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 Phenylpropene is the organic compound with the formula C6H5CH2CH=CH2. It is a colorless liquid. The compound consists of a phenyl group attached to allyl. Phenylpropene isomerizes to trans-propenylbenzene. In plant biochemistry, the phenylprop ...

, a type of

phenylpropanoid The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of ...

. It is the methyl

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

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, basil ...

and is important to insect behavior and

pollination Pollination is the transfer of pollen from an anther of a plant to the stigma of a plant, later enabling fertilisation and the production of seeds, most often by an animal or by wind. Pollinating agents can be animals such as insects, birds ...

. 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 o ...

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 (), commonly called angiosperms. The term "angiosperm" is derived from the Greek words ('container, vessel') and ('seed'), and refers to those plants th ...

and

gymnosperm The gymnosperms ( lit. revealed seeds) are a group of seed-producing plants that includes conifers, cycads, ''Ginkgo'', and gnetophytes, forming the clade Gymnospermae. The term ''gymnosperm'' comes from the composite word in el, γυμνό� ...

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 ''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 ''Bactro ...

'' 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 crypto ...

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, Chicago, Bo ...

, the

Center for Food Safety The Center for Food Safety (CFS) is a 501c3, U.S. non-profit advocacy organization, based in Washington, D.C. It maintains an office in San Francisco, California. The executive director is Andrew Kimbrell, an attorney. Its stated mission is to ...

, 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 that advocates for safer and healthier foods. History and funding CSPI is a consumer advocacy organization. Its f ...

) 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. From 2021 any product that contains more than 0.01% of Methyl Eugenol has to be stated as per the CLP regulation (Regulation (EC) No 1272/2008) https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX%3A32008R1272

References

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

See also

References