FComEx: Vanillic acid (PC000439)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:43 UTC

Update date

2017-01-19 02:36:24 UTC

FoodComEx ID

PC000439

FoodDB Record

FDB000846

Chemical Information

Name

Vanillic acid

Description

Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5'nucleotidase activity. (PMID: 16899266).

CAS Number

121-34-6

Structure

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

Synonyms

Synonym	Source
3-Methoxy-4-hydroxybenzoate	biospider
3-Methoxy-4-hydroxybenzoic acid	biospider
4 Hydroxy 3 methoxybenzoic Acid	biospider
4-hydroxy-3-methoxy-Benzoate	biospider
4-hydroxy-3-methoxy-Benzoic acid	biospider
4-Hydroxy-3-methoxybenzoate	Generator
4-Hydroxy-3-methoxybenzoic acid	db_source
4-Hydroxy-3-methoxybenzoic acid (vanillic acid)	biospider
4-hydroxy-m-Anisate	biospider
4-hydroxy-m-Anisic acid	biospider
Acid, 4-Hydroxy-3-methoxybenzoic	biospider
Acid, p-hydroxy-m-methoxy-benzoic	biospider
Acid, vanillic	biospider
Acide vanillique	HMDB
Benzoic acid, 4-hydroxy-3-methoxy-	biospider
m-Anisic acid, 4-hydroxy-	biospider
P hydroxy m methoxy benzoic acid	biospider
P-hydroxy-m-methoxy-benzoic acid	biospider
P-hydroxy-m-methoxy-benzonic acid	biospider
P-vanillate	biospider
P-vanillic acid	biospider
Protocatechuic acid 3-methyl ester	biospider
Protocatechuic acid, 3-methyl ester	biospider
VA	biospider
Va (van)	biospider
Vanillate	Generator
Vanillic acid	db_source
VNL	biospider

Chemical Formula

C8H8O4

IUPAC name

4-hydroxy-3-methoxybenzoic acid

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

Isomeric SMILES

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

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

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 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	1.43	HANSCH,C ET AL. (1995)
Experimental Water Solubility	1.5 mg/mL at 14 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 210°	DFC

Foods of Origin