Showing Compound Methylisoeugenol (FDB021536)

Record Information

Version

1.0

Creation date

2010-04-08 22:15:46 UTC

Update date

2019-11-26 03:20:31 UTC

Primary ID

FDB021536

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Methylisoeugenol

Description

Methylisoeugenol 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. Methylisoeugenol is a mild, bitter, and clove tasting compound. Methylisoeugenol is found, on average, in the highest concentration within a few different foods, such as nutmegs (Myristica fragrans), star anises (Illicium verum), and gingers (Zingiber officinale). Methylisoeugenol has also been detected, but not quantified in, several different foods, such as wild carrots (Daucus carota), carrots (Daucus carota ssp. sativus), sweet basils (Ocimum basilicum), tarragons (Artemisia dracunculus), and evergreen blackberries (Rubus laciniatus). This could make methylisoeugenol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methylisoeugenol.

CAS Number

6379-72-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(Z)-Methyl isoeugenol	ChEBI
cis-4-Propenyl veratrole	ChEBI
cis-Methyl isoeugenol	ChEBI
(e)-Methyl eugenol	HMDB
(e)-Methyl isoeugenol	HMDB
1,2-Dimethoxy-4-(1-propenyl)benzene, 9ci	HMDB
1,2-Dimethoxy-4-propenyl-(e)-benzene	HMDB
1,2-Dimethoxy-4-propenyl-benzene	HMDB
1,2-Dimethoxy-4-propenylbenzene	HMDB
1,3,4-Isoeugenol methyl ether	HMDB
1-(3,4-Dimethoxyphenyl)-1-propene	HMDB
1-Veratryl-1-propene	HMDB
3,4-Dimethoxypropenylbenzene	HMDB
4-(1-Propenyl)veratrole	HMDB
4-Propenyl-1,2-dimethoxybenzene	HMDB
4-Propenylveratrole	HMDB
4-trans-Propenylveratrole	HMDB
FEMA 2476	HMDB
Isoeugenol methyl ether	HMDB
Isoeugenyl methyl ether	HMDB
Isohomogenol	HMDB
Isomethyleugenol	HMDB, MeSH
Methyl isoeugenol	HMDB, MeSH
O-Methylisoeugenol	HMDB
trans-4-Propenylveratrole	HMDB
trans-Isomethyleugenol	HMDB, MeSH
trans-Methyl isoeugenol	HMDB
1,2-Dimethoxy-4-(1-e-propenyl)benzene	MeSH, HMDB
1,2-Dimethoxy-4-(1-propenyl)benzene	MeSH, HMDB
1,2-Dimethoxy-4-(1-Z-propenyl)benzene	MeSH, HMDB
Isomethyleugenol, (e)-isomer	MeSH, HMDB
Isomethyleugenol, (Z)-isomer	MeSH, HMDB
Methylisoeugenol	MeSH
(e)-methyl eugenol	biospider
(e)-methyl isoeugenol	biospider
1,2-Dimethoxy-4-(1-propenyl)benzene, 9CI	db_source
Benzene, 1,2-dimethoxy-4-propenyl-	biospider
Benzene, 1,2-dimethoxy-4-propenyl-, (E)-	biospider
O-methylisoeugenol	biospider
Trans-isomethyleugenol	biospider
Trans-methyl isoeugenol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	3.47	ALOGPS
logP	2.78	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	3	ChemAxon
Refractivity	54.34 m³·mol⁻¹	ChemAxon
Polarizability	19.92 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-[(1Z)-prop-1-en-1-yl]benzene

InChI Identifier

InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4-8H,1-3H3/b5-4-

InChI Key

NNWHUJCUHAELCL-PLNGDYQASA-N

Isomeric SMILES

COC1=C(OC)C=C(\C=C/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
Styrene
Phenol ether
Anisole
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

isomethyleugenol (CHEBI:50550 )

Ontology

No ontology term

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	Mp 16-17°	DFC
Boiling Point	Bp12 138-140°	DFC
Experimental Water Solubility	Not Available
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	n20D 1.5616	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(Z)-Methyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03fs-1900000000-3d41a0d29a7363963fbb	Spectrum
Predicted GC-MS	(Z)-Methyl isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-1b4a5c893c8cb3d52797	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-dd43f9e1c8e86b7ba6ff	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9500000000-20fd1ba2b53cc59be2ea	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-13d0af68ffab1cb5c56d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-02afbb666cbaaa0c075e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-07cr-4900000000-6a705aba56bdf50c3728	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-cde372377d8e900ad3a3	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fb9-0900000000-28cc89aae8d7b76189de	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9400000000-219c0ddce8933e6a09c3	2021-09-22	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-0900000000-75e41d1bbbb423dac95f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02u9-9800000000-aa3ed6a53e37b0107f0e	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

6877

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB41553

CRC / DFC (Dictionary of Food Compounds) ID

MVN84-F:NZP08-I

EAFUS ID

1891

Dr. Duke ID

METHYL-ISOEUGENOL|(E)-METHYL-ISOEUGENOL|ISOEUGENOL-METHYL-ETHER|TRANS-METHYL-ISOEUGENOL

BIGG ID

Not Available

KNApSAcK ID

C00002760

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1435071

SuperScent ID

Not Available

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-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
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 histaminic	37956	An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.	DUKE
Anti-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	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
Candidicide		An agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.	DUKE
Expectorant	52217	An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.	DUKE
Name	48318	flavor	DUKE
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Insect attractant	24852	A substance that lures insects, playing a biological role in pollination and mating. Therapeutically, it has applications in pest control and management. Key medical uses include monitoring and controlling insect-borne diseases, such as malaria and Zika virus, by attracting and trapping disease-carrying insects.	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
Toxic	52209	A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mild	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.
clove	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755