Methyl eugenol

Last updated
Methyl eugenol
Methyleugenol.svg
Methyl-eugenol-3D-balls.png
Names
Preferred IUPAC name
1,2-Dimethoxy-4-(prop-2-enyl)benzene [1]
Other names
4-Allyl-1,2-dimethoxybenzene
Allylveratrol
4-Allylveratrol
Eugenol methyl ether
Methyleugenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.022 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-223-0
KEGG
PubChem CID
UNII
  • InChI=1S/C11H14O2/c1-4-5-9-6-7-10(12-2)11(8-9)13-3/h4,6-8H,1,5H2,2-3H3
  • COc1cc(ccc1OC)CC=C
Properties
C11H14O2
Molar mass 178.231 g·mol−1
Density 0.98 g/cm3
Melting point -2 °C
Boiling point 254.7 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [2] 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. [3]

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. [4] 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. [5]

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) [6] [ citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Flavoring</span> Food additive used to change its aroma or taste

A flavoring, also known as flavor or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustatory and olfactory systems. Along with additives, other components like sugars determine the taste of food.

<span class="mw-page-title-main">Pollinator</span> Animal that moves pollen from the male anther of a flower to the female stigma

A pollinator is an animal that moves pollen from the male anther of a flower to the female stigma of a flower. This helps to bring about fertilization of the ovules in the flower by the male gametes from the pollen grains.

<span class="mw-page-title-main">Food coloring</span> Substance used to color to food or drink

Food coloring, or color additive, is any dye, pigment, or substance that imparts color when it is added to food or drink. They come in many forms consisting of liquids, powders, gels, and pastes. Food coloring is used in both commercial food production and domestic cooking. Food colorants are also used in a variety of non-food applications, including cosmetics, pharmaceuticals, home craft projects, and medical devices.

<i>Bulbophyllum</i> Genus of orchids

Bulbophyllum is a genus of mostly epiphytic and lithophytic orchids in the family Orchidaceae. It is the largest genus in the orchid family and one of the largest genera of flowering plants with more than 2,000 species, exceeded in number only by Astragalus. These orchids are found in diverse habitats throughout most of the warmer parts of the world including Africa, southern Asia, Latin America, the West Indies, and various islands in the Indian and Pacific Oceans. Orchids in this genus have thread-like or fibrous roots that creep over the surface of trees or rocks or hang from branches. The stem is divided into a rhizome and a pseudobulb, a feature that distinguished this genus from Dendrobium. There is usually only a single leaf at the top of the pseudobulb and from one to many flowers are arranged along an unbranched flowering stem that arises from the base of the pseudobulb. Several attempts have been made to separate Bulbophyllum into smaller genera, but most have not been accepted by the World Checklist of Selected Plant Families.

<span class="mw-page-title-main">Ethyl carbamate</span> Chemical compound

Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely used, but naturally forms in low quantities in many types of fermented foods and drinks.

<span class="mw-page-title-main">Euglossini</span> Tribe of bees

The tribe Euglossini, in the subfamily Apinae, commonly known as orchid bees or euglossine bees, are the only group of corbiculate bees whose non-parasitic members do not all possess eusocial behavior.

<span class="mw-page-title-main">Insect trap</span> Device used to monitor or reduce insect populations

Insect traps are used to monitor or directly reduce populations of insects or other arthropods, by trapping individuals and killing them. They typically use food, visual lures, chemical attractants and pheromones as bait and are installed so that they do not injure other animals or humans or result in residues in foods or feeds. Visual lures use light, bright colors and shapes to attract pests. Chemical attractants or pheromones may attract only a specific sex. Insect traps are sometimes used in pest management programs instead of pesticides but are more often used to look at seasonal and distributional patterns of pest occurrence. This information may then be used in other pest management approaches.

<span class="mw-page-title-main">Azodicarbonamide</span> Chemical compound

Azodicarbonamide, ADCA, ADA, or azo(bis)formamide, is a chemical compound with the molecular formula C2H4O2N4. It is a yellow to orange-red, odorless, crystalline powder. It is sometimes called a 'yoga mat' chemical because of its widespread use in foamed plastics. It was first described by John Bryden in 1959.

<span class="mw-page-title-main">Zingerone</span> Chemical compound

Zingerone, also called vanillylacetone, is a major flavor component of ginger, providing the sweet flavor of cooked ginger. Zingerone is a crystalline solid that is sparingly soluble in water and soluble in ether.

A semiochemical, from the Greek σημεῖον (semeion), meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication can be divided into two broad classes: communication between individuals of the same species (intraspecific) or communication between different species (interspecific).

<span class="mw-page-title-main">Brown FK</span> Chemical compound

Brown FK, also called Kipper Brown, Chocolate Brown FK, and C.I. Food Brown 1, is a brown mixture of six synthetic azo dyes, with addition of sodium chloride, and/or sodium sulfate. It is very soluble in water. When used as a food dye, its E number is E154.

<i>Bactrocera dorsalis</i> Species of insect

Bactrocera dorsalis, previously known as Dacus dorsalis and commonly referred to as the oriental fruit fly, is a species of tephritid fruit fly that is endemic to Southeast Asia. It is one of the major pest species in the genus Bactrocera with a broad host range of cultivated and wild fruits. Male B. dorsalis respond strongly to methyl eugenol, which is used to monitor and estimate populations, as well as to annihilate males as a form of pest control. They are also important pollinators and visitors of wild orchids, Bulbophyllum cheiri and Bulbophyllum vinaceum in Southeast Asia, which lure the flies using methyl eugenol.

<span class="mw-page-title-main">Bees and toxic chemicals</span>

Bees can suffer serious effects from toxic chemicals in their environments. These include various synthetic chemicals, particularly insecticides, as well as a variety of naturally occurring chemicals from plants, such as ethanol resulting from the fermentation of organic materials. Bee intoxication can result from exposure to ethanol from fermented nectar, ripe fruits, and manmade and natural chemicals in the environment.

<span class="mw-page-title-main">Raspberry ketone</span> Chemical compound

Raspberry ketone is a natural phenolic compound that is the primary aroma compound of red raspberries.

<i>Bactrocera cucurbitae</i> Species of fly

Bactrocera cucurbitae, the melon fly, is a fruit fly of the family Tephritidae. It is a serious agricultural pest, particularly in Hawaii.

<i>Bulbophyllum baileyi</i> Species of orchid from Australia and New Guinea

Bulbophyllum baileyi, commonly known as the fruit fly orchid, is a species of epiphytic or lithophytic orchid that is native to Queensland and New Guinea. It has coarse, creeping rhizomes, curved, yellowish pseudobulbs with a single thick, fleshy leaf, and a single cream-coloured flower with yellow, red or purple spots. It grows on trees and rocks in open forest, often in exposed places.

<i>Bactrocera invadens</i> Species of fly

Bactrocera (Bactrocera) invadens is the name given to tephritid fruit flies that were introduced to East Africa from Sri Lanka and subsequently invaded practically the whole of Sub-Saharan Africa, hence the species name "invadens". It was first shown to be the same biological species as B. dorsalis s.s. by possessing identical sex pheromonal components after consumption of methyl eugenol, and also based on CO1 and rDNA sequences. Subsequently, it was agreed that B. invadens, B. papayae and B. philippinensis be synonymized as B. dorsalis. To counteract its detrimental effects to the fruit business, the industry resorts to cold treatment in order to get rid of the larvae.

The Food Chemicals Codex (FCC) is a collection of internationally recognized standards for the purity and identity of food ingredients.

An attractant is any chemical that attracts an organism, e.g. i) synthetic lures; ii) aggregation and sex pheromones ; and iii) synomone

<span class="mw-page-title-main">Pollination of orchids</span>

The pollination of orchids is a complex chapter in the biology of this family of plants that are distinguished by the complexity of their flowers and by intricate ecological interactions with their pollinator agents. It has captured the attention of numerous scientists over time, including Charles Darwin, father of the theory of evolution by natural selection. Darwin published in 1862 the first observations of the fundamental role of insects in orchid pollination, in his book The Fertilization of Orchids. Darwin stated that the varied stratagems orchids use to attract their pollinators transcend the imagination of any human being.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/7127#section=Names-and-Identifiers
  2. Tan, Keng Hong; Nishida, Ritsuo (2012). "Methyl Eugenol: Its Occurrence, Distribution, and Role in Nature, Especially in Relation to Insect Behavior and Pollination". Journal of Insect Science. 12 (56): 1–60. doi:10.1673/031.012.5601. PMC   3500151 . PMID   22963669.
  3. Tan, Keng Hong; Nishida, Ritsuo (2012). "Methyl Eugenol: Its Occurrence, Distribution, and Role in Nature, Especially in Relation to Insect Behavior and Pollination". Journal of Insect Science. 12 (56): 1–60. doi:10.1673/031.012.5601. PMC   3500151 . PMID   22963669.
  4. Aubrey, Allison (6 October 2018). "FDA Bans Use of 7 Synthetic Food Additives After Environmental Groups Sue". NPR. Retrieved 14 June 2021.
  5. 83 FR 50490
  6. Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006