1.0 2010-04-08 22:08:08 UTC 2025-11-18 23:11:36 UTC FDB008548 Methyleugenol 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. 1-(3, 4-Dimethoxyphenyl)-2-propene 1, 2-Dimethoxy-4-(2-propenyl)benzene 1,2-Dimethoxy-4-(2-propenyl)benzene 4-Allyl-1, 2-dimethoxybenzene 4-Allyl-1,2-dimethoxy-benzene 4-Allyl-1,2-dimethyoxybenzene 4-Allylveratrole Allyl-1,2-dimethoxybenzene Benzene, 4-(2-propenyl)-1,2-dimethoxy Benzene, 4-allyl-1, 2-dimethoxy- Eugenol methyl Eugenol methyl ether FEMA 2475 Methyl eugenol Methyleugenol O-Methyleugenol C11H14O2 178.2277 178.099379692 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene methyl eugenol 93-15-2 COC1=C(OC)C=C(CC=C)C=C1 InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 ZYEMGPIYFIJGTP-UHFFFAOYSA-N 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. Dimethoxybenzenes Organic compounds Benzenoids Benzene and substituted derivatives Methoxybenzenes Aromatic homomonocyclic compounds Alkyl aryl ethers Anisoles Hydrocarbon derivatives Phenoxy compounds Alkyl aryl ether Anisole Aromatic homomonocyclic compound Dimethoxybenzene Ether Hydrocarbon derivative O-dimethoxybenzene Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound a small molecule phenylpropanoid Liquid logp 2.99 ALOGPS logs -2.98 ALOGPS solubility 1.88e-01 g/l ALOGPS melting_point Fp -4° logp 2.76 ChemAxon pka_strongest_basic -4.6 ChemAxon iupac 1,2-dimethoxy-4-(prop-2-en-1-yl)benzene ChemAxon average_mass 178.2277 ChemAxon mono_mass 178.099379692 ChemAxon smiles COC1=C(OC)C=C(CC=C)C=C1 ChemAxon formula C11H14O2 ChemAxon inchi InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3 ChemAxon inchikey ZYEMGPIYFIJGTP-UHFFFAOYSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 53.27 ChemAxon polarizability 19.89 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 4976 Specdb::MsIr 4977 Specdb::NmrOneD 3397 Specdb::EiMs 1247 Specdb::MsMs 61278 Specdb::MsMs 61279 Specdb::MsMs 61280 Specdb::MsMs 117780 Specdb::MsMs 117781 Specdb::MsMs 117782 Specdb::MsMs 374580 Specdb::MsMs 451199 Specdb::MsMs 2379162 Specdb::MsMs 2379163 Specdb::MsMs 2379164 Specdb::MsMs 2556363 Specdb::MsMs 2556364 Specdb::MsMs 2556365 Specdb::CMs 14812 Specdb::CMs 26879 Specdb::CMs 26880 Specdb::CMs 29096 Specdb::CMs 29543 Specdb::CMs 29544 Specdb::CMs 100975 Specdb::CMs 100976 Specdb::CMs 100977 Specdb::CMs 100978 Specdb::CMs 100979 Specdb::CMs 136336 Specdb::CMs 144070 HMDB31864 4918 #<Reference:0x000055ce30ce24b8> #<Reference:0x000055ce30ce21e8> Allspice Type 1 specific Pimenta dioica 375272 772.0 1525.0 19.0 mg/100 g Blackberry Type 1 specific Rubus Carrot Type 1 specific Daucus carota ssp. sativus 79200 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 Citrus Unknown generic Cloves Type 1 specific Syzygium aromaticum 219868 32.5 32.5 32.5 mg/100 g Evergreen blackberry Type 1 specific Rubus laciniatus Fruits Unknown generic Herbs and Spices Unknown generic Hyssop Type 1 specific Hyssopus officinalis 39324 5.35 5.35 5.35 mg/100 g Lemon balm Type 1 specific Melissa officinalis 39338 Mung bean Type 1 specific Vigna radiata 157791 Muskmelon Type 1 specific Cucumis melo 3656 Nutmeg Type 1 specific Myristica fragrans 51089 46.0 46.0 46.0 mg/100 g Pepper (Spice) Type 1 specific Piper nigrum 13216 Pomes Unknown generic Pot marjoram Type 1 specific Origanum onites 452416 0.0 0.0 0.0 mg/100 g Rocket salad (ssp.) Type 1 specific Eruca vesicaria ssp. sativa 29727 Rosemary Type 1 specific Rosmarinus officinalis 39367 0.6 0.6 0.6 mg/100 g Sour cherry Type 1 specific Prunus cerasus 140311 Soy bean Type 1 specific Glycine max 3847 Sweet basil Type 1 specific Ocimum basilicum 39350 125.65 125.65 125.65 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 141.05 141.05 141.05 mg/100 g Tarragon Type 1 specific Artemisia dracunculus 72341 159.5 159.5 159.5 mg/100 g White mustard Type 1 specific Sinapis alba 3728 Wild carrot Type 1 specific Daucus carota 4039 Winter savory Type 1 specific Satureja montana 49988 22.0 22.0 22.0 mg/100 g anise apricot balsam banana carnation chocolate cinnamon clove coconut creamy fresh mesquite musty oily peach plum raspberry spice spicy sweet vanilla warm Anesthetic 62 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti convulsant 204 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti feedant 275 Anti radicular 572 Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-oxidant 502 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. Antidote 236 Any protective agent counteracting or neutralizing the action of poisons. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Carcinogenic 762 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. Central nervous system depressant 812 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. DNA-binder 886 Fungicide 940 A substance used to destroy fungal pests. Fungistat 942 Hypothermic 1023 Insectifuge 1041 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Myorelaxant 1134 Name 936 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. Narcotic 1139 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. Nematicide 1141 A substance used to destroy pests of the phylum Nematoda (roundworms). Perfumery 1206 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Sedative 1311 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.