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

Record Information

Version

1.0

Creation date

2010-04-08 22:10:09 UTC

Update date

2020-09-17 15:35:07 UTC

Primary ID

FDB012392

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

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

Description

Estragole 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 Number

140-67-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Methylchavicol	Kegg
4-Allylanisole	MeSH
Methyl chavicol	MeSH
p-Allylanisole	MeSH
1-Allyl-4-methoxybenzene	HMDB
1-Methoxy-4-(2-propen-1-yl)-benzene	HMDB
1-Methoxy-4-(2-propen-1-yl)benzene	HMDB
1-Methoxy-4-(2-propenyl)-benzene	HMDB
1-Methoxy-4-(2-propenyl)benzene, 9ci	HMDB
1-Methoxy-4-prop-2-enylbenzene	HMDB
3-(p-Methoxyphenyl)propene	HMDB
4-Allyl-1-methoxybenzene	HMDB
4-Allylmethoxybenzene	HMDB
4-Methoxyallylbenzene	HMDB
Benzene, 1-methoxy, 4-prop-2-enyl	HMDB
BENZENE,1-allyl,4-methoxy methylchavicol	HMDB
Chavicol methyl ether	HMDB
Chavicyl methyl ether	HMDB
Esdragol	HMDB
Esdragole	HMDB
Esdragon	HMDB
Estragol	HMDB
Estragol (methylchavicol)	HMDB
Estragole	HMDB
Ether, P-allylphenyl methyl	HMDB
FEMA 2411	HMDB
Isoanethole	HMDB
Isoanthethole	HMDB
Methyl chavicole	HMDB
Methyl chavicole (estragole)	HMDB
Methyl-chavicol	HMDB
O-Methyl-chavicol	HMDB
P-Allyl-anisole	HMDB
P-Allylmethoxybenzene	HMDB
p-Allylphenyl methyl ether	HMDB
p-Methoxyallylbenzene	HMDB
Para-allylanisole (estragole)	HMDB
Tarragon	HMDB
Terragon	HMDB
1-Methoxy-4-(2-propenyl)benzene	KEGG
3-(4-Methoxyphenyl)-1-propene	PhytoBank
3-(4-Methoxyphenyl)propene	PhytoBank
3-(p-Methoxyphenyl)-1-propene	PhytoBank
Esteragol	PhytoBank
Estragenole	PhytoBank
O-Methylchavicol	PhytoBank
1-Methoxy-4-(2-propenyl)benzene, 9CI	db_source
1-methoxy-4-prop-2-enylbenzene	biospider
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-Allylmethoxybenzene	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.075 g/L	ALOGPS
logP	3.23	ALOGPS
logP	2.91	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.81 m³·mol⁻¹	ChemAxon
Polarizability	16.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12O

IUPAC name

1-methoxy-4-(prop-2-en-1-yl)benzene

InChI Identifier

InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3

InChI Key

ZFMSMUAANRJZFM-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(CC=C)C=C1

Average Molecular Weight

148.2017

Monoisotopic Molecular Weight

148.088815006

Classification

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

olefinic compound (CHEBI:4867 )
Monolignols (C10452 )
an aromatic compound (CPD-6484 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 81.04%; H 8.16%; O 10.80%	DFC
Melting Point	Not Available
Boiling Point	Bp16 102°	DFC
Experimental Water Solubility	0.178 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d15 0.98	DFC
Refractive Index	n27D 1.5230	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0002-6900000000-67d45b594760b36935df	2015-03-01	View Spectrum
GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum	splash10-0002-6900000000-8e0b04a96054353ba4d2	Spectrum
GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum	splash10-0002-5900000000-926e28a4944e333f20a8	Spectrum
GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum	splash10-0002-3900000000-fcf899888322560675f8	Spectrum
GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum	splash10-0002-6900000000-8e0b04a96054353ba4d2	Spectrum
GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum	splash10-0002-5900000000-926e28a4944e333f20a8	Spectrum
GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, GC-MS Spectrum	splash10-0002-3900000000-fcf899888322560675f8	Spectrum
Predicted GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05cs-3900000000-15f67266c369bb73d449	Spectrum
Predicted GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1-Methoxy-4-(2-propenyl)benzene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-9300000000-ed4cfbbd9e08d2cee0ad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0900000000-3765ce70f44412b9c202	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-0900000000-e86d0a9f461d702ad87d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-6115b055d0ac87df694e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-2900000000-8be4c2f5dd1b59c563a8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uyl-9800000000-da4984de313826c7d325	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-590e344336c3b35d9738	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-85e1e245e010ba27ce2a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3900000000-c9c3734a65e1844d7276	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dj-1900000000-3370bab5911072db0adf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dm-5900000000-2c944ec1b9ce38d95a4e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9100000000-23d4baf27aa3941828a2	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-c2f74e33d816bec66aa0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-7512c83d9a8de7a2b2bb	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-2900000000-fe719bda7b98ff0571f7	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

649

DrugBank ID

Not Available

HMDB ID

HMDB34121

CRC / DFC (Dictionary of Food Compounds) ID

HGQ74-N:HGS47-R

EAFUS ID

1117

Dr. Duke ID

CHAVICOL-METHYL-ETHER|METHYL-CHAVICOL|ESTRAGOLE

BIGG ID

Not Available

KNApSAcK ID

C00002740

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

140-67-0

GoodScent ID

rw1013251

SuperScent ID

8815

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti-aggregant		An 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 antagonist	48706	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 preventive	35610	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
Carcinogenic	50903	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-binder		An 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
Name	48318	flavor	DUKE
Hepatocarcinogenic	50903	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
Hypothermic		A 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
Insecticide	24852	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
Insectifuge	24852	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
Mutagenic		An 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
Perfumery	48318	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
Pesticide	25944	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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
licorice	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	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
alcohol	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
minty	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sassafrass	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fennel	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.