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1-Methoxy-4-(2-propenyl)benzene (FDB012392)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 81.04%; H 8.16%; O 10.80%DFC
Melting PointNot Available
Boiling PointBp16 102°DFC
Experimental Water Solubility0.178 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd15 0.98DFC
Refractive Indexn27D 1.5230DFC
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
DNA-binderDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hepatocarcinogenic50903 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.DUKE
hypothermicDUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
mutagenicDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
licorice
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
anise
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  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
minty
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sassafrass
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fennel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.