Ethyl octanoate (YMDB01389)

Identification
YMDB IDYMDB01389
NameEthyl octanoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthyl octanoate, also known as ethyl caprylate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a significant number of articles have been published on Ethyl octanoate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-heptanecarboxylate
  • caprylate
  • Caprylic acid ethyl ester
  • Ethyl caprylate
  • Ethyl ester octanoic acid
  • Ethyl n-octanoate
  • Ethyl octoate
  • Ethyl octylate
  • n-caprylate
  • n-Caprylic acid ethyl ester
  • n-octanoate
  • n-octoate
  • n-octylate
  • octanoic acid ethyl ester (ethyl octanoate)
  • Octanoic acid, ethyl ester
  • octanoic acid, ion(1-)
  • octylate
  • Caprylate ethyl ester
  • Ethyl caprylic acid
  • Ethyl N-octanoic acid
  • Ethyl octanoic acid
  • Caprylic acid ethylester
  • FEMA 2449
CAS number106-32-1
WeightAverage: 172.2646
Monoisotopic: 172.146329884
InChI KeyYYZUSRORWSJGET-UHFFFAOYSA-N
InChIInChI=1S/C10H20O2/c1-3-5-6-7-8-9-10(11)12-4-2/h3-9H2,1-2H3
IUPAC Nameethyl octanoate
Traditional IUPAC Nameethyl octanoate
Chemical FormulaC10H20O2
SMILESCCCCCCCC(=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-43.1 °C
Experimental Properties
PropertyValueReference
Water Solubility0.0701 mg/mL at 25 oC [SUZUKI,T (1991)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP3.94ALOGPS
logP3.2ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity49.79 m³·mol⁻¹ChemAxon
Polarizability21.5 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
ApricotFDB019907
BananaFDB019907
BrandyFDB019907
FatFDB019907
FruitFDB019907
FruityFDB019907
PearFDB019907
SweetFDB019907
WaxyFDB019907
WineFDB019907
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.0232 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 1Brewer's yeastPMID: 10357281
0.145 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 2Brewer's yeastPMID: 10357281
0.337 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 3Brewer's yeastPMID: 10357281
0.261 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 4Brewer's yeastPMID: 10357281
2 ± 0 uM Wickerman synthetiv mediumAnaerobic at day 6Brewer's yeastPMID: 10357281
0.342 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 7Brewer's yeastPMID: 10357281
1 ± 0 uM Wickerman synthetiv mediumAnaerobic at day 8Brewer's yeastPMID: 10357281
3 ± 0 uM Wickerman synthetiv mediumAnaerobic at day 9Brewer's yeastPMID: 10357281
1 ± 0 uM Wickerman synthetiv mediumAnaerobic at day 10Brewer's yeastPMID: 10357281
0.389 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 13Brewer's yeastPMID: 10357281
0.517 ± 0.0 uM Wickerman synthetiv mediumAnaerobic at day 14Brewer's yeastPMID: 10357281
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-1900000000-95c74d7036b5a8476b30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-9200000000-8db5abfa0094ff1f7642JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0553-9100000000-317ca99bd3ea06f6d867JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-1900000000-95c74d7036b5a8476b30JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-9200000000-8db5abfa0094ff1f7642JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0553-9100000000-317ca99bd3ea06f6d867JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002e-9100000000-0866832e236b5ee594d5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1900000000-1d78b8efbbd825f2dbbdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bk-9700000000-1b878ca6d2e6d08b3845JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-f64d719de500bd734389JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-1900000000-102b60231f0fecc5f403JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ba-5900000000-7b5bd9742762eb90554aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-9200000000-7ea4aa19396bbe2c11afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0900000000-56155225d7006537002aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-2900000000-1f14c81f2c18588237c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9100000000-e3e04e195042aedb57e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-9200000000-bd7b666d93358310c5ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-b5ddca15b4a092c55bf0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-7dfa33f7aa41c15b8501JSpectraViewer
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
  • 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 ID27594
HMDB IDHMDB0040195
Pubchem Compound ID7799
Kegg IDC12292
ChemSpider ID7511
FOODB IDFDB019907
Wikipedia IDEthyl octanoate
BioCyc IDNot Available