Showing Compound Methoxybenzene (FDB012090)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:59 UTC

Update date

2015-07-20 22:46:51 UTC

Primary ID

FDB012090

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methoxybenzene

Description

Flavouring agent Anisole is a precursor to perfumes, insect pheromones, and pharmaceuticals. For example, synthetic anethole is prepared from anisole.; Anisole undergoes electrophilic aromatic substitution reaction more quickly than does benzene, which in turn reacts more quickly than nitrobenzene. The methoxy group is an ortho/para directing group, which means that electrophilic substitution preferentially occurs at these three sites. The enhanced nucleophilicity of anisole vs benzene reflects the influence of the methoxy group, which renders the ring more electron-rich. The methoxy group strongly affects the pi cloud of the ring, moreso than the inductive effect of the electronegative oxygen.

CAS Number

100-66-3

Structure

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

Synonyms

Synonym	Source
Anisol	ChEBI
Methoxybenzene	ChEBI
Methyl phenyl ether	ChEBI
Phenol methyl ether	ChEBI
Phenyl methyl ether	MeSH
Anisole, 8ci	HMDB
Anizol	HMDB
HSDB 44	HMDB
Methoxy-benzene	HMDB
Methoxy-benzene (anisol)	HMDB
Methyl phenyl-ether	HMDB
Phenoxymethane	HMDB
Anisole	biospider
Anisole [UN2222] [Flammable liquid]	biospider
Anisole, 8CI	db_source
Benzene, methoxy	biospider
Benzene, methoxy-	biospider
Ether, methyl phenyl	biospider
Ether, methyl phenyl-	biospider
FEMA 2097	db_source

Predicted Properties

Property	Value	Source
Water Solubility	3.14 g/L	ALOGPS
logP	2.1	ALOGPS
logP	1.82	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.52 m³·mol⁻¹	ChemAxon
Polarizability	11.8 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

C7H8O

IUPAC name

anisole

InChI Identifier

InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3

InChI Key

RDOXTESZEPMUJZ-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=CC=C1

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

Classification

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Methoxybenzene
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monomethoxybenzene (CHEBI:16579 )
a small molecule (CPD-395 )

Ontology

Disposition

Source:

Food

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 77.75%; H 7.46%; O 14.80%	DFC
Melting Point	Mp -37.5°	DFC
Boiling Point	Bp 155°	DFC
Experimental Water Solubility	1.04 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	2.11	HANSCH,C ET AL. (1995)
Experimental pKa	pKa -6.51 (H2SO4 aq.)	DFC
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	Methoxybenzene, non-derivatized, GC-MS Spectrum	splash10-0ar0-9300000000-9d7f6749c18da0bb17a5	Spectrum
GC-MS	Methoxybenzene, non-derivatized, GC-MS Spectrum	splash10-0ar0-9500000000-a1231ee8ae74f750d865	Spectrum
GC-MS	Methoxybenzene, non-derivatized, GC-MS Spectrum	splash10-0ar0-9300000000-03da541e1b0fc350901b	Spectrum
GC-MS	Methoxybenzene, non-derivatized, GC-MS Spectrum	splash10-0ar0-9300000000-9d7f6749c18da0bb17a5	Spectrum
GC-MS	Methoxybenzene, non-derivatized, GC-MS Spectrum	splash10-0ar0-9500000000-a1231ee8ae74f750d865	Spectrum
GC-MS	Methoxybenzene, non-derivatized, GC-MS Spectrum	splash10-0ar0-9300000000-03da541e1b0fc350901b	Spectrum
Predicted GC-MS	Methoxybenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9600000000-f06ab1867fa492dc70a4	Spectrum
Predicted GC-MS	Methoxybenzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methoxybenzene, 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	splash10-0a4i-0900000000-fb9a846e2f1273e85651	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-fd57d4e57fb46af8410b	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9100000000-af620e455f4ce9717299	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-ea0356f73dec1cbb2a6f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-8868de2e79fc0bfe5bb9	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9100000000-d3dbb7dea314eff0968f	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-5c0fe116caf5f5fa594c	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-9000000000-04348f17640621a98bf5	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-a9b5691a81bc9d478706	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-7900000000-2fb84cb3e84d8e17e508	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9000000000-4441fb8ba209a5f3d576	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16579

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33895

CRC / DFC (Dictionary of Food Compounds) ID

HDC34-O:HDC34-O

EAFUS ID

232

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1031451

SuperScent ID

7519

Wikipedia ID

Methoxybenzene

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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

Showing Compound Methoxybenzene (FDB012090)

Structure for FDB012090 (Methoxybenzene)