ContaminantDB: Vanillactic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:36:43 UTC

Update Date

2026-04-06 13:09:12 UTC

Accession Number

CHEM003335

Identification

Common Name

Vanillactic acid

Class

Small Molecule

Description

Vanillactic acid is an acidic catecholamine metabolite present in normal human urine , in normal human CSF , and increased in the CSF of newborns with neonatal epileptic encephalopathy mimicking aromatic L-amino acid decarboxylase deficiency (3, 4, 5).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Animal Toxin
Ether
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vanillactate	Generator
3-(3-Methoxy-4-hydroxyphenyl)lactate	HMDB
3-(3-Methoxy-4-hydroxyphenyl)lactic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-lactate	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-lactic acid	HMDB
3-(4-Hydroxy-3-methoxyphenyl)lactate	HMDB
3-(4-Hydroxy-3-methoxyphenyl)lactic acid	HMDB
3-Methoxy-4-hydroxyphenyllactate	HMDB
3-Methoxy-4-hydroxyphenyllactic acid	HMDB
4-Hydroxy-3-methoxyphenyllactic acid	HMDB
b-(4-Hydroxy-3-methoxyphenyl)lactate	HMDB
b-(4-Hydroxy-3-methoxyphenyl)lactic acid	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)lactate	HMDB
beta-(4-Hydroxy-3-methoxyphenyl)lactic acid	HMDB
Vanillyllactate	HMDB
Vanillyllactic acid	HMDB
VLA	HMDB
Vanillylactic acid	HMDB
2-Hydroxy-3-(4-hydroxy-3-methoxyphenyl)propanoate	HMDB
Vanillactic acid	MeSH

Chemical Formula

C₁₀H₁₂O₅

Average Molecular Mass

212.199 g/mol

Monoisotopic Mass

212.068 g/mol

CAS Registry Number

2475-56-1

IUPAC Name

Not Available

Traditional Name

vanillactic acid

SMILES

COC1=CC(CC(O)C(O)=O)=CC=C1O

InChI Identifier

InChI=1S/C10H12O5/c1-15-9-5-6(2-3-7(9)11)4-8(12)10(13)14/h2-3,5,8,11-12H,4H2,1H3,(H,13,14)

InChI Key

SVYIZYRTOYHQRE-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-11831 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Hawkinsinuria	SMP00190	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.3 g/L	ALOGPS
logP	1.08	ALOGPS
logP	0.72	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.9 m³·mol⁻¹	ChemAxon
Polarizability	20.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ku-2900000000-69c1daf79bf136cbeda8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-03ki-9135400000-66bd27980748dec48932	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014j-0900000000-286fd6a398d981fb304b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004l-9500000000-e5d908b43c53fa144f04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00or-9000000000-9c1d1b75d20954fa5e7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-029b-0930000000-358780a634f9b76c8ffd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00ks-0900000000-a0c9e1c6055d07eff5fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0abi-4900000000-98f74ecb570f22a3ab2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2590000000-950900f4d05879b38813	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01bl-2910000000-04db11413f60bdfdb560	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dr-5900000000-470f97906aa1018f9b73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03fr-9480000000-528dd14b88a108965ec9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g0-5900000000-4c7476268c7a3c11a131	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-3930000000-2725f9ff3e03c2076f86	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03ds-0950000000-178e1e266b1f63c6ec8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-95be65594bf90008ecaa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kr-9800000000-46f5d9fc7bb2d38b6766	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000913

FooDB ID

FDB022315

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5868

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

141152

ChEBI ID

1240674

PubChem Compound ID

160637

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Wong, 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.

MSDS

Not Available

General References

1. Wong, 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

8. Hyland K, Clayton PT: Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10.

9. 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.

10. 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.

11. 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.

12. 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.

Vanillactic acid (CHEM003335)

Structure for CHEM003335: Vanillactic acid