U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H14O2
Molecular Weight 178.2277
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYL EUGENOL

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C11H14O2
Molecular Weight 178.2277
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis.
1999 Aug 19
14-Week toxicity and cell proliferation of methyleugenol administered by gavage to F344 rats and B6C3F1 mice.
2001 Apr
Methyleugenol and eugenol variation in Ocimum basilicum cv. Genovese gigante grown in greenhouse and in vitro.
2001 Apr-Jun
Methyleugenol in Ocimum basilicum L. Cv. genovese gigante.
2001 Jan
Allomonal and hepatotoxic effects following methyl eugenol consumption in Bactrocera papayae male against Gekko monarchus.
2001 May
Identification of mammary carcinogens in rodent bioassays.
2002
Anticonvulsant activity of the leaf essential oil of Laurus nobilis against pentylenetetrazole- and maximal electroshock-induced seizures.
2002 Apr
Authenticity assessment of estragole and methyl eugenol by on-line gas chromatography-isotope ratio mass spectrometry.
2002 Feb 27
Floral synomone of a wild orchid, Bulbophyllum cheiri, lures Bactrocera fruit flies for pollination.
2002 Jun
Antifungal constituents of the essential oil fraction of Artemisia dracunculus L. Var. dracunculus.
2002 Nov 20
Anticonflict effects of rose oil and identification of its active constituents.
2002 Nov 22
Evidence for positive selection on the floral scent gene isoeugenol-O-methyltransferase.
2003 Feb
Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).
2003 Feb 12
Phylogenetic relationships among Bactrocera species (Diptera: Tephritidae) inferred from mitochondrial DNA sequences.
2003 Jan
Antifungal constituents of Melicope borbonica.
2004 Jul
Correlation of tumors with DNA adducts from methyl eugenol and tamoxifen in rats.
2004 May
Male sex pheromonal components derived from methyl eugenol in the hemolymph of the fruit fly Bactrocera papayae.
2004 Nov
Anticonvulsant activity and chemical composition of Artemisia dracunculus L. essential oil.
2004 Oct
Essential oil yield and quality of methyl eugenol rich Ocimum tenuiflorum L.f. (syn. O. sanctum L.) grown in south India as influenced by method of harvest.
2004 Oct 29
Evidence of natural hybridization between two sympatric sibling species of Bactrocera dorsalis complex based on pheromone analysis.
2005 Apr
The melon fruit fly, Bactrocera cucurbitae: a review of its biology and management.
2005 Dec 6
Molecular mechanisms of toxicity of important food-borne phytotoxins.
2005 Feb
Evaluation of in vitro antimicrobial activity of Thai basil oils and their micro-emulsion formulas against Propionibacterium acnes.
2006 Apr
Transport of methyl eugenol-derived sex pheromonal components in the male fruit fly, Bactrocera dorsalis.
2006 Aug
Women's health among the Chumash.
2006 Mar
[Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS].
2006 May
Use of biomonitoring data to evaluate methyl eugenol exposure.
2006 Nov
Polybrominated diphenyl ethers: a case study for using biomonitoring data to address risk assessment questions.
2006 Nov
Human cytochrome p450 enzyme specificity for the bioactivation of estragole and related alkenylbenzenes.
2007 May
Chemical composition and antimicrobial activity of volatile components from capitula and aerial parts of Rhaponticum acaule DC growing wild in Tunisia.
2008
New attractants for males of the solanaceous fruit fly Bactrocera latifrons.
2008 Dec
Screening of chemical composition, antimicrobial and antioxidant activities of Artemisia essential oils.
2008 May
Antifungal activity of essential oils of Croton species from the Brazilian Caatinga biome.
2008 May
Biological activity evaluation of the oils from Laurus nobilis of Tunisia and Algeria extracted by supercritical carbon dioxide.
2009
Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae.
2009 Feb
Bay leaves improve glucose and lipid profile of people with type 2 diabetes.
2009 Jan
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:19:38 GMT 2023
Edited
by admin
on Fri Dec 15 17:19:38 GMT 2023
Record UNII
29T9VA6R7M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYL EUGENOL
FCC   INCI  
INCI  
Official Name English
NSC-209528
Code English
4-ALLYL-1,2-DIMETHOXYBENZENE
Systematic Name English
CHAVIBETOL METHYL ETHER
Common Name English
1-ALLYL-3,4-DIMETHOXYBENZENE
Systematic Name English
BENZENE, 1,2-DIMETHOXY-4-(2-PROPENYL)-
Systematic Name English
METHYL EUGENOL [INCI]
Common Name English
METHYLEUGENOL
HSDB   MI  
Systematic Name English
METHYL EUGENOL [FCC]
Common Name English
ENT-21040
Code English
METHYLCHAVIBETOL
Common Name English
4-ALLYLVERATROLE
Systematic Name English
BENZENE, 1,2-DIMETHOXY-4-(2-PROPEN-1-YL)-
Systematic Name English
FEMA NO. 2475
Code English
METHYL EUGENOL ETHER
Common Name English
1,3,4-EUGENOL METHYL ETHER
Common Name English
NSC-8900
Code English
O-METHYLEUGENOL
Systematic Name English
VERATROLE, 4-ALLYL-
Systematic Name English
1-(3,4-DIMETHOXYPHENYL)-2-PROPENE
Systematic Name English
EUGENYL METHYL ETHER
FHFI  
Common Name English
METHYLEUGENOL [HSDB]
Common Name English
METHYL EUGENYL ETHER
Common Name English
1,2-DIMETHOXY-4-(2-PROPENYL)BENZENE
Systematic Name English
VERATROLE METHYL ETHER
Systematic Name English
BENZENE, 4-ALLYL-1,2-DIMETHOXY-
Systematic Name English
EUGENYL METHYL ETHER [FHFI]
Common Name English
METHYLEUGENOL [MI]
Common Name English
METHYLEUGENOL [IARC]
Common Name English
METHYLEUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 203900
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
NCI_THESAURUS C45175
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
JECFA EVALUATION EUGENYL METHYL ETHER
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
Code System Code Type Description
WIKIPEDIA
METHYL EUGENOL
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
CHEBI
4918
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
NCI_THESAURUS
C44401
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
SMS_ID
100000170586
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
RXCUI
1368373
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
202-223-0
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
MESH
C005223
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
FDA UNII
29T9VA6R7M
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
EVMPD
SUB184705
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
MERCK INDEX
m7414
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY Merck Index
HSDB
4504
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
JECFA MONOGRAPH
1768
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
CAS
93-15-2
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
DAILYMED
29T9VA6R7M
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
PUBCHEM
7127
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
NSC
8900
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
ALANWOOD
methyl eugenol
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
NSC
209528
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID5025607
Created by admin on Fri Dec 15 17:19:38 GMT 2023 , Edited by admin on Fri Dec 15 17:19:38 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
In view of the toxic properties documented for the oil and associated with beta-asarone , it has been recommended that only beta-asarone-free calamus root should be used in phytotherapy.
PARENT -> CONSTITUENT ALWAYS PRESENT