AFCDB: Methyl benzoate (FDB012198)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:02 UTC

Update date

2020-09-17 15:35:28 UTC

Primary ID

FDB012198

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyl benzoate

Description

Methyl benzoate belongs to the class of organic compounds known as benzoic acid esters. Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the esterification of the carboxyl group in benzoic acid with methanol. It is a colorless to slightly yellow liquid that is immiscible with water but miscible with most organic solvents. Methyl benzoate is used as a flavouring agent. Methyl benzoate has been found in allspice, banana, cherry, pimento berry, ceriman (Monstera deliciosa), clove, mustard, coffee, black tea, dill, starfruit and cherimoya (Annona cherimola). It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study (PMID: 12647866).

CAS Number

93-58-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.75 g/L	ALOGPS
logP	1.98	ALOGPS
logP	1.98	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	38.08 m³·mol⁻¹	ChemAxon
Polarizability	14.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C8H8O2

IUPAC name

methyl benzoate

InChI Identifier

InChI=1S/C8H8O2/c1-10-8(9)7-5-3-2-4-6-7/h2-6H,1H3

InChI Key

QPJVMBTYPHYUOC-UHFFFAOYSA-N

Isomeric SMILES

COC(=O)C1=CC=CC=C1

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

Classification

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzoate ester (CHEBI:72775 )
an aromatic compound (CPD-6441 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Laboratory chemical

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 70.58%; H 5.92%; O 23.50%	DFC
Melting Point	Fp -12.3°	DFC
Boiling Point	Bp24 96-98°	DFC
Experimental Water Solubility	2.1 mg/mL at 20 oC	RIDDICK,JA et al. (1986)
Experimental logP	2.12	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	d2525 1.09	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-8900000000-5d1c26e3ea8cfe4bbf7a	2015-03-01	View Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4i-3900000000-c8e85f0df98caa46623c	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a6r-8900000000-6fca5a5a67e554be1310	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-e50a4550fe1c8b263d81	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-4dfb5ac01f5d5f7d5ce7	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-056r-9700000000-798ac6947aeb7428e12c	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4i-2900000000-158c47203ae5a78de7f1	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4r-2900000000-0d27c93c06f2d27bed8a	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a6r-9800000000-898ce08cbfefd77e3d38	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4i-3900000000-c8e85f0df98caa46623c	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a6r-8900000000-6fca5a5a67e554be1310	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a6r-6900000000-e50a4550fe1c8b263d81	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4i-5900000000-4dfb5ac01f5d5f7d5ce7	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-056r-9700000000-798ac6947aeb7428e12c	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4i-2900000000-158c47203ae5a78de7f1	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a4r-2900000000-0d27c93c06f2d27bed8a	Spectrum
GC-MS	Methyl benzoate, non-derivatized, GC-MS Spectrum	splash10-0a6r-9800000000-898ce08cbfefd77e3d38	Spectrum
Predicted GC-MS	Methyl benzoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-4900000000-7d64ee136952451331fe	Spectrum
Predicted GC-MS	Methyl benzoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-000i-0900000000-02cf79e13cdff713bc94	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-1900000000-46dc65ea3c3453f397af	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-2900000000-6d10d7854ba3eaad3821	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-000i-4900000000-dd1ab327a94aea1ffffa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000l-6900000000-b3d27912765863a6a3c7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000f-9800000000-6c6f95335e5013f73590	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-000f-9600000000-54956ed69705859e3745	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0006-9600000000-5cf0973d1485464fcbae	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-052f-9500000000-25ce0de1ba6505aa3ea2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-052f-9600000000-3864e43e7b74477d4d4c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0a4l-9600000000-8e38a89eae04d5e7984a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0a6u-9500000000-43fd82a420b27b47fd7a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-0a6s-9300000000-1d4f1e2d18e973fa4f40	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-b622c6657d31c63baa3b	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-a35e742379455d840bbf	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9500000000-040b49ccf596cdcb3158	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-04580a55e21379539e0c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-8a2984d01220ab172bdf	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-4900000000-6ccc7e9d5518bff71272	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-b622c6657d31c63baa3b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-a35e742379455d840bbf	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfr-9500000000-040b49ccf596cdcb3158	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-04580a55e21379539e0c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-8a2984d01220ab172bdf	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-4900000000-6ccc7e9d5518bff71272	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

External Links

ChemSpider ID

6883

ChEMBL ID

CHEMBL16435

KEGG Compound ID

Not Available

Pubchem Compound ID

7150

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33968

CRC / DFC (Dictionary of Food Compounds) ID

DVN38-Z:HFB52-B

EAFUS ID

2253

Dr. Duke ID

METHYL-BENZOATE|BENZOIC-ACID-METHYL-ESTER

BIGG ID

Not Available

KNApSAcK ID

C00034054

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

93-58-3

GoodScent ID

rw1015011

SuperScent ID

Not Available

Wikipedia ID

Methyl_benzoate

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
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
irritant			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
prune	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
lettuce	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
herb	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
wintergreen	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
almond	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cananga	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Methyl benzoate (FDB012198)

Structure for FDB012198 (Methyl benzoate)