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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:40:09 UTC
Update Date2022-03-07 02:53:53 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
Data?1563862477
Synonyms
ValueSource
AnisolChEBI
MethoxybenzeneChEBI
Methyl phenyl etherChEBI
Phenol methyl etherChEBI
Phenyl methyl etherMeSH
Anisole, 8ciHMDB
AnizolHMDB
HSDB 44HMDB
Methoxy-benzeneHMDB
Methoxy-benzene (anisol)HMDB
Methyl phenyl-etherHMDB
PhenoxymethaneHMDB
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
Description 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
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-37.5 °CNot Available
Boiling Point153.00 to 155.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.04 mg/mL at 25 °CNot Available
LogP2.11Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.67231661259
DarkChem[M-H]-118.85731661259
DeepCCS[M+H]+122.53330932474
DeepCCS[M-H]-119.89730932474
DeepCCS[M-2H]-156.2730932474
DeepCCS[M+Na]+130.92430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AnisoleCOC1=CC=CC=C11293.4Standard polar33892256
AnisoleCOC1=CC=CC=C1898.8Standard non polar33892256
AnisoleCOC1=CC=CC=C1914.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Anisole EI-B (Non-derivatized)splash10-0ar0-9300000000-9d7f6749c18da0bb17a52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anisole EI-B (Non-derivatized)splash10-0ar0-9500000000-a1231ee8ae74f750d8652017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anisole EI-B (Non-derivatized)splash10-0ar0-9300000000-03da541e1b0fc350901b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anisole EI-B (Non-derivatized)splash10-0ar0-9300000000-9d7f6749c18da0bb17a52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anisole EI-B (Non-derivatized)splash10-0ar0-9500000000-a1231ee8ae74f750d8652018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Anisole EI-B (Non-derivatized)splash10-0ar0-9300000000-03da541e1b0fc350901b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anisole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9600000000-f06ab1867fa492dc70a42016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anisole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Anisole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 10V, Positive-QTOFsplash10-0a4i-0900000000-fb9a846e2f1273e856512015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 20V, Positive-QTOFsplash10-0a4i-0900000000-fd57d4e57fb46af8410b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 40V, Positive-QTOFsplash10-0ufr-9100000000-af620e455f4ce97172992015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 10V, Negative-QTOFsplash10-0a4i-0900000000-ea0356f73dec1cbb2a6f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 20V, Negative-QTOFsplash10-0a4i-0900000000-8868de2e79fc0bfe5bb92015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 40V, Negative-QTOFsplash10-056r-9100000000-d3dbb7dea314eff0968f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 10V, Negative-QTOFsplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 20V, Negative-QTOFsplash10-0a4i-2900000000-5c0fe116caf5f5fa594c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 40V, Negative-QTOFsplash10-01t9-9000000000-04348f17640621a98bf52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 10V, Positive-QTOFsplash10-0a4i-0900000000-a9b5691a81bc9d4787062021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 20V, Positive-QTOFsplash10-0a4i-7900000000-2fb84cb3e84d8e17e5082021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Anisole 40V, Positive-QTOFsplash10-004i-9000000000-4441fb8ba209a5f3d5762021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB012090
KNApSAcK IDC00052810
Chemspider ID7238
KEGG Compound IDC01403
BioCyc IDCPD-395
BiGG IDNot Available
Wikipedia LinkAnisole
METLIN IDNot Available
PubChem Compound7519
PDB IDNot Available
ChEBI ID16579
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031451
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.. .