Compound: Methyl eugenol
SMILES: O(c1c(OC)ccc(c1)CC=C)C
InChIKey: ZYEMGPIYFIJGTP-UHFFFAOYSA-N
Synonyms: Methyl eugenol, METHYLEUGENOL, 93-15-2, 4-Allyl-1,2-dimethoxybenzene, Eugenol methyl ether, 4-Allylveratrole, O-Methyleugenol, Eugenyl methyl ether, Veratrole methyl ether, Methyl eugenol ether, 1-Allyl-3,4-dimethoxybenzene, 1,2-Dimethoxy-4-(2-propenyl)benzene, Benzene, 1,2-dimethoxy-4-(2-propenyl)-, Methyl eugenyl ether, 3,4-Dimethoxyallylbenzene, 1,2-dimethoxy-4-prop-2-enylbenzene, 1,3,4-Eugenol methyl ether, 1,2-Dimethoxy-4-allylbenzene, Benzene, 4-allyl-1,2-dimethoxy-, 1-(3,4-Dimethoxyphenyl)-2-propene, ENT 21040, FEMA No. 2475, FEMA Number 2475, 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene, 29T9VA6R7M, NSC-8900, ENT-21040, NSC-209528, VERATROLE, 4-ALLYL-, CHAVIBETOL METHYL ETHER, CHEBI:4918, NSC8900, NSC209528, RefChem:818610, 202-223-0, 3-(3,4-dimethoxyphenyl)-1-propene, 4-allyl-1,2-dimethoxy-benzene, MFCD00008652, Eugenol methyl, 1,2-Dimethoxy-4-(2-propen-1-yl)benzene, NSC 209528, 4-Allyl-1,2-dimethyoxybenzene, DTXSID5025607, 1,2-dimethoxy-4-(2-propenyl)-benzene, Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)-, Benzene, 4-(2-propenyl)-1,2-dimethoxy, 1,4-Eugenol methyl ether, O-Methyl eugenol, DTXCID505607, WLN: 1U2R CO1 DO1, Allylveratrol, Caswell No. 579AB, Benzene,2-dimethoxy-4-(2-propenyl)-, CAS-93-15-2, SMR000112378, CCRIS 746, HSDB 4504, o-Methyl eugenol ether, Eugenol EP Impurity E, EINECS 202-223-0, EPA Pesticide Chemical Code 203900, BRN 1910871, UNII-29T9VA6R7M, methyl-eugenol, AI3-21040, methyl ester eugenol, Eugenol-methyl ether, METHYLCHAVIBETOL, Methyl Eugenol (Standard), METHYLEUGENOL [MI], EC 202-223-0, Allyl-1,2-dimethoxybenzene, METHYLEUGENOL [HSDB], METHYLEUGENOL [IARC], METHYL EUGENOL [FCC], MLS001065600, MLS001333205, MLS001333206, SCHEMBL113794, CHEMBL108861, orb1303353, orb3140088, SCHEMBL2093906, SCHEMBL8905424, 1,2-Dimethoxy-4-allyl benzene, 4-Allyl-1, 2-dimethoxybenzene, SCHEMBL10108224, SCHEMBL29376951, FEMA 2475, HY-N6996R, Methyl eugenol, >=98%, FCC, GLXC-05254, HMS2269M09, HMS3886M22, Methyl eugenol, analytical standard, EUGENYL METHYL ETHER [FHFI], HY-N6996, MSK21044, Tox21_202347, Tox21_300071, BBL027720, BDBM50379791, EBC-47309, SBB007916, STK801819, 4-Allyl-1,2-dimethoxybenzene, 99%, AKOS015838877, 1-(3, 4-Dimethoxyphenyl)-2-propene, CS-W017325, Dimethoxy-4-(prop-2-en-1-yl)benzene, 1, 2-Dimethoxy-4-(2-propenyl)benzene, NCGC00091474-01, NCGC00091474-02, NCGC00091474-03, NCGC00091474-04, NCGC00254085-01, NCGC00259896-01, AC-34351, AS-14807, SY050658, DB-002806, D1360, NS00009255, S5755, ST50330558, E80630, EN300-698375, F022318, Q419829, Z1255398904, METHYLEUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC], Benzene, 1,2-dimethoxy-4-(2-propen-1-yl)-;Benzene, 4-allyl-1,2-dimethoxy-;FEMA No. 2475
Theoretical properties:
molecular_formula: C11H14O2
molecular_weight: 178.23 g/mol
exact_mass: 178.099379685 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 4
heavy_atom_count: 13
topological_polar_surface_area: 18.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from hexane
color: Crystals from hexane
odor: Mild-spicy, slightly herbal odor
boiling_point: 490.5 °F at 760 mmHg (NTP, 1992)
melting_point: 25 °F (NTP, 1992)
density: 1.0396 at 68 °F (NTP, 1992) - Denser than water; will sink
solubility: less than 1 mg/mL at 66 °F (NTP, 1992)
flash_point: 210 °F (NTP, 1992)
vapor_pressure: 0.02 mmHg at 68 °F ; 1 mmHg at 185.0 °F (NTP, 1992)
Descriptions:
pubchem: Methyleugenol can cause cancer according to The National Toxicology Program.
chembl: METHYLEUGENOL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Methyl eugenol (allylveratrol) is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid.  It is the methyl ether of eugenol and is important to insect behavior and pollination. It is found in various essential oils.
Methyl eugenol is found 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. Their ability to attract insects, particularly Bactrocera fruit flies (particularly, Bactrocera dorsalis male 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. It also repels many insects.
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 (including the Natural Resources Defense Council, the Center for Food Safety, and the Center for Science in the Public Interest) 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.
In European Union member states, starting in 2021, any product that contains more than 0.01% of Methyl Eugenol must contain a label to this effect this as per the CLP regulation (Regulation (EC) No 1272/2008)