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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:40:09 UTC
Update Date2018-05-19 22:57:21 UTC
HMDB IDHMDB0033895
Secondary Accession Numbers
  • HMDB33895
Metabolite Identification
Common NameAnisole
DescriptionAnisole is a 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.
Structure
Thumb
Synonyms
ValueSource
AnisolChEBI
MethoxybenzeneChEBI
Methyl phenyl etherChEBI
Phenol methyl etherChEBI
Anisole, 8ciHMDB
AnizolHMDB
HSDB 44HMDB
Methoxy-benzeneHMDB
Methoxy-benzene (anisol)HMDB
Methyl phenyl-etherHMDB
PhenoxymethaneHMDB
Phenyl methyl etherHMDB
Chemical FormulaC7H8O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
IUPAC Nameanisole
Traditional Nameanisole
CAS Registry Number100-66-3
SMILES
COC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
InChI KeyRDOXTESZEPMUJZ-UHFFFAOYSA-N
Chemical Taxonomy
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-37.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.04 mg/mL at 25 °CNot Available
LogP2.11Not Available
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
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
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012090
KNApSAcK IDNot Available
Chemspider ID7238
KEGG Compound IDC01403
BioCyc IDCPD-395
BiGG IDNot Available
Wikipedia LinkAnisole
METLIN IDNot Available
PubChem Compound7519
PDB IDNot Available
ChEBI ID16579
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Dong XJ, Zhu YF, Bao GH, Hu FL, Qin GW: New limonoids and a dihydrobenzofuran norlignan from the roots of Toona sinensis. Molecules. 2013 Mar 1;18(3):2840-50. doi: 10.3390/molecules18032840. [PubMed:23455673 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .