Showing Compound Methyl 4-methoxybenzoate (FDB010588)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:12 UTC

Update date

2019-11-26 03:03:52 UTC

Primary ID

FDB010588

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyl 4-methoxybenzoate

Description

Methyl 4-methoxybenzoate, also known as 4-methoxy methylbenzoate or methyl 4-anisate, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. Methyl 4-methoxybenzoate is a sweet, anise, and balsam tasting compound. Methyl 4-methoxybenzoate is found, on average, in the highest concentration within star anises (Illicium verum). This could make methyl 4-methoxybenzoate a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Methyl 4-methoxybenzoate.

CAS Number

121-98-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-Methoxy methylbenzoate	ChEBI
Methyl 4-anisate	ChEBI
p-Methoxybenzoic acid methyl ester	ChEBI
4-Methoxy methylbenzoic acid	Generator
Methyl 4-anisic acid	Generator
p-Methoxybenzoate methyl ester	Generator
Methyl 4-methoxybenzoic acid	Generator
4-Methoxybenzoic acid methyl ester	HMDB
Benzoic acid, 4-methoxy-, methyl ester	HMDB
Benzoic acid, P-methoxy-, methyl ester	HMDB
FEMA 2679	HMDB
Methyl ester OF P-methoxybenzoic acid	HMDB
Methyl P-anisate	HMDB, MeSH
Methyl P-methoxybenzoate	HMDB
P-Anisic acid methyl ester	HMDB
P-Anisic acid, methyl ester	HMDB
Methyl p-anisic acid	Generator
4-methoxy methylbenzoate	biospider
Benzoic acid, p-methoxy-, methyl ester	biospider
Methyl 4-methoxybenzoate	db_source
Methyl ester of p-methoxybenzoic acid	biospider
Methyl p-anisate	db_source
Methyl p-methoxybenzoate	biospider
P-anisic acid methyl ester	biospider
P-anisic acid, methyl ester	biospider
P-methoxybenzoic acid methyl ester	biospider

Predicted Properties

Property	Value	Source
Water Solubility	1.37 g/L	ALOGPS
logP	2.05	ALOGPS
logP	1.82	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.55 m³·mol⁻¹	ChemAxon
Polarizability	17.21 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	No	ChemAxon

Chemical Formula

C9H10O3

IUPAC name

methyl 4-methoxybenzoate

InChI Identifier

InChI=1S/C9H10O3/c1-11-8-5-3-7(4-6-8)9(10)12-2/h3-6H,1-2H3

InChI Key

DDIZAANNODHTRB-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

Classification

Description

Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 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

P-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-methoxybenzoic acid or derivatives
Benzoate ester
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
Alkyl aryl ether
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monomethoxybenzene (CHEBI:86903 )
benzoate ester (CHEBI:86903 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 65.05%; H 6.07%; O 28.88%	DFC
Melting Point	Mp 48°	DFC
Boiling Point	Bp20 160°	DFC
Experimental Water Solubility	0.643 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.27	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Methyl 4-methoxybenzoate, non-derivatized, GC-MS Spectrum	splash10-014r-6900000000-ea0c740f9da9c4c70539	Spectrum
GC-MS	Methyl 4-methoxybenzoate, non-derivatized, GC-MS Spectrum	splash10-000i-4900000000-d64fd9a65666e73ced8a	Spectrum
GC-MS	Methyl 4-methoxybenzoate, non-derivatized, GC-MS Spectrum	splash10-00kr-0900000000-3abbfda2a2e2a801ab8c	Spectrum
GC-MS	Methyl 4-methoxybenzoate, non-derivatized, GC-MS Spectrum	splash10-014r-6900000000-ea0c740f9da9c4c70539	Spectrum
GC-MS	Methyl 4-methoxybenzoate, non-derivatized, GC-MS Spectrum	splash10-000i-4900000000-d64fd9a65666e73ced8a	Spectrum
GC-MS	Methyl 4-methoxybenzoate, non-derivatized, GC-MS Spectrum	splash10-00kr-0900000000-3abbfda2a2e2a801ab8c	Spectrum
Predicted GC-MS	Methyl 4-methoxybenzoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052r-2900000000-4554a3b4e1d463b0fd5e	Spectrum
Predicted GC-MS	Methyl 4-methoxybenzoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-5d1c09395418f0c2133e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-90fdb37cd3a74b33d68c	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059i-3900000000-d89eddffdff84dcc594f	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-69f4cc8bf456108754a4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-ce81d76af8ef0abfc0fd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05n0-5900000000-1f91c2bab5730381aa5b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-066r-0900000000-acee10ded01e8444992f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-1900000000-b7caaa239ca1956148ef	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-114r-9400000000-0bbc122fec993ec92017	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-5dea0e2df5cd18252bf0	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-0900000000-d21fad1db4d47d8572ad	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9100000000-f077fac91afffdb6eb74	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

21108577

ChEMBL ID

CHEMBL1762668

KEGG Compound ID

Not Available

Pubchem Compound ID

8499

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB32639

CRC / DFC (Dictionary of Food Compounds) ID

FFR17-A:FFR18-B

EAFUS ID

2247

Dr. Duke ID

METHYL-ANISATE

BIGG ID

Not Available

KNApSAcK ID

C00030761

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1032091

SuperScent ID

8499

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Name	48318	flavor	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
anise	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
melon	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.