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Identification
YMDB IDYMDB01385
NameEthyl butanoate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthyl butanoate (ethyl butyrate) 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 butanoate is responsible for apple-like aromas, pineapple aromas and blue cheese aromas. The concentrations of ethyl ester decrease over time as an alcoholic beverage ages due to spontaneous hydrolysis.
Structure
Thumb
Synonyms
  • Butanoic acid, ethyl ester
  • Butyric acid, ethyl ester
  • Butyric ester
  • Butyric ether
  • ethyl 1-butyrate
  • ethyl butanoate (ethyl butyrate)
  • Ethyl butyrate
  • Ethyl ester of butanoic acid
  • Ethyl n-butanoate
  • Ethyl n-butyrate
  • n-Butyric acid ethyl ester
  • Butanoic acid ethyl ester
  • Butyric acid ethyl ester
  • Ethyl butanoate
  • Butanoate ethyl ester
  • Butyrate ethyl ester
  • Ethyl 1-butyric acid
  • Ethyl butanoic acid
  • Ethyl ester OF butanoate
  • Ethyl N-butanoic acid
  • Ethyl N-butyric acid
  • N-Butyrate ethyl ester
  • Ethyl butyric acid
  • FEMA 2427
CAS number105-54-4
WeightAverage: 116.1583
Monoisotopic: 116.083729628
InChI KeyOBNCKNCVKJNDBV-UHFFFAOYSA-N
InChIInChI=1S/C6H12O2/c1-3-5-6(7)8-4-2/h3-5H2,1-2H3
IUPAC Nameethyl butanoate
Traditional IUPAC Nameethyl butyrate
Chemical FormulaC6H12O2
SMILESCCCC(=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 DescriptorsNot Available
Physical Properties
StateLiquid
Charge0
Melting point-98 °C
Experimental Properties
PropertyValueReference
Water Solubility4.9 mg/mL at 20 oC [RIDDICK,JA et al. (1986)]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.8 g/LALOGPS
logP1.8ALOGPS
logP1.42ChemAxon
logS-0.99ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability13.24 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
AppleFDB012082
BananaFDB012082
CognacFDB012082
FruitFDB012082
FruityFDB012082
JuicyFDB012082
PineappleFDB012082
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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
  • 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 ID17968
HMDB IDHMDB0033889
Pubchem Compound ID7762
Kegg IDNot Available
ChemSpider ID7475
FOODB IDFDB012082
WikipediaEthyl_butyrate
BioCyc IDBUTYRIC_ACID