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Record Information
Version1.0
Creation Date2016-07-13 19:43:00 UTC
Update Date2016-07-20 21:03:27 UTC
LmdbLMDB00129
Secondary Accession NumbersNone
Metabolite Identification
Common 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. Within humans, vanillylmandelic acid participates in a number of enzymatic reactions. In particular, vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol through the action of the enzyme catechol O-methyltransferase. Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide. In humans, vanillylmandelic acid is involved in the metabolic disorder called tyrosinemia type I. Vanillylmandelic acid is a sweet and vanilla tasting compound. Outside of the human body,. Vanillylmandelic acid, with regard to humans, has been found to be associated with several diseases such as brunner syndrome, colorectal cancer, and eosinophilic esophagitis; vanillylmandelic acid has also been linked to several inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency and phenylketonuria. In timed urine tests the quantity excreted (usually per 24 hours) is assessed along with creatinine clearance, and the quantity of cortisols, catecholamines, and metanephrines excreted is also measured. Urinary VMA is elevated in patients with tumors that secrete catecholamines. These tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. These hormones are released into the blood during times of physical or emotional stress, which are factors that may skew the results of the test. Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). Norepinephrine is one of the hormones produced by the adrenal glands, which are found on top of the kidneys. These urinalysis tests are used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla. Norepinephrine is metabolised into normetanephrine and VMA. It is produced via intermediary metabolites.
Structure
Thumb
Synonyms
ValueSource
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
(+)-4-Hydroxy-3-methoxymandelic acidHMDB
(+)-Vanilmandelic acidHMDB
(2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acidHMDB
(S)-4-Hydroxy-3-methoxymandelic acidHMDB
(alphaS)-alpha,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
(αS)-α,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
2-(4'-Hydroxy-3'-methoxyphenyl)-2-hydroxyethanoic acidHMDB
2-(4’-Hydroxy-3’-methoxyphenyl)-2-hydroxyethanoic acidHMDB
2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acidHMDB
4’-Hydroxy-3’-methoxymandelic acidHMDB
L-(+)-3-Methoxy-4-hydroxymandelic acidHMDB
Vanillylmandelic acidHMDB
alpha,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
α,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
Chemical FormulaC9H10O5
Average Molecular Weight198.1727
Monoisotopic Molecular Weight198.05282343
IUPAC Name(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional Name(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
CAS Registry Number55-10-7
SMILES
COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-97b85fd5a9736a5d5eb0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-009t-7396100000-b5450c24921a68f5f6b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000b-0900000000-1e2dedd8e81249787b29Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000i-0900000000-3d2cd918dc6b76dfba3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-2900000000-b543807e43e5091abb53Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-1c88ce4d32680e3379deSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-30e1c8cb4fa5443c687eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-c4c762f850d22fee6281Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-1308d37a2313f5479365Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmj-0900000000-bcdff30bcec2389ffef6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-3900000000-cd2db271b5a0926adfebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dj-9700000000-2c212037a037fcd229d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kg9-1900000000-81b2ab77bf3382c9f5deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4900000000-e3b77a4d29235649ecceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-0900000000-04d80bfab4984d07e479Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-23d4830296b7ea07f0d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fki-5900000000-9b9364530caece4b6c12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7t-0900000000-ac32d971a0581e8b6cb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-bce2f2854f319781df10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9700000000-311af8dc825e2dd02614Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
UrineDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
DrugBank IDNot Available
HMDB IDHMDB0000291
FooDB IDFDB021931
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46071
BioCyc IDNot Available
METLIN ID697
PDB IDNot Available
Wikipedia LinkVanillylmandelic acid
Chemspider ID643307
ChEBI ID1127735
PubChem Compound ID736172
Kegg Compound IDC05584
YMDB IDNot Available
ECMDB IDECMDB24029
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available