You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB01747
NameMethyl vanillate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionMethyl vanillate, also known as vanillATE or vanillic acid, 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. Methyl vanillate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • 4-HYDROXY-3-METHOXYBENZOATE
  • 4-Hydroxy-3-methoxybenzoic acid methyl ester
  • Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester
  • Methyl 3-methoxy-4-hydroxybenzoate
  • Methyl 4-hydroxy-3-methoxybenzoate
  • Methyl ester of 4-hydroxy-3-methoxybenzoic acid
  • Methyl vanillate
  • VANILLATE
  • Vanillic acid methyl
  • Vanillic acid methyl ester
  • Vanillic acid, methyl ester
  • Methyl vanillic acid
  • 4-Hydroxy-3-methoxybenzoate methyl ester
  • Methyl 3-methoxy-4-hydroxybenzoic acid
  • VANILLic acid
  • Vanillate, methyl ester
  • Methylvanillate
  • Methylvanillic acid
  • Methyl 4-hydroxy-3-methoxybenzoic acid
  • 4-Hydroxy-3-methoxy methyl benzoate
  • 4-Hydroxy-3-methoxy methyl benzoic acid
CAS number3943-74-6
WeightAverage: 182.1733
Monoisotopic: 182.057908808
InChI KeyBVWTXUYLKBHMOX-UHFFFAOYSA-N
InChIInChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
IUPAC Namemethyl 4-hydroxy-3-methoxybenzoate
Traditional IUPAC Namevanillate
Chemical FormulaC9H10O4
SMILESCOC(=O)C1=CC(OC)=C(O)C=C1
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
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • M-methoxybenzoic acid or derivatives
  • Methoxyphenol
  • Benzoate ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point64 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.57 g/LALOGPS
logP2.12ALOGPS
logP1.52ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.53 m³·mol⁻¹ChemAxon
Polarizability18.09 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
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 ID46477
HMDB IDHMDB0240266
Pubchem Compound ID19844
Kegg IDNot Available
ChemSpider ID18693
FOODB IDFDB029771
Wikipedia IDMethyl group
BioCyc IDNot Available