptanoate
  • Ethyl n-heptanoic acid
  • Ethyl oenanthate
  • Ethyl oenanthylate
  • Grape oil
  • Heptanoic acid, ethyl ester
  • heptanoic acid, ion(1-)
  • heptoate
  • heptylate
  • n-heptanoate
  • n-heptoate
  • n-heptylate
  • oenanthate
  • Oenanthic ether
  • oenanthylate
  • Oleum vitis viniferae
  • Wine oil
  • Heptanoic acid ethyl ester
  • Enanthate ethyl ester
  • Ethyl enanthic acid
  • Heptanoate ethyl ester
  • Ethyl heptanoate
CAS number106-30-9
WeightAverage: 158.238
Monoisotopic: 158.13067982
InChI KeyTVQGDYNRXLTQAP-UHFFFAOYSA-N
InChIInChI=1S/C9H18O2/c1-3-5-6-7-8-9(10)11-4-2/h3-8H2,1-2H3
IUPAC Nameethyl heptanoate
Traditional IUPAC Namewine oil
Chemical FormulaC9H18O2
SMILESCCCCCCC(=O)OCC
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-66.1 °C
Experimental Properties
PropertyValueReference
Water Solubility0.29 mg/mL at 25 oC [SUZUKI,T (1991)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP3.39ALOGPS
logP2.76ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity45.19 m³·mol⁻¹ChemAxon
Polarizability19.56 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
CognacFDB008200
FruitFDB008200
FruityFDB008200
MelonFDB008200
PineappleFDB008200
PlumFDB008200
RumFDB008200
WineFDB008200
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)splash10-01rf-9100000000-a353a37f3708e92c2326JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01rf-9100000000-a353a37f3708e92c2326JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-9100000000-c72923dafa1d44429851JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-9000000000-9edaac31bd434dc702a7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0059-9000000000-36de8965c80f28b4afafJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-040r-9000000000-c237534a2830dcfb14d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-01rf-9100000000-26f45931ddf7c8d9be90JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-8f4bb59da32813b7c338JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08mj-9500000000-70417efdee62172288edJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-14c4bdffefb7863d3375JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1900000000-80d3ab1a9e4d27b04976JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-5900000000-99f864a6cd5be1c2bb2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-9200000000-0cc7b2dca091fc5d8b6dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu9-9300000000-c393817198ce2e94c629JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0596-9000000000-9144c2f812b39480c03fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ff3765e20f589914f031JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0900000000-21c18f41de3d04acc532JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-9600000000-96a4f6f14aec365c5229JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-bcea0bb57c9b884b7e98JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Verstrepen, K. J., Van Laere, S. D., Vanderhaegen, B. M., Derdelinckx, G., Dufour, J. P., Pretorius, I. S., Winderickx, J., Thevelein, J. M., Delvaux, F. R. (2003). "Expression levels of the yeast alcohol acetyltransferase genes ATF1, Lg-ATF1, and ATF2 control the formation of a broad range of volatile esters." Appl Environ Microbiol 69:5228-5237.12957907
  • 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:Gogichaishvili, E. A. Conditions of formation and accumulation of ethyl enanthate. Tr. Inst. Sadovodstva, Vinogradarstva i Vinodeliya, Akad. Sel'skokhoz. Nauk Gruz. SSR (1961), 13 413-18.
External Links:
ResourceLink
CHEBI ID32362
HMDB IDHMDB00798
Pubchem Compound ID7797
Kegg IDNot Available
ChemSpider ID7509
FOODB IDFDB008200
WikipediaEthyl_heptanoate
BioCyc IDNot Available