The invention belongs to the field of organic synthesis and particularly relates to a eugenol synthesis method. Methyl eugenol 4allyl1,2dimethoxybenzenecarboxylate and cuelure 4pacetoxyphenyl2butanone are highly attractive kairomone lures to oriental fruit fly, bactrocera dorsalis hendel, and melon fly, b. Methyl eugenol 1,2dimethoxy42propenylbenzene cas no. Methyleugenol is used in commercial products as a flavorant at concentrations of 5 to 52 ppm and in fragrances at concentrations of 0. Attraction of female and male bactrocera papayae to conspecific. Methyl eugenol was genotoxic in a range of in vivo and in vitro assays, although it was not mutagenic in bacterial cells. Following administration of a single oral dose of methyleugenol. Safe drinking water and toxic enforcement act of 1986. Screening assessment for the challenge benzene, 1,2.
Taking into account a dermal penetration factor of 40%. Methyl eugenol, food and flavor ingredient, fema no 2475. Methyl isoeugenol isomethyleugenol is a phenylpropanoid, the methyl ether of isoeugenol. Methyl eugenol is used as a fragrance in perfumes 0. Methyl eugenol me 4allyl1, 2dimethoxybenzene carboxylate is a widely distributed. Vibrational spectroscopic results are discussed in relation to computed structures and spectra of the low energy conformations of these molecules obtained from dft calculations at the b3lypccpvtz level. Methyl eugenol effects on bactrocera dorsalis male total. Methyl eugenol me 4allyl1, 2dimethoxybenzenecarboxylate is a widely distributed natural plant product and occurs in 200 plant species in 32 families found mainly in the tropics tan and nishida, 1996. Infrared and raman spectroscopy of eugenol, isoeugenol. If present in sufficiently high concentration, it will immediately deter the herbivore from further feeding on the affected part see section 3. It is consumed by humans and animals in many plants and fruits e.
Chemical listed effective november 16, 2001 as known to the state of california to cause cancer. The insect attractant methyl eugenol and the insecticide malathion are exempt from the requirement of tolerances on all raw agricultural commodities when used in combination in oriental fruit fly eradication programs under the authority of the u. The tendency of male bactrocera dorsalis hendel to revisit a methyl eugenol source following initial exposure was examined. It is one of the main components found in the essential oil extracted from acorus calamus, bark of croton malambo and rhizomes of zingiber zerumbet, hedychium coronarium and. Pdf different methods of methyl eugenol application enhance the. 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. Based on the lower end of the noel and applying a times safety factor for systemic effects a daily dose for methyl eugenol of 60.
Methyl eugenol is one of the main constituents of the essential oil of ocimum species. Methyl eugenol is produced by the methylation of eugenol 8. Its occurrence, distribution, and role in nature, especially in relation to insect behavior. Please see the following for information about the library and its accompanying search program. It is most effectively used in control release dispensers such as the ft mee wafer. Characterization of eugenolisoeugenol synthase and omethyltransferase. The agency has evaluated the potential risks associated with methyl eugenol and has determined, that there is a reasonable certainty that no harm to any population subgroup will result from dietary and water exposure to methyl eugenol from uses specified in the existing exemption for the requirement for tolerance for methyl eugenol under 40 cfr. Ir and raman spectra of eugenol, isoeugenol and methyl eugenol have been obtained in the liquid phase. It is also an attractant for the oriental fruit flies. Methyl eugenol as an attractant for oriental fruit fly, journal of economic entomology, volume 45.
The substance identity section is calculated from substance identification information from all echa databases. Essential oils chemical constituents of leaves of o. It is the methyl ether of eugenol and is important to insect behavior and pollination. Methyl eugenol is a component of several essential oils that are sold for use in aromatherapy, massage oils and alternative medicines 7. Methyl eugenol allylveratrol is a natural chemical compound classified as a phenylpropene, a type of phenylpropanoid. Prepared by the office of environmental health hazard assessment, calepa. Comparisonofmeandcldispenserswithfipronil and other. Methyl eugenol, as a constituent in leaves, fruits, stems, andor roots, may be released when that corresponding part of a plant is damaged as a result of feeding by an herbivore. Detecting traces of methyl eugenol in essential oils. The environmental monitoring of methyl eugenol, naled and. Health questions and answers for methyl eugenol in insect.
Use of biomonitoring data to evaluate methyl eugenol exposure. Chemical structures of methyl eugenol me and its analogs. In addition, methyl eugenol caused gene mutation in the liver of transgenic animals and induced mutation of. Methyl eugenol and cuelure traps for suppression of male. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, basil and bay leaf. Biosynthesis of methyleugenol and methylisoeugenol in daucus carota leaves. A mixture of 10% cuelure and 90% methyl eugenol showed the highest attractant activity and remained effective for 225 days in field tests. E b weathering trials of amulet cuelure and amulet methyl. Health questions and answers for methyleugenol in insect bait traps this material is not applied to fruit trees or food crops. According to the eugenol synthesis method, guaiacol and allyl chloride are used as raw materials and are subjected to a catalytic reaction through a catalyst thld to generate eugenol. Plastic bucket traps were evaluated as dispensers for methyl eugenol and cuelure for suppression of the 2 fruit flies in.
Biopesticides fact sheet for methyl eugenol me keywords. All mass spectra in this site plus many more are available from the nistepanih mass spectral library. Methyl eugenol is a naturally occurring flavour and fragrance found in a variety of different food sources, including spices, herbs and fruit and also as a component of natural essential oils. Packaging 1 kg in poly bottle 10, 25 kg in poly drum biochemphysiol actions taste at 1. Exposing males to me or protein is a promising post. Insects to methyl eugenol bucket traps with different preservative. Methyl eugenol mixed in different ratios with cuelure is used as an attractant for melon fly cadus cucurbitae coquillett. Eugenol and methyl eugenol chemotypes of essential oil of. Methyl eugenol bound to liver dna and formed dna adducts in vi vo and in vitro. Ft methyl eugenol is the male attractant for many species of bactrocera fruit fly including the oriental fruit fly and the carambola fruit fly. Pdf biosynthesis of methyleugenol and methylisoeugenol.
Global methyl eugenol market is estimated to reach xxx million usd in 2020 and projected to grow at the cagr of xx% during 20202025. Chemical structure of methyleugenol 4allyl1,2dimethoxybenzene. The role of me in citronella grass, cymbopogon nardus poaceae, in the strong attraction of dacus currently bactrocera fruit flies which also visited other plant species including flowers of papaya and colocasia antiquorum, was first discovered almost a century ago howlett 1915. Methyl eugenol as an attractant for oriental fruit fly journal of. Sixty years later, me was found to be the most active.
Tephritidae are strongly attracted to methyl eugenol me 1,2dimethoxy42propenylbenzene, a phenylpropanoid compound occurring in many plant. Methyl eugenol, a fruitfly attractant, from the browning leaves of proiphys amboinensis amaryllidaceae. Methyl eugenol me and inclusion of protein into the adult diet increase the mating competitiveness of the oriental fruit fly, bactrocera dorsalis hendel. Biopesticides fact sheet for methyl eugenol me author. Tephritidae are strongly attracted to methyl eugenol me 1,2dimethoxy42propenylbenzene. Department of agriculture, in accordance with the following directions and specifications. A total of 33 and 37 compounds were identified in the essential oil of. Anthraquinone, azt, bromate ion and its water soluble salts, bromoethane, diuron, fumonisn b1, isoxaflutole, methyl eugenol, gemfibrozil, and zileuton under consideration for listing. Methyl isoeugenol isomethyleugenol is a phenylpropanoid, the methyl ether of isoeugenol, found in certain essential oils. Covid19 impact on methyl eugenol market development. Estragole, safrole, methyl eugenol, trans anethole, myristicin, and elemicin are used as.
All these compounds typically enter the diet via a variety of different food sources, including spices. California epa california environmental protection agency. Kinetics data in rats are consistent with a rapid clearance from the blood, metabolism in the liver mediated by the p450 system, and excretion in the urine. Its occurrence, distribution, and role in nature, especially in. Please see the following for information about the. Synthesis of methyl eugenol from crude cloves leaf oil. It is present in concentrations of 8090% in clove bud oil and at 8288% in clove leaf oil.
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