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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:32:43 UTC
NP-MRD IDNP0001316
Secondary Accession NumbersNone
Natural Product 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 a sweet and vanilla tasting compound. 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). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to plants 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. 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. Urinary VMA is elevated in patients with tumors that secrete catecholamines. Urinary VMA tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. VMA urinalysis tests can be used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. Vanillylmandelic acid (VMA) is produced in the liver and is a major product of norepinephrine and epinephrine metabolism excreted in the urine.
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
alpha,4-Dihydroxy-3-methoxybenzeneacetic acidHMDB
Α,4-dihydroxy-3-methoxybenzeneacetic acidHMDB
Vanillylmandelic acidHMDB
2-Hydroxy-2-phenylpropanoic acidMeSH
Hydroxyphenylpropionic acidMeSH
Chemical FormulaC9H10O5
Average Mass198.1727 Da
Monoisotopic Mass198.05282 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Pogostemon cablinLOTUS Database
Struthio camelus
Sus scrofa
Sus scrofa domestica
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point132 - 134 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000291
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021931
KNApSAcK IDC00052427
Chemspider ID643307
KEGG Compound IDC05584
BioCyc IDNot Available
BiGG ID46071
Wikipedia LinkVanillylmandelic acid
METLIN ID697
PubChem Compound736172
PDB IDNot Available
ChEBI ID1127735
Good Scents IDNot Available
References
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
  3. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
  4. Silbergeld EK, Chisolm JJ Jr: Lead poisoning: altered urinary catecholamine metabolites as indicators of intoxication in mice and children. Science. 1976 Apr 9;192(4235):153-5. [PubMed:1257763 ]
  5. Frank K, Raue F, Gottswinter J, Heinrich U, Meybier H, Ziegler R: Importance of early diagnosis and follow-up in multiple endocrine neoplasia (MEN II B). Eur J Pediatr. 1984 Dec;143(2):112-6. [PubMed:6394335 ]
  6. Takahashi S, Godse DD, Warsh JJ, Stancer HC: A gas chromatographic-mass spectrometric (GC-MS) assay for 3-methoxy-4-hydroxyphenethyleneglycol and vanilmandelic acid in human serum. Clin Chim Acta. 1977 Dec 1;81(2):182-92. [PubMed:589798 ]
  7. Suga K, Shimizu K, Nishigauchi K, Kume N, Kawamura T, Matsunaga N: [A case of bilateral adrenal neuroblastomas detected by bone scintigraphy]. Kaku Igaku. 1996 Dec;33(12):1337-42. [PubMed:9023440 ]
  8. Hartleb J, Eue S, Kemper A: Simultaneous analysis of homovanillic acid, 5-hydroxyindoleacetic acid, 3-methoxy-4-hydroxyphenylethylene glycol and vanilmandelic acid in plasma from alcoholics by high-performance liquid chromatography with electrochemical detection. Critical comparison of solid-phase and liquid-liquid extraction methods. J Chromatogr. 1993 Dec 22;622(2):161-71. [PubMed:7512090 ]
  9. Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7. [PubMed:687548 ]
  10. Saran RK, Sahuja RC, Gupta NN, Hasan M, Bhargava KP, Shanker K, Kishor K: 3-Methoxy-4-hydroxyphenylglycol in cerebrospinal fluid and vanillylmandelic acid in urine of humans with hypertension. Science. 1978 Apr 21;200(4339):317-8. [PubMed:635588 ]
  11. Strittmatter M, Grauer M, Isenberg E, Hamann G, Fischer C, Hoffmann KH, Blaes F, Schimrigk K: Cerebrospinal fluid neuropeptides and monoaminergic transmitters in patients with trigeminal neuralgia. Headache. 1997 Apr;37(4):211-6. [PubMed:9150615 ]
  12. Zambotti F, Blau K, King GS, Campbell S, Sandler M: Monoamine metabolites and related compounds in human amniotic fluid: assay by gas chromatography and gas chromatography-mass spectrometry. Clin Chim Acta. 1975 Jun 20;61(3):247-56. [PubMed:1149252 ]
  13. Drebing CJ, Freedman R, Waldo M, Gerhardt GA: Unconjugated methoxylated catecholamine metabolites in human saliva. Quantitation methodology and comparison with plasma levels. Biomed Chromatogr. 1989 Sep;3(5):217-20. [PubMed:2804429 ]
  14. Bostrom B, Mirkin BL: Elevation of cerebrospinal fluid catecholamine metabolites in patients with intracranial tumors of neuroectodermal origin. J Clin Oncol. 1987 Jul;5(7):1090-7. [PubMed:3598613 ]
  15. Afonso D, Castellanos MA, Rodriguez M: Determination of monoamines and indoles in amniotic fluid by high-performance liquid chromatography-electrochemical detection. J Chromatogr. 1990 Jun 8;528(1):101-9. [PubMed:1696583 ]