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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:44 UTC
Secondary Accession Numbers
  • HMDB00913
Metabolite Identification
Common NameVanillactic acid
DescriptionVanillactic acid, also known as vanillactate or VLA, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Vanillactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillactic acid is a potentially toxic compound. Vanillactic acid has been linked to the inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency. Vanillactic acid is an acidic catecholamine metabolite present in normal human urine (PMID 7524950 ), in normal human CSF (PMID 7914240 ), and increased in the CSF of newborns with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency (PMID 12200739 ).
3-(3-Methoxy-4-hydroxyphenyl)lactic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)-lactic acidHMDB
3-(4-Hydroxy-3-methoxyphenyl)lactic acidHMDB
3-Methoxy-4-hydroxyphenyllactic acidHMDB
4-Hydroxy-3-methoxyphenyllactic acidHMDB
b-(4-Hydroxy-3-methoxyphenyl)lactic acidHMDB
beta-(4-Hydroxy-3-methoxyphenyl)lactic acidHMDB
Vanillyllactic acidHMDB
Vanillylactic acidHMDB
Vanillactic acidMeSH
Chemical FormulaC10H12O5
Average Molecular Weight212.1993
Monoisotopic Molecular Weight212.068473494
IUPAC Name2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoic acid
Traditional Namevanillactic acid
CAS Registry Number2475-56-1
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
  • 3-phenylpropanoic-acid
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Alpha-hydroxy acid
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Biological location:


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility4.3 g/LALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.9 m³·mol⁻¹ChemAxon
Polarizability20.58 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-2900000000-69c1daf79bf136cbeda8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03ki-9135400000-66bd27980748dec48932Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014j-0900000000-286fd6a398d981fb304bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004l-9500000000-e5d908b43c53fa144f04Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00or-9000000000-9c1d1b75d20954fa5e7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029b-0930000000-358780a634f9b76c8ffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ks-0900000000-a0c9e1c6055d07eff5fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abi-4900000000-98f74ecb570f22a3ab2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2590000000-950900f4d05879b38813Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bl-2910000000-04db11413f60bdfdb560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-5900000000-470f97906aa1018f9b73Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
      Not Available
UrineDetected and Quantified0.83-1.2 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
UrineDetected and Quantified0.75-0.93 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.0933 (0.00-0.187) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
UrineDetected and Quantified11.3 umol/mmol creatinineInfant (0-1 year old)Female
Aromatic L-amino acid decarboxylase deficiency
UrineDetected and Quantified12.7 umol/mmol creatinineChildren (1-13 years old)Female
Aromatic L-amino acid decarboxylase deficiency
Associated Disorders and Diseases
Disease References
Aromatic L-amino acid decarboxylase deficiency
  1. Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Associated OMIM IDs
  • 608643 (Aromatic L-amino acid decarboxylase deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022315
KNApSAcK IDNot Available
Chemspider ID141152
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound160637
PDB IDNot Available
ChEBI ID1240674
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceWong, Henry N. C.; Xu, Zun Le; Chang, Hson Mou; Lee, Chi Ming. Compounds from Danshen. 6. A modified synthesis of (±)-b-aryllactic acids. Synthesis (1992), (8), 793-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Javors MA, Bowden CL, Maas JW: 3-methoxy-4-hydroxyphenylglycol, 5-hydroxyindoleacetic acid, and homovanillic acid in human cerebrospinal fluid. Storage and measurement by reversed-phase high-performance liquid chromatography and coulometric detection using 3-methoxy-4-hydroxyphenyllactic acid as an internal standard. J Chromatogr. 1984 Dec 12;336(2):259-69. [PubMed:6085084 ]
  2. Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ]
  3. Ikeda H, Matsuyama S, Suzuki N, Takahashi A, Kuroiwa M: 3,4-dihydroxyphenylalanine (DOPA) decarboxylase deficiency and resultant high levels of plasma DOPA and dopamine in unfavorable neuroblastoma. Hypertens Res. 1995 Jun;18 Suppl 1:S209-10. [PubMed:8529065 ]
  4. Kinoshita Y, Yamada S, Haraguchi K, Takayanagi T, Mori Y, Takahashi T, Haruki E: Determination of vanillylmandelic acid, vanillactic acid, and homovanillic acid in dried urine on filter-paper discs by high-performance liquid chromatography with coulometric electrochemical detection for neuroblastoma screening. Clin Chem. 1988 Nov;34(11):2228-30. [PubMed:3180413 ]
  5. Muskiet FA, Fremouw-Ottevangers DC, van der Meulen J, Wolthers BG, de Vries JA: Determination of some L-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography. Clin Chem. 1978 Jan;24(1):122-7. [PubMed:73430 ]
  6. Jouve J, Bakri D, Herault J, Muh JP: Determination of urinary vanillactic acid and plasma dihydroxyphenylalanine as markers of non-secreting neuroblastoma by high-performance liquid chromatography with electrochemical detection. J Chromatogr. 1991 Jul 5;567(2):331-41. [PubMed:1939466 ]
  7. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10. [PubMed:1281049 ]
  8. Mashige F, Ohkubo A, Matsushima Y, Takano M, Tsuchiya E, Kanazawa H, Nagata Y, Takai N, Shinozuka N, Sakuma I: High-performance liquid chromatographic determination of catecholamine metabolites and 5-hydroxyindoleacetic acid in human urine using a mixed-mode column and an eight-channel electrode electrochemical detector. J Chromatogr B Biomed Appl. 1994 Aug 5;658(1):63-8. [PubMed:7524950 ]
  9. Tuchman M, Stoeckeler JS: Conjugated versus "free" acidic metabolites of catecholamines in random urine samples: significance for the diagnosis of neuroblastoma. Pediatr Res. 1988 Jun;23(6):576-9. [PubMed:3393388 ]
  10. Mashige F, Takai N, Matsushima Y, Ito A, Takano M, Tsuchiya E, Kanazawa H, Nagata Y, Shinozuka N, Wada H, et al.: [Simultaneous determination of catecholamines, serotonin, and their precursors and metabolites in body fluid by an HPLC system with multi-electrode electrochemical detector]. Rinsho Byori. 1994 Jun;42(6):591-9. [PubMed:7914240 ]
  11. Brautigam C, Hyland K, Wevers R, Sharma R, Wagner L, Stock GJ, Heitmann F, Hoffmann GF: Clinical and laboratory findings in twins with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency. Neuropediatrics. 2002 Jun;33(3):113-7. [PubMed:12200739 ]


General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
Uniprot ID:
Molecular weight:
Vanillactic acid → 3-(4-hydroxy-3-methoxyphenyl)-2-(sulfooxy)propanoic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
Uniprot ID:
Molecular weight:
Vanillactic acid → 6-[4-(2-carboxy-2-hydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Vanillactic acid → 3,4,5-trihydroxy-6-{[2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
Uniprot ID:
Molecular weight:
Vanillactic acid → 2-hydroxy-3-[3-methoxy-4-(sulfooxy)phenyl]propanoic aciddetails