ChemFOnt: Showing chemical card for Methyl vanillate (CFc000220530)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 01:39:41 UTC

Chemfont ID

CFc000220530

Molecule Identification

Common Name

Methyl vanillate

Definition

Methyl vanillate is a member of the class of compounds known as m-methoxybenzoic acids and derivatives. These compounds are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Methyl vanillate is considered to be a slightly soluble in water acidic compound. Methyl vanillate can be synthesized from vanillic acid. Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. Vanillic acid is also found in wine and vinegar. Vanillic acid is a metabolic by-product of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'-nucleotidase activity (PMID:16899266 ). Vanillic acid is also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID:11152072 , 10543794 , 11728709 , 9579070 ). Methyl vanillate has been identified in foods such as cow's milk (PMID:4682334 ) and beer (PMID:20800742 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Hydroxy-3-methoxybenzoic acid methyl ester	ChEBI
Methyl 3-methoxy-4-hydroxybenzoate	ChEBI
Methyl vanillic acid	ChEBI
VANILLATE	ChEBI
Vanillic acid, methyl ester	ChEBI
4-Hydroxy-3-methoxybenzoate methyl ester	Generator
Methyl 3-methoxy-4-hydroxybenzoic acid	Generator
VANILLic acid	Generator
Vanillate, methyl ester	Generator
Methylvanillate	HMDB
Methylvanillic acid	HMDB
Methyl 4-hydroxy-3-methoxybenzoic acid	HMDB
4-Hydroxy-3-methoxy methyl benzoate	HMDB
Methyl 4-hydroxy-3-methoxybenzoate	HMDB
4-Hydroxy-3-methoxy methyl benzoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

vanillate

CAS Registry Number

3943-74-6

SMILES

COC(=O)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3

InChI Key

BVWTXUYLKBHMOX-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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:46477 )
phenols (CHEBI:46477 )
benzoate ester (CHEBI:46477 )

Functional Ontology

Exogenous (HMDB: HMDB0240266)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.57 g/L	ALOGPS
logP	2.12	ALOGPS
logP	1.52	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.53 m³·mol⁻¹	ChemAxon
Polarizability	18.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon