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
SynonymSource
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
1-Methoxy-4-(2-propenyl)benzene, 9CIdb_source
1-methoxy-4-prop-2-enylbenzenebiospider
Allylphenyl methyl ether, p-biospider
Anisole, p-allyl-biospider
Benzene, 1-methoxy-4-(2-propen-1-yl)-biospider
Benzene, 1-methoxy-4-(2-propenyl)-biospider
p-Allylmethoxybenzenebiospider
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
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-aggregantAn agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Carcinogenic50903 An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.DUKE
DNA-binderAn agent that binds to DNA, regulating gene expression and replication. It has therapeutic applications in gene therapy, cancer treatment, and antimicrobial therapy, with key medical uses including targeting viral DNA and modulating immune responses.DUKE
Name48318 flavorDUKE
Hepatocarcinogenic50903 An agent that promotes the development of liver cancer, having a harmful biological role. It has no therapeutic applications, but understanding its effects is crucial in liver cancer research and prevention. Key medical uses include studying liver carcinogenesis and developing strategies to mitigate its harmful effects.DUKE
HypothermicA condition of abnormally low body temperature, playing a biological role in reducing metabolic rate and oxygen demand. Therapeutically, it has applications in neuroprotection, cardiac surgery, and trauma care. Key medical uses include treating heatstroke, cardiac arrest, and brain injuries, as well as preserving organs for transplantation.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Perfumery48318 The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.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.