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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:56 UTC

Update Date

2023-02-21 17:22:33 UTC

HMDB ID

HMDB0032639

Secondary Accession Numbers

HMDB32639

Metabolite Identification

Common 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    5    7                                                       
CONECT    4    6    7                                                       
CONECT    5    3    8                                                       
CONECT    6    4    8                                                       
CONECT    7    3    4    9                                                  
CONECT    8    5    6   11                                                  
CONECT    9    7   10   12                                                  
CONECT   10    9                                                            
CONECT   11    1    8                                                       
CONECT   12    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	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

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

methyl 4-methoxybenzoate

Traditional Name

methyl anisate

CAS Registry Number

121-98-2

SMILES

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

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

Chemical Taxonomy

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

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032639)
Cytoplasm (HMDB: HMDB0032639)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032639)

Source

Endogenous

Endogenous (HMDB: HMDB0032639)

Plant

Plant (HMDB: HMDB0032639)

Exogenous

Food

Food (HMDB: HMDB0032639)

Herb and spice

Spice

Star anise (FooDB: FOOD00090)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0032639)
Flavoring Agent (HMDB: HMDB0032639)

Fragrance (HMDB: HMDB0032639)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	48 °C	Not Available
Boiling Point	244.00 to 245.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.64 mg/mL at 20 °C	Not Available
LogP	2.27	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.853	31661259
DarkChem	[M-H]-	137.428	31661259
DeepCCS	[M+H]+	136.766	30932474
DeepCCS	[M-H]-	133.499	30932474
DeepCCS	[M-2H]-	170.595	30932474
DeepCCS	[M+Na]+	146.134	30932474
AllCCS	[M+H]+	135.4	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	139.5	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	135.6	32859911
AllCCS	[M+Na-2H]-	136.7	32859911
AllCCS	[M+HCOO]-	138.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 4-methoxybenzoate	COC(=O)C1=CC=C(OC)C=C1	2098.6	Standard polar	33892256
Methyl 4-methoxybenzoate	COC(=O)C1=CC=C(OC)C=C1	1340.4	Standard non polar	33892256
Methyl 4-methoxybenzoate	COC(=O)C1=CC=C(OC)C=C1	1393.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)	splash10-014r-6900000000-ea0c740f9da9c4c70539	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)	splash10-000i-4900000000-d64fd9a65666e73ced8a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)	splash10-00kr-0900000000-3abbfda2a2e2a801ab8c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)	splash10-014r-6900000000-ea0c740f9da9c4c70539	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)	splash10-000i-4900000000-d64fd9a65666e73ced8a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl 4-methoxybenzoate EI-B (Non-derivatized)	splash10-00kr-0900000000-3abbfda2a2e2a801ab8c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 4-methoxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-2900000000-4554a3b4e1d463b0fd5e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 4-methoxybenzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Positive-QTOF	splash10-014i-0900000000-5d1c09395418f0c2133e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Positive-QTOF	splash10-014i-0900000000-90fdb37cd3a74b33d68c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Positive-QTOF	splash10-059i-3900000000-d89eddffdff84dcc594f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Negative-QTOF	splash10-014i-0900000000-69f4cc8bf456108754a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Negative-QTOF	splash10-014i-0900000000-ce81d76af8ef0abfc0fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Negative-QTOF	splash10-05n0-5900000000-1f91c2bab5730381aa5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Positive-QTOF	splash10-066r-0900000000-acee10ded01e8444992f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Positive-QTOF	splash10-052r-1900000000-b7caaa239ca1956148ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Positive-QTOF	splash10-114r-9400000000-0bbc122fec993ec92017	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 10V, Negative-QTOF	splash10-014i-0900000000-5dea0e2df5cd18252bf0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 20V, Negative-QTOF	splash10-0aor-0900000000-d21fad1db4d47d8572ad	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 4-methoxybenzoate 40V, Negative-QTOF	splash10-0btc-9100000000-f077fac91afffdb6eb74	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010588

KNApSAcK ID

C00030761

Chemspider ID

21108577

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8499

PDB ID

Not Available

ChEBI ID

86903

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032091

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl 4-methoxybenzoate (HMDB0032639)

MOL for HMDB0032639 (Methyl 4-methoxybenzoate)

3D MOL for HMDB0032639 (Methyl 4-methoxybenzoate)

3D SDF for HMDB0032639 (Methyl 4-methoxybenzoate)

3D-SDF for HMDB0032639 (Methyl 4-methoxybenzoate)

PDB for HMDB0032639 (Methyl 4-methoxybenzoate)

3D PDB for HMDB0032639 (Methyl 4-methoxybenzoate)

SMILES for HMDB0032639 (Methyl 4-methoxybenzoate)

INCHI for HMDB0032639 (Methyl 4-methoxybenzoate)

Structure for HMDB0032639 (Methyl 4-methoxybenzoate)

3D Structure for HMDB0032639 (Methyl 4-methoxybenzoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra