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

Synonym	Source
1,2-Dimethoxy-4-(2-propenyl)benzene	ChEBI
Eugenol methyl ether	ChEBI
Methyl eugenol	ChEBI
O-Methyleugenol	Kegg
Methyleugenol	ChEBI
1, 2-Dimethoxy-4-(2-propenyl)benzene	HMDB
1-(3, 4-Dimethoxyphenyl)-2-propene	HMDB
4-Allyl-1, 2-dimethoxybenzene	HMDB
4-Allyl-1,2-dimethoxy-benzene	HMDB
4-Allyl-1,2-dimethyoxybenzene	HMDB
4-Allylveratrole	HMDB
Allyl-1,2-dimethoxybenzene	HMDB
Benzene, 4-(2-propenyl)-1,2-dimethoxy	HMDB
Eugenol methyl	HMDB
FEMA 2475	HMDB
4-Allyl-1,2-dimethoxybenzene	MeSH
1-Allyl-3,4-dimethoxybenzene	MeSH
1,2-Dimethoxy-4-(2-propen-1-yl)benzene	PhytoBank
1,2-Dimethoxy-4-allylbenzene	PhytoBank
1,3,4-Eugenol methyl ether	PhytoBank
1-(3,4-Dimethoxyphenyl)-2-propene	PhytoBank
3,4-Dimethoxy-1-(2-propenyl)benzene	PhytoBank
3,4-Dimethoxyallylbenzene	PhytoBank
3-(3,4-Dimethoxyphenyl)-1-propene	PhytoBank
3-(3,4-Dimethoxyphenyl)propene	PhytoBank
Chavibetol methyl ether	PhytoBank
Eugenyl methyl ether	PhytoBank
Methyl eugenol ether	PhytoBank
Methyl eugenyl ether	PhytoBank
Methylchavibetol	PhytoBank
Veratrole methyl ether	PhytoBank
Benzene, 4-allyl-1, 2-dimethoxy-	biospider

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

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 74.13%; H 7.92%; O 17.95%	DFC
Melting Point	Fp -4°	DFC
Boiling Point	Bp12 125-127°	DFC
Experimental Water Solubility	0.5 mg/mL at 25 oC	CHEMICALS INSPECTION AND TESTING INSTITU (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	Not Available
Refractive Index	Not Available

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anesthetic		A drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti convulsant	52217	An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.	DUKE
Antidote	50247	An agent that counteracts a poison or toxin, neutralizing its harmful effects. It plays a biological role in reversing toxicity, and has therapeutic applications in treating poisoning, overdose, and envenomation. Key medical uses include emergency treatment for snake bites, drug overdose, and chemical exposure.	DUKE
Anti feedant		A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	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
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	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
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Fungistat		An agent that inhibits fungal growth, used to prevent fungal infections, commonly applied in therapeutic applications such as treating skin and nail infections, and managing fungal diseases in immunocompromised patients.	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
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
Myorelaxant		An agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.	DUKE
Narcotic	35482	A pain-relieving agent that binds to opioid receptors, reducing pain perception. Therapeutically, narcotics are used to manage moderate to severe pain, cough, and diarrhea. Key medical uses include treating acute and chronic pain, cough suppression, and relieving diarrhea and dyspnea in terminally ill patients.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	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
Sedative	35717	An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
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.
spice	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
creamy	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
oily	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
anise	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
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.
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
mesquite	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
musty	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
banana	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
coconut	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
peach	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
plum	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
raspberry	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
fresh	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
carnation	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.