Bovine Metabolome Database: Showing metabocard for Vanillic acid (BMDB0062211)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-07-17 17:17:57 UTC

Update Date

2020-04-22 15:51:34 UTC

BMDB ID

BMDB0062211

Secondary Accession Numbers

BMDB62211

Metabolite Identification

Common Name

Vanillic acid

Description

Vanillic acid, also known as vanillate or acid, vanillic, belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Vanillic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Vanillic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-Hydroxy-3-methoxybenzoic acid	ChEBI
4-Hydroxy-3-methoxybenzoate	Kegg
Vanillate	Generator
3-Methoxy-4-hydroxybenzoate	HMDB
3-Methoxy-4-hydroxybenzoic acid	HMDB
4-Hydroxy-3-methoxy-benzoate	HMDB
4-Hydroxy-3-methoxy-benzoic acid	HMDB
4-Hydroxy-m-anisate	HMDB
4-Hydroxy-m-anisic acid	HMDB
Acide vanillique	HMDB
p-Vanillate	HMDB
p-Vanillic acid	HMDB
Protocatechuic acid 3-methyl ester	HMDB
Acid, 4-hydroxy-3-methoxybenzoic	HMDB
p Hydroxy m methoxy benzoic acid	HMDB
4 Hydroxy 3 methoxybenzoic acid	HMDB
Acid, vanillic	HMDB
Acid, p-hydroxy-m-methoxy-benzoic	HMDB
p-Hydroxy-m-methoxy-benzoic acid	HMDB
2-Methoxy-4-carboxyphenol	HMDB
Methylprotocatechuic acid	HMDB
VA	HMDB
m-Methoxy-p-hydroxy-benzoic acid	HMDB
Vanillic acid	KEGG

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

IUPAC Name

4-hydroxy-3-methoxybenzoic acid

Traditional Name

vanillic acid

CAS Registry Number

121-34-6

SMILES

COC1=C(O)C=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

InChI Key

WKOLLVMJNQIZCI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

M-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:30816 )
methoxybenzoic acid (CHEBI:30816 )

Ontology

Status

Detected but not Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	211.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.5 mg/mL at 14 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	1.43	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.7	ALOGPS
logP	1.17	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.76 m³·mol⁻¹	ChemAxon
Polarizability	15.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28306241	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000484

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vanillic acid

METLIN ID

5471

PubChem Compound

8468

PDB ID

Not Available

ChEBI ID

30816

References

Synthesis Reference

Pearl, Irwin A. Reactions of vanillin and its derived compounds. I. The reaction of vanillin with silver oxide. Journal of the American Chemical Society (1946), 68 429-32.

Material Safety Data Sheet (MSDS)

Not Available

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Showing metabocard for Vanillic acid (BMDB0062211)

Structure for BMDB0062211 (Vanillic acid)