Record Information
Version1.0
Creation date2010-04-08 22:09:59 UTC
Update date2015-07-20 22:46:51 UTC
Primary IDFDB012090
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMethoxybenzene
DescriptionFlavouring 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 Number100-66-3
Structure
Thumb
Synonyms
SynonymSource
Anisolbiospider
Anisolebiospider
Anisole [UN2222] [Flammable liquid]biospider
Anisole, 8CIdb_source
Anizolbiospider
Benzene, methoxybiospider
Benzene, methoxy-biospider
Ether, methyl phenylbiospider
Ether, methyl phenyl-biospider
FEMA 2097db_source
HSDB 44biospider
Methoxy-benzeneHMDB
Methoxy-benzene (anisol)biospider
Methyl phenyl etherdb_source
Methyl phenyl-etherHMDB
Phenol methyl etherdb_source
Phenoxymethanebiospider
Phenyl methyl etherbiospider
Predicted Properties
PropertyValueSource
Water Solubility3.14 g/LALOGPS
logP2.1ALOGPS
logP1.82ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.52 m³·mol⁻¹ChemAxon
Polarizability11.8 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H8O
IUPAC nameanisole
InChI IdentifierInChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
InChI KeyInChIKey=RDOXTESZEPMUJZ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=CC=C1
Average Molecular Weight108
Monoisotopic Molecular Weight108
Classification
DescriptionThis compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenol ethers
Direct ParentAnisoles
Alternative Parents
Substituents
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 77.75%; H 7.46%; O 14.80%DFC
Melting PointMp -37.5°DFC
Boiling PointBp 155°DFC
Experimental Water Solubility1.04 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.11HANSCH,C ET AL. (1995)
Experimental pKapKa -6.51 (H2SO4 aq.)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ar0-9300000000-9d7f6749c18da0bb17a5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ar0-9500000000-a1231ee8ae74f750d865View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ar0-9300000000-03da541e1b0fc350901bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9600000000-f06ab1867fa492dc70a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-fb9a846e2f1273e85651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-fd57d4e57fb46af8410bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9100000000-af620e455f4ce9717299View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-ea0356f73dec1cbb2a6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-8868de2e79fc0bfe5bb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9100000000-d3dbb7dea314eff0968fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID7238
ChEMBL IDCHEMBL278024
KEGG Compound IDC01403
Pubchem Compound ID7519
Pubchem Substance IDNot Available
ChEBI ID16579
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33895
CRC / DFC (Dictionary of Food Compounds) IDHDC34-O:HDC34-O
EAFUS ID232
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1031451
SuperScent ID7519
Wikipedia IDMethoxybenzene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
butter
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cheese
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
alcohol
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
phenolic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
gasoline
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
anise
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference