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Identification
YMDB IDYMDB01380
NameDiethyl butanedioate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionDiethyl succinate, also known as diethyl butanedioate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Diethyl succinate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • Butanedioic acid, diethyl ester
  • Clorius
  • Diethyl butanoate
  • Diethyl ester of butanedioic acid
  • Diethyl succinate
  • Diethylester kyseliny jantarove
  • Ethyl succinate
  • Succinic acid, diethyl ester
  • Diethyl succinic acid
  • Diethyl butanedioate
  • 1,4-Diethyl butanedioic acid
CAS number123-25-1
WeightAverage: 174.1944
Monoisotopic: 174.089208936
InChI KeyDKMROQRQHGEIOW-UHFFFAOYSA-N
InChIInChI=1S/C8H14O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-6H2,1-2H3
IUPAC Name1,4-diethyl butanedioate
Traditional IUPAC Namediethyl succinate
Chemical FormulaC8H14O4
SMILESCCOC(=O)CCC(=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
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • 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-21 °C
Experimental Properties
PropertyValueReference
Water Solubility19.1 mg/mL at 25 oC [EPA]PhysProp
LogP1.20 [CATZ,P & FRIEND,D (1989)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility16.7 g/LALOGPS
logP1.25ALOGPS
logP0.61ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity42.57 m³·mol⁻¹ChemAxon
Polarizability18.38 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
AppleFDB012012
ApricotFDB012012
ChocolateFDB012012
CookedFDB012012
CranberryFDB012012
FruitFDB012012
FruityFDB012012
GrapeFDB012012
MildFDB012012
MustyFDB012012
PeachFDB012012
PearFDB012012
WineFDB012012
YlangFDB012012
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)splash10-004i-6900000000-91b4bd8842569eab361fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-6900000000-7c630102d002ffd92fa9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-5900000000-447fd91aad895684276eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-6900000000-940ba7631d979c2aaa49JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-3900000000-7f6aa2df583c7cd0c94bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-004i-6900000000-91b4bd8842569eab361fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-6900000000-7c630102d002ffd92fa9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-5900000000-447fd91aad895684276eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fb9-6900000000-940ba7631d979c2aaa49JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-3900000000-7f6aa2df583c7cd0c94bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-9700000000-0513cf8f1fe77b0ed5afJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1900000000-7c0b11b197a1f93dfa39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004s-8900000000-83fc620612da3d1c067fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0571-9100000000-b25194b84647b74001b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-2900000000-30765b159461667846d4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0092-8900000000-cfb7037b49667188b454JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9200000000-44495c741511a36e6b58JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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 IDNot Available
HMDB IDHMDB0033838
Pubchem Compound ID31249
Kegg IDNot Available
ChemSpider ID13865630
FOODB IDFDB012012
Wikipedia IDDiethyl succinate
BioCyc IDNot Available