Record Information
Version1.0
Creation date2011-09-21 00:05:25 UTC
Update date2015-10-09 22:29:32 UTC
Primary IDFDB021931
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVanillylmandelic acid
DescriptionVanillylmandelic acid, also known as vanillylmandelate or VMA, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Vanillylmandelic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to humans. Vanillylmandelic acid is a sweet and vanilla tasting compound. Vanillylmandelic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, colorectal cancer, and brunner syndrome; vanillylmandelic acid has also been linked to several inborn metabolic disorders including phenylketonuria and aromatic l-amino acid decarboxylase deficiency.
CAS Number55-10-7
Structure
Thumb
Synonyms
SynonymSource
VanillylmandelateGenerator
(4-Hydroxy-3-methoxyphenyl)glycolateHMDB
(4-Hydroxy-3-methoxyphenyl)glycolic acidHMDB
3-Methoxy-4-hydroxy-mandelic acidHMDB
3-Methoxy-4-hydroxymandelateHMDB
3-Methoxy-4-hydroxymandelic acidHMDB
3-Methoxy-4-hydroxyphenylhydroxyacetateHMDB
3-Methoxy-4-hydroxyphenylhydroxyacetic acidHMDB
4'-Hydroxy-3'-methoxymandelateHMDB
4'-Hydroxy-3'-methoxymandelic acidHMDB
4-Hydroxy 3-methoxymandelic acidHMDB
4-Hydroxy-3-methoxy-DL-mandelateHMDB
4-Hydroxy-3-methoxy-DL-mandelic acidHMDB
4-Hydroxy-3-methoxy-mandelateHMDB
4-Hydroxy-3-methoxy-mandelic acidHMDB
4-Hydroxy-3-methoxymandelateHMDB
4-Hydroxy-3-methoxymandelic acidHMDB
DL-3-Methoxy-4-hydroxymandelateHMDB
DL-3-Methoxy-4-hydroxymandelic acidHMDB
DL-4-Hydroxy-3-methoxymandelateHMDB
DL-4-Hydroxy-3-methoxymandelic acidHMDB
DL-VanillomandelateHMDB
DL-Vanillomandelic acidHMDB
DL-VanillylmandelateHMDB
DL-Vanillylmandelic acidHMDB
HMMAHMDB
Hydroxymethoxymandelic acidHMDB
Lopac-H-0131HMDB
Vainillylmandelic acidHMDB
VanillinmandelateHMDB
Vanillinmandelic acidHMDB
VanillomandelateHMDB
Vanillomandelic acidHMDB
Vanillyl-mandelic acidHMDB
Vanillylmandellic acidHMDB
Vanillymandelic acidHMDB
VanilmandelateHMDB
Vanilmandelic acidHMDB
Vanilylmandelic acidHMDB
Vanyl-mandelic acidHMDB
Vanylmandelic acidHMDB
VMAHMDB
2-Phenyllactic acidHMDB
VMA CPDHMDB
Atrolactic acidHMDB
Atrolactic acid monosodium salt, (S)-isomerHMDB
Atrolactic acid, (+-)-isomerHMDB
Hydroxymethylmandelic acidHMDB
3-methoxy-4-hydroxy-mandelic acidhmdb
3-methoxy-4-hydroxymandelic acidhmdb
4-hydroxy 3-methoxymandelic acidhmdb
4-hydroxy-3-methoxy-Mandelatehmdb
4-hydroxy-3-methoxy-Mandelic acidhmdb
DL-vanillomandelatehmdb
DL-vanillomandelic acidhmdb
DL-vanillylmandelatehmdb
DL-vanillylmandelic acidhmdb
vainillylmandelic acidhmdb
vanillyl-mandelic acidhmdb
vanillylmandellic acidhmdb
vanillymandelic acidhmdb
vanilylmandelic acidhmdb
vanyl-mandelic acidhmdb
vanylmandelic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility5.16 g/LALOGPS
logP0.94ALOGPS
logP0.43ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.15 m³·mol⁻¹ChemAxon
Polarizability18.45 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H10O5
IUPAC name(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
InChI IdentifierInChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1
InChI KeyCGQCWMIAEPEHNQ-QMMMGPOBSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)[C@H](O)C(O)=O
Average Molecular Weight198.1727
Monoisotopic Molecular Weight198.05282343
Classification
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-97b85fd5a9736a5d5eb0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009t-7396100000-b5450c24921a68f5f6b3JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000b-0900000000-1e2dedd8e81249787b29JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000i-0900000000-3d2cd918dc6b76dfba3fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-2900000000-b543807e43e5091abb53JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-0900000000-04d80bfab4984d07e479JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-23d4830296b7ea07f0d5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fki-5900000000-9b9364530caece4b6c12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-1308d37a2313f5479365JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmj-0900000000-bcdff30bcec2389ffef6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-3900000000-cd2db271b5a0926adfebJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID643307
ChEMBL IDCHEMBL1603851
KEGG Compound IDC05584
Pubchem Compound ID736172
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00291
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID46071
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1486281
SuperScent IDNot Available
Wikipedia IDVanillylmandelic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference