Showing Compound Methyleugenol (FDB008548)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:08 UTC

Update date

2020-09-17 15:31:40 UTC

Primary ID

FDB008548

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methyleugenol

Description

Methyleugenol, also known as 4-allylveratrole, belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying two methoxy groups. Methyleugenol is a sweet, anise, and apricot tasting compound. Outside of the human body, Methyleugenol is found in the highest concentration within a few different foods, such as allspices, tarragons, and sweet bay and in a lower concentration in sweet basils, rosemaries, and hyssops. Methyleugenol has also been detected, but not quantified, in several different foods, such as soybeans, evergreen blackberries, muskmelons, citrus, and pomes. As of October 2018, the US FDA withdrew authorization for the use of methyl eugenol as a synthetic flavoring substance for use in food because petitioners provided data demonstrating that these additives induce cancer in laboratory animals. FDA noted the action was despite its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use. Methyleugenol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Methyl eugenol is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. It is the methyl ether of eugenol and it is important in the plant-insect interaction and pollination. Their ability to attract insects, particularly Bactrocera fruit flies was first noticed in 1915 by F. M. Howlett. The compound may have evolved in response to pathogens, as methyl eugenol has some antifungal activity. Methyl eugenol has been identified in a number of plants (over 450 species from 80 families including both angiosperm and gymnosperm families) and has a role in attracting pollinators. About 350 plant species have them as a component of floral fragrance.

CAS Number

93-15-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1, 2-Dimethoxy-4-(2-propenyl)benzene	HMDB
1,2-Dimethoxy-4-(2-propen-1-yl)benzene	PhytoBank
1,2-Dimethoxy-4-(2-propenyl)benzene	ChEBI
1,2-Dimethoxy-4-allylbenzene	PhytoBank
1,3,4-Eugenol methyl ether	PhytoBank
1-(3, 4-Dimethoxyphenyl)-2-propene	HMDB
1-(3,4-Dimethoxyphenyl)-2-propene	PhytoBank
1-Allyl-3,4-dimethoxybenzene	MeSH
3,4-Dimethoxy-1-(2-propenyl)benzene	PhytoBank
3,4-Dimethoxyallylbenzene	PhytoBank

Showing 1 to 10 of 32 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.19 g/L	ALOGPS
logP	2.99	ALOGPS
logP	2.76	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.27 m³·mol⁻¹	ChemAxon
Polarizability	19.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H14O2

IUPAC name

1,2-dimethoxy-4-(prop-2-en-1-yl)benzene

InChI Identifier

InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3

InChI Key

ZYEMGPIYFIJGTP-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

Classification

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Anisole
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylpropanoid (CHEBI:4918 )
a small molecule (CPD-6482 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Personal care product

Environmental:

Tobacco smoke

Biological:

Plant:

Cucurbitaceae

Role

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp12 125-127°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	0.5 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (1992)
Isoelectric point	Not Available
Mass Composition	C 74.13%; H 7.92%; O 17.95%	DFC
Melting Point	Fp -4°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-6a0a17f77c5384cea66f	2014-09-20	View Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-004i-6900000000-24e258249ebb81a10db8	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-001i-6900000000-7eab85ab8f89486d0c67	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-004i-6900000000-511a7254b57b1693d125	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-004i-6900000000-6e7986f7be4dcc512bf5	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-001l-6900000000-0b489e050538331d3090	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-004i-6900000000-24e258249ebb81a10db8	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-001i-6900000000-7eab85ab8f89486d0c67	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-004i-6900000000-511a7254b57b1693d125	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-004i-6900000000-6e7986f7be4dcc512bf5	Spectrum
GC-MS	Methyleugenol, non-derivatized, GC-MS Spectrum	splash10-001l-6900000000-0b489e050538331d3090	Spectrum
Predicted GC-MS	Methyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03g0-1900000000-ef346d457b34fcee14be	Spectrum
Predicted GC-MS	Methyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Methyleugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0006-0900000000-d41423501ff6a0caec1e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-006t-1910000000-c6bd5f4739dc2d3b4f99	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-5bcc530b76def442eca8	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1900000000-7363ea03a8cd36e7f50a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9600000000-8efff378856493d57d48	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-248b8d584ce0c311ffc0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8e61ac867ff1e4b6bdd8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-07cr-4900000000-e8817397f71772abc175	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-583273c8100f9e55b4bd	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-0900000000-2884ce971c57cbd816d5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02u9-9800000000-4811899c7b2ebb02f836	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-98bc20876c03ad8e0e92	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ufr-0900000000-ba7858c7a47bbfdf0ab3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9400000000-86967ab180df17622b53	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

21106140

ChEMBL ID

Not Available

KEGG Compound ID

C10454

Pubchem Compound ID

7127

Pubchem Substance ID

Not Available

ChEBI ID

4918

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB31864

CRC / DFC (Dictionary of Food Compounds) ID

HGZ80-F:DNB75-W

EAFUS ID

1331

Dr. Duke ID

3,4-DIMETHOXY-ALLYL-BENZENE|METHYL-EUGENOL|EUGENOL-METHYL-ETHER

BIGG ID

Not Available

KNApSAcK ID

C00002741

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

93-15-2

GoodScent ID

rw1008291

SuperScent ID

7127

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anesthetic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti feedant			DUKE
anti radicular			DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
antidote	50247	Any protective agent counteracting or neutralizing the action of poisons.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	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

Showing 1 to 10 of 23 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
anise	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
apricot	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
balsam	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
banana	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
carnation	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
chocolate	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
cinnamon	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.
clove	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 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.
coconut	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
creamy	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695