Methyl eugenol (allylveratrol) is a natural

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

classified as a phenylpropene, a type of

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and ...

. It is the methyl

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

eugenol Eugenol is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. It is a colorless to pale yellow, aromatic oily liquid extracted from certain essential oils especially from clove, nutmeg, cinnamon, ...

and is important to insect behavior and

pollination Pollination is the transfer of pollen from an anther of a plant to the stigma (botany), stigma of a plant, later enabling fertilisation and the production of seeds. Pollinating agents can be animals such as insects, for example bees, beetles or bu ...

. It is found in various

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

s. Methyl eugenol is found in a number of plants (over 450 species from 80 families including both

angiosperm Flowering plants are plants that bear flowers and fruits, and form the clade Angiospermae (). The term angiosperm is derived from the Greek words (; 'container, vessel') and (; 'seed'), meaning that the seeds are enclosed within a fruit ...

and

gymnosperm The gymnosperms ( ; ) are a group of woody, perennial Seed plant, seed-producing plants, typically lacking the protective outer covering which surrounds the seeds in flowering plants, that include Pinophyta, conifers, cycads, Ginkgo, and gnetoph ...

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 ''Bactrocera'' is a large genus of tephritid fruit flies, with close to 500 species currently described and accepted. Name The genus name is derived from Ancient Greek Ancient Greek (, ; ) includes the forms of the Greek language used ...

'' fruit flies (particularly, ''

Bactrocera dorsalis ''Bactrocera dorsalis'', previously known as ''Dacus dorsalis'' and commonly referred to as the oriental fruit fly, is a species of Tephritidae, tephritid fruit fly that is endemism, endemic to Southeast Asia. It is one of the major Pest (organis ...

'' 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 An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as ...

activity. It also repels many insects. As of October 2018, the US

FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

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 Natural Resources Defense Council (NRDC) is a United States–based 501(c)(3) non-profit international environmental advocacy group, with its headquarters in New York City and offices in Washington, D.C., San Francisco, Los Angeles, Chicag ...

, the Center for Food Safety, and the

Center for Science in the Public Interest The Center for Science in the Public Interest (CSPI) is a Washington, D.C.–based non-profit watchdog and consumer advocacy group. History and funding CSPI is a consumer advocacy organization. Its focus is nutrition and health, food safety ...

) 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 The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...

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 The CLP Regulation (for "Classification, Labelling and Packaging") is a European Union regulation from 2008, which aligns the European Union system of classification, labelling and packaging of chemical substances and mixtures to the Globally ...

( Regulation (EC) No 1272/2008)

References

{{Phenylpropene Phenylpropenes Allyl compounds IARC Group 2A carcinogens O-methylated natural phenols

See also

References