Ethyl hexanoate (YMDB01381)

Identification
YMDB IDYMDB01381
NameEthyl hexanoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthyl hexanoate 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 hexanoate is responsible for flowery/fruity aromas, e.g. pineapple, blackberry, apple-peel and strawberry aromas. The concentrations of ethyl ester decrease over time as an alcoholic beverage ages due to spontaneous hydrolysis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-hexanoate
  • 1-pentacarboxylate
  • 1-pentanecarboxylate
  • Acetic acid, butyl-, ethyl ester
  • butylacetate
  • caproate
  • Caproic acid ethyl ester
  • capronate
  • Ethyl butyl acetate
  • Ethyl caproate
  • Ethyl ester of hexanoic acid
  • Ethyl hexanoate
  • Ethyl hexoate
  • Ethyl n-hexanoate
  • Hexanoic acid, ethyl ester
  • hexoate
  • hexylate
  • n-caproate
  • n-Caproic acid ethyl ester
  • n-hexanoate
  • n-hexoate
  • n-hexylate
  • pentanecarboxylate
  • pentylformate
  • Ethyl N-hexanoat
  • Hexanoic acid ethyl ester
  • Caproate ethyl ester
  • Ethyl caproic acid
  • Ethyl ester OF hexanoate
  • Ethyl hexoic acid
  • Hexanoate ethyl ester
  • N-Caproate ethyl ester
  • Ethyl hexanoic acid
  • Caproic acid ethylester
  • Capronic ether absolute
  • Ethyl butyl acetate (dot)
  • Ethyl hexanoate (caproate)
  • FEMA 2439
  • Hexanoic acid, ethyl ester, mixt. with soybean oil epoxide
CAS number123-66-0
WeightAverage: 144.2114
Monoisotopic: 144.115029756
InChI KeySHZIWNPUGXLXDT-UHFFFAOYSA-N
InChIInChI=1S/C8H16O2/c1-3-5-6-7-8(9)10-4-2/h3-7H2,1-2H3
IUPAC Nameethyl hexanoate
Traditional IUPAC Nameethyl hexanoate
Chemical FormulaC8H16O2
SMILESCCCCCC(=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-67 °C
Experimental Properties
PropertyValueReference
Water Solubility0.629 mg/mL at 25 oC [SUZUKI,T (1991)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP2.92ALOGPS
logP2.31ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.59 m³·mol⁻¹ChemAxon
Polarizability17.32 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
Apple peelFDB019921
BananaFDB019921
FruitFDB019921
FruityFDB019921
GreenFDB019921
PineappleFDB019921
SweetFDB019921
WaxyFDB019921
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.0901 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 1Brewer's yeastPMID: 10357281
0.0624 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 2Brewer's yeastPMID: 10357281
0.943 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 3Brewer's yeastPMID: 10357281
0.978 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 4Brewer's yeastPMID: 10357281
2 ± 0 uM Wickerman synthetiv mediumAnaerobic at day 6Brewer's yeastPMID: 10357281
0.638 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 7Brewer's yeastPMID: 10357281
0.86 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 8Brewer's yeastPMID: 10357281
2 ± 0 uM Wickerman synthetiv mediumAnaerobic at day 9Brewer's yeastPMID: 10357281
0.749 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 10Brewer's yeastPMID: 10357281
0.18 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 13Brewer's yeastPMID: 10357281
0.458 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 14Brewer's yeastPMID: 10357281
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01rl-9000000000-c4a428f4af3678af55b5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01tl-9000000000-b511103509087502c6dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01rl-9000000000-c4a428f4af3678af55b5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01tl-9000000000-b511103509087502c6dfJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-3f4b554f930a16c91f85JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-5900000000-1d6e0542ed766431edd9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9200000000-ea176c85160cde938be4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-f08ba8bdf4f45654e5e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-7900000000-58755a27868e3915af73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-c8e3af4a4f844e662a58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9000000000-a50363e5c24481fa9a2dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-f273dbe7b19bad8e9910JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-c688f81973ea98568c64JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-9000000000-7e778dcba6da2ac098b2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r7-9100000000-4e527c99ae1b67a09e91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fu-9000000000-26df2f6eb35fbbfa03c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-b6c469234b2e28e58a21JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Vianna, E., Ebeler, S. E. (2001). "Monitoring ester formation in grape juice fermentations using solid phase microextraction coupled with gas chromatography-mass spectrometry." J Agric Food Chem 49:589-595.11261997
  • Gallardo-Chacon, J. J., Vichi, S., Lopez-Tamames, E., Buxaderas, S. (2010). "Changes in the Sorption of Diverse Volatiles by Saccharomyces cerevisiae Lees during Sparkling Wine Aging." J Agric Food Chem :.21073195
  • 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
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • 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
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID86055
HMDB IDHMDB0040209
Pubchem Compound ID31265
Kegg IDNot Available
ChemSpider ID29005
FOODB IDFDB019921
Wikipedia IDEthyl hexanoate
BioCyc IDNot Available