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Identification
YMDB IDYMDB01691
NameEthylvanillate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionEthylvanillate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Ethylvanillate is an extremely weak basic (essentially neutral) compound (based on its pKa). Ethylvanillate may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • 3-Methoxy-4-hydroxybenzoic acid, ethyl ester
  • 4-Hydroxy-3-methoxybenzoic acid ethyl ester
  • Benzoic acid, 4-hydroxy-3-methoxy-, ethyl ester
  • Ethyl 4-hydroxy-3-methoxybenzoate
  • Ethyl vanillate
  • m-Anisic acid, 4-hydroxy-, ethyl ester
  • Vanillic acid, ethyl ester
  • Ethylvanillic acid
CAS number617-05-0
WeightAverage: 196.1999
Monoisotopic: 196.073558872
InChI KeyULKIVNGMBPJKRW-UHFFFAOYSA-N
InChIInChI=1S/C10H12O4/c1-3-6-7(10(12)13)4-5-8(11)9(6)14-2/h4-5,11H,3H2,1-2H3,(H,12,13)
IUPAC Name2-ethyl-4-hydroxy-3-methoxybenzoic acid
Traditional IUPAC Name2-ethyl-4-hydroxy-3-methoxybenzoic acid
Chemical FormulaC10H12O4
SMILESCCC1=C(OC)C(O)=CC=C1C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • M-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point44 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.93 g/LALOGPS
logP1.81ALOGPS
logP2.13ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.4 m³·mol⁻¹ChemAxon
Polarizability19.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0faj-0900000000-be607ed0c14e3460bb9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-e82b364fbf05ab7b3a5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-0900000000-4eff59dee25187ddd7f6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8900000000-43163366453f23b62aebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-5ad809a14c62e92bb336JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uds-0900000000-7eff16f7cb9c567fc6a9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-3900000000-c3fe20e6c222743ef523JSpectraViewer
References
References:
  • Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID18615902
Kegg IDNot Available
ChemSpider ID13923027
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available