Record Information
Version1.0
Creation date2010-04-08 22:05:31 UTC
Update date2020-09-17 15:36:19 UTC
Primary IDFDB002793
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAnethole
DescriptionAnethole or 1-Methoxy-4(1-propenyl)-benzene, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anethole is an extremely weak basic (essentially neutral) compound (based on its pKa). Anethol is a naturally occurring organic compound found in the essential oils of many plants such as anise, fennel, anise myrtle, liquorice as their large component of the odor and flavor. Anethole is a sweet, anise, and balsam tasting compound. It is used as a flavoring agent in alcoholic drinks and in small quantities in natural berry flavors. Anethole is found in a lower concentration in peppermints, wild celeries, and corianders. Anethole has also been detected, but not quantified in, several different foods, such as nutmegs, cumins, lemon balms, common thymes, and herbs and spices. This could make anethole a potential biomarker for the consumption of these foods. Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977, 17078111, 18944489). There are two known anethol isomers including Cis- and Trans-anethol.
CAS Number4180-23-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP3.4ALOGPS
logP2.94ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.88 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12O
IUPAC name1-methoxy-4-[(1Z)-prop-1-en-1-yl]benzene
InChI IdentifierInChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3-
InChI KeyRUVINXPYWBROJD-ARJAWSKDSA-N
Isomeric SMILESCOC1=CC=C(\C=C/C)C=C1
Average Molecular Weight148.2017
Monoisotopic Molecular Weight148.088815006
Classification
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
  • Styrene
  • 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

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAnethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-2900000000-0665985a70ac9c27eb53Spectrum
Predicted GC-MSAnethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-436711faeb648ff2a2d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-7d9dfbe23492f9be6a292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9600000000-582716ef7e52a802bbc12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e66c5cd440af8e6d0c882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-709cb24546c67c386dde2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3900000000-ecda3d7970e587876f662016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5aa2093882ee9ccdc8862021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-03b30da0f9adb9d580ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-d856cd34f2f6f83def662021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-2900000000-b32a050861e7a927efa52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-e059cbeab65dc16bd3b42021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID637563
Pubchem Substance IDNot Available
ChEBI ID35616
Phenol-Explorer ID645
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHBT07-B:CNR12-S
EAFUS ID213
Dr. Duke IDANETHOL|ANETHOLE|TRANS-ANETHOLE
BIGG IDNot Available
KNApSAcK IDC00029334
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1001151
SuperScent ID637563
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
AllspiceExpected but not quantifiedNot AvailableDUKE
Anise3400.000 - 9800.000 mg/100 g6600.000 mg/100 gDUKE, KNAPSACK
AvocadoExpected but not quantifiedNot AvailableDUKE
Common oreganoExpected but not quantifiedNot AvailableDUKE
Common thymeExpected but not quantifiedNot AvailableDUKE
Coriander0.15000 - 0.15000 mg/100 g0.15000 mg/100 gDUKE
Dill27.550 - 27.550 27.550 DUKE
Fennel1.971 - 3800.500 mg/100 g1452.490 mg/100 gPHENOL EXPLORER, DUKE, KNAPSACK
Lemon balmExpected but not quantifiedNot AvailableDUKE
LovageExpected but not quantifiedNot AvailableDUKE
Showing 1 to 10 of 18 entries
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.