Showing Compound Card for Estragole (CDB000600)

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Record Information
Version1.0
Created at2020-03-19 00:45:56 UTC
Updated at2020-12-07 19:07:34 UTC
CannabisDB IDCDB000600
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEstragole
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). Estragole has also been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
MethylchavicolKegg
4-AllylanisoleMeSH
Methyl chavicolMeSH
p-AllylanisoleMeSH
1-Allyl-4-methoxybenzeneHMDB
1-Methoxy-4-(2-propen-1-yl)-benzeneHMDB
1-Methoxy-4-(2-propen-1-yl)benzeneHMDB
1-Methoxy-4-(2-propenyl)-benzeneHMDB
1-Methoxy-4-(2-propenyl)benzene, 9ciHMDB
1-Methoxy-4-prop-2-enylbenzeneHMDB
3-(p-Methoxyphenyl)propeneHMDB
4-Allyl-1-methoxybenzeneHMDB
4-AllylmethoxybenzeneHMDB
4-MethoxyallylbenzeneHMDB
Benzene, 1-methoxy, 4-prop-2-enylHMDB
BENZENE,1-allyl,4-methoxy methylchavicolHMDB
Chavicol methyl etherHMDB
Chavicyl methyl etherHMDB
EsdragolHMDB
EsdragoleHMDB
EsdragonHMDB
EstragolHMDB
Estragol (methylchavicol)HMDB
EstragoleHMDB
Ether, P-allylphenyl methylHMDB
FEMA 2411HMDB
IsoanetholeHMDB
IsoanthetholeHMDB
Methyl chavicoleHMDB
Methyl chavicole (estragole)HMDB
Methyl-chavicolHMDB
O-Methyl-chavicolHMDB
P-Allyl-anisoleHMDB
P-AllylmethoxybenzeneHMDB
p-Allylphenyl methyl etherHMDB
p-MethoxyallylbenzeneHMDB
Para-allylanisole (estragole)HMDB
TarragonHMDB
TerragonHMDB
1-Methoxy-4-(2-propenyl)benzeneKEGG
3-(4-Methoxyphenyl)-1-propenePhytoBank
3-(4-Methoxyphenyl)propenePhytoBank
3-(p-Methoxyphenyl)-1-propenePhytoBank
EsteragolPhytoBank
EstragenolePhytoBank
O-MethylchavicolPhytoBank
Chemical FormulaC10H12O
Average Molecular Weight148.2
Monoisotopic Molecular Weight148.0888
IUPAC Name1-methoxy-4-(prop-2-en-1-yl)benzene
Traditional Nametarragon
CAS Registry Number140-67-0
SMILES
COC1=CC=C(CC=C)C=C1
InChI Identifier
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3
InChI KeyZFMSMUAANRJZFM-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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point216 °CWikipedia
Water Solubility0.18 mg/mL at 25 °CNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-6900000000-67d45b594760b36935df2015-03-01View Spectrum
GC-MSEstragole, non-derivatized, GC-MS Spectrumsplash10-0002-6900000000-8e0b04a96054353ba4d2Spectrum
GC-MSEstragole, non-derivatized, GC-MS Spectrumsplash10-0002-5900000000-926e28a4944e333f20a8Spectrum
GC-MSEstragole, non-derivatized, GC-MS Spectrumsplash10-0002-3900000000-fcf899888322560675f8Spectrum
GC-MSEstragole, non-derivatized, GC-MS Spectrumsplash10-0002-6900000000-8e0b04a96054353ba4d2Spectrum
GC-MSEstragole, non-derivatized, GC-MS Spectrumsplash10-0002-5900000000-926e28a4944e333f20a8Spectrum
GC-MSEstragole, non-derivatized, GC-MS Spectrumsplash10-0002-3900000000-fcf899888322560675f8Spectrum
Predicted GC-MSEstragole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05cs-3900000000-15f67266c369bb73d449Spectrum
Predicted GC-MSEstragole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEstragole, 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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034121
DrugBank IDNot Available
Phenol Explorer Compound ID649
FoodDB IDFDB012392
KNApSAcK IDC00002740
Chemspider ID13850247
KEGG Compound IDC10452
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8815
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]