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
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-Allylanisole	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 chavicol	HMDB
Methyl chavicole	HMDB
Methyl chavicole (estragole)	HMDB
Methyl-chavicol	HMDB
O-Methyl-chavicol	HMDB
p-Allyl-anisole	HMDB
p-Allylanisole	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
Ether, P-allylphenyl methyl	HMDB
P-Allyl-anisole	HMDB

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 - 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	Spectrum
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-24fa3ff739ff064312ab	Spectrum
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-8900000000-5b42adf83e422cffefb6	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

MS/MS

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

NMR

Type	Description		View
1D NMR	1H NMR Spectrum		Spectrum
1D NMR	13C NMR Spectrum		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			DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
carcinogenic	50903	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-binder			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hepatocarcinogenic	50903	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
hypothermic			DUKE
insecticide	24852	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
insectifuge	24852	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
mutagenic			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	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.