Record Information
Version1.0
Creation date2010-04-08 22:10:09 UTC
Update date2020-09-17 15:35:07 UTC
Primary IDFDB012392
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Methoxy-4-(2-propenyl)benzene
DescriptionEstragole or 1-Methoxy-4-(2-propenyl) benzene, also known as methylchavicol, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Its chemical structure consists of a benzene ring substituted with a methoxy group and an allyl group. It is a colorless liquid, although impure samples can appear yellow. Estragole is a sweet, alcohol, and anise tasting compound. It is used in the preparation of fragrances. Estragole has also been found as a component of various trees and plants, including turpentine (pine oil), anise, fennel, bay, tarragon, and basil. It has also been found in lower concentrations in star anises, hyssops, and tarragons. Estragole has also been detected, but not quantified, in several different foods, such as ceylon cinnamons, dills, sweet bay, gingers, and pepper (spice).
CAS Number140-67-0
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.075 g/LALOGPS
logP3.23ALOGPS
logP2.91ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.81 m³·mol⁻¹ChemAxon
Polarizability16.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12O
IUPAC name1-methoxy-4-(prop-2-en-1-yl)benzene
InChI IdentifierInChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3
InChI KeyZFMSMUAANRJZFM-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(CC=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
  • 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:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-6900000000-67d45b594760b36935df2015-03-01View Spectrum
GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrumsplash10-0002-6900000000-8e0b04a96054353ba4d2Spectrum
GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrumsplash10-0002-5900000000-926e28a4944e333f20a8Spectrum
GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrumsplash10-0002-3900000000-fcf899888322560675f8Spectrum
GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrumsplash10-0002-6900000000-8e0b04a96054353ba4d2Spectrum
GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrumsplash10-0002-5900000000-926e28a4944e333f20a8Spectrum
GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrumsplash10-0002-3900000000-fcf899888322560675f8Spectrum
Predicted GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05cs-3900000000-15f67266c369bb73d449Spectrum
Predicted GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-9300000000-ed4cfbbd9e08d2cee0ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0900000000-3765ce70f44412b9c2022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0900000000-e86d0a9f461d702ad87d2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-6115b055d0ac87df694e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-8be4c2f5dd1b59c563a82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyl-9800000000-da4984de313826c7d3252016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-590e344336c3b35d97382016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-85e1e245e010ba27ce2a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3900000000-c9c3734a65e1844d72762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-1900000000-3370bab5911072db0adf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-5900000000-2c944ec1b9ce38d95a4e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-23d4baf27aa3941828a22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-7512c83d9a8de7a2b2bb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-fe719bda7b98ff0571f72021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
ChemSpider ID13850247
ChEMBL IDCHEMBL470671
KEGG Compound IDC10452
Pubchem Compound ID8815
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID649
DrugBank IDNot Available
HMDB IDHMDB34121
CRC / DFC (Dictionary of Food Compounds) IDHGQ74-N:HGS47-R
EAFUS ID1117
Dr. Duke IDCHAVICOL-METHYL-ETHER|METHYL-CHAVICOL|ESTRAGOLE
BIGG IDNot Available
KNApSAcK IDC00002740
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID140-67-0
GoodScent IDrw1013251
SuperScent ID8815
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— 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.