Identification
YMDB IDYMDB01802
NameVanillic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionVanillic acid, also known as vanillate or acid, vanillic, 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. Vanillic acid exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Vanillic acid.
Structure
Thumb
Synonyms
  • 4 Hydroxy 3 methoxybenzoic acid
  • 4-Hydroxy-3-methoxybenzoate
  • 4-Hydroxy-3-methoxybenzoic acid
  • Acid, 4-hydroxy-3-methoxybenzoic
  • Acid, P-hydroxy-m-methoxy-benzoic
  • Acid, vanillic
  • P Hydroxy m methoxy benzoic acid
  • P-Hydroxy-m-methoxy-benzoic acid
  • Vanillate
  • 3-Methoxy-4-hydroxybenzoate
  • 3-Methoxy-4-hydroxybenzoic acid
  • 4-Hydroxy-3-methoxy-benzoate
  • 4-Hydroxy-3-methoxy-benzoic acid
  • 4-Hydroxy-m-anisate
  • 4-Hydroxy-m-anisic acid
  • Acide vanillique
  • p-Vanillate
  • p-Vanillic acid
  • Protocatechuic acid 3-methyl ester
  • 2-Methoxy-4-carboxyphenol
  • Methylprotocatechuic acid
  • VA
  • m-Methoxy-p-hydroxy-benzoic acid
  • Vanillic acid
CAS number121-34-6
WeightAverage: 168.1467
Monoisotopic: 168.042258744
InChI KeyWKOLLVMJNQIZCI-UHFFFAOYSA-N
InChIInChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
IUPAC Name4-hydroxy-3-methoxybenzoic acid
Traditional IUPAC Namevanillic acid
Chemical FormulaC8H8O4
SMILESCOC1=CC(=CC=C1O)C(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 Descriptors
Physical Properties
StateSolid
Charge0
Melting point211.5 °C
Experimental Properties
PropertyValueReference
Water Solubility1.5 mg/mL at 14 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.43 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.7 g/LALOGPS
logP1.7ALOGPS
logP1.17ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.76 m³·mol⁻¹ChemAxon
Polarizability15.86 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BeanFDB000846
CreamyFDB000846
DairyFDB000846
MilkyFDB000846
PowderyFDB000846
SweetFDB000846
VanillaFDB000846
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 - GC-MS (2 TMS)splash10-0hp2-2691000000-8409d9c758b023c6576bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gb9-2900000000-ccd8d4a214bc1a7f08c5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0hp2-2691000000-8409d9c758b023c6576bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0g0b-2981000000-a58243e35d1e3a64d2aaJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4i-1900000000-851f4a1738be8dd91d47JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dj-7390000000-18c5f822b380ea00aa26JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0gb9-0900000000-0aa6709c16899e222086JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0gb9-2900000000-babed327a6e49c6f7d51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-105f33777cee542cf6dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-05fr-1900000000-a502792703fa2f211035JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-5900000000-037ef32f4c68a5252b92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9800000000-ecd60ac022f5fee1d5efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-066u-9300000000-c63f7f792794f3c748a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0923211100-7e9f357f7429cff05524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-014i-0923211100-7e9f357f7429cff05524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0923211100-7e9f357f7429cff05524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0900000000-8e112ffa4dcc7c08b0fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0429110000-57f8760ce65d48cdc01fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0uxr-0900000000-29a2674dccd1fa478bd5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-105f33777cee542cf6dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fr-1900000000-c4ce596998934098267bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-342964fa3647815dd1d2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0900000000-f16c365899f9d95733d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-5900000000-e5593db0a935e1534bc6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-6a1a2db582acd95348eaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0600-0900000000-eda6cfe601d63ed00f8dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-b2c1e3f6b255e94a10afJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0gb9-6900000000-c13506201c3612fc7ca5JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16632
HMDB IDHMDB00484
Pubchem Compound ID8468
Kegg IDC06672
ChemSpider ID8155
FOODB IDFDB000846
Wikipedia IDVanillic acid
BioCyc IDNot Available