Anethole (also known as anise camphor) is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

that is widely used as a

flavoring A flavoring (or flavouring), also known as flavor (or flavour) 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 g ...

substance. It is a derivative of

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 phenylpro ...

, a type of aromatic compound that occurs widely in nature, in

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. It is in the class 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 ...

organic compounds. It contributes a large component of the odor and flavor of

anise Anise (; '), also called aniseed or rarely anix is a flowering plant in the family Apiaceae native to Eurasia. The flavor and aroma of its seeds have similarities with some other spices and herbs, such as star anise, fennel, licorice, and t ...

and

fennel Fennel (''Foeniculum vulgare'') is a flowering plant species in the carrot family. It is a hardy, perennial herb with yellow flowers and feathery leaves. It is indigenous to the shores of the Mediterranean but has become widely naturalized ...

(both in the botanical family

Apiaceae Apiaceae or Umbelliferae is a family of mostly aromatic flowering plants named after the type genus '' Apium'' and commonly known as the celery, carrot or parsley family, or simply as umbellifers. It is the 16th-largest family of flowering plan ...

), anise myrtle (

Myrtaceae Myrtaceae, the myrtle family, is a family of dicotyledonous plants placed within the order Myrtales. Myrtle, pōhutukawa, bay rum tree, clove, guava, acca (feijoa), allspice, and eucalyptus are some notable members of this group. All sp ...

liquorice Liquorice (British English) or licorice (American English) ( ; also ) is the common name of ''Glycyrrhiza glabra'', a flowering plant of the bean family Fabaceae, from the root of which a sweet, aromatic flavouring can be extracted. The liqu ...

(

Fabaceae The Fabaceae or Leguminosae,International Code of Nomenc ...

), magnolia blossoms, and

star anise ''Illicium verum'' is a medium-sized evergreen tree native to northeast Vietnam and southwest China. A spice commonly called star anise, staranise, star anise seed, star aniseed, star of anise, Chinese star anise, or badian that closely resemb ...

(

Schisandraceae Schisandraceae is a family of flowering plants with 3 known genera and a total of 92 known species. Such a family has been recognized by most taxonomists, at least for the past several decades. Before that, the plants concerned were assigned to f ...

). Closely related to anethole is its

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Is ...

estragole Estragole (''p''-allylanisole, methyl chavicol) is a phenylpropene, a natural organic compound. Its chemical structure consists of a benzene ring substituted with a methoxy group and an allyl group. It is an isomer of anethole, differing with res ...

, abundant in

tarragon Tarragon (''Artemisia dracunculus''), also known as estragon, is a species of perennial herb in the family Asteraceae. It is widespread in the wild across much of Eurasia and North America and is cultivated for culinary and medicinal purposes. ...

(

Asteraceae The family Asteraceae, alternatively Compositae, consists of over 32,000 known species of flowering plants in over 1,900 genera within the order Asterales. Commonly referred to as the aster, daisy, composite, or sunflower family, Compositae ...

) and

basil Basil (, ; ''Ocimum basilicum'' , also called great basil, is a culinary herb of the family Lamiaceae (mints). It is a tender plant, and is used in cuisines worldwide. In Western cuisine, the generic term "basil" refers to the variety also k ...

(

Lamiaceae The Lamiaceae ( ) or Labiatae are a family of flowering plants commonly known as the mint, deadnettle or sage family. Many of the plants are aromatic in all parts and include widely used culinary herbs like basil, mint, rosemary, sage, savory ...

), that has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as ...

but exhibits high solubility in

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...

. This trait causes certain anise-flavored

liqueur A liqueur (; ; ) is an alcoholic drink composed of spirits (often rectified spirit) and additional flavorings such as sugar, fruits, herbs, and spices. Often served with or after dessert, they are typically heavily sweetened and un-aged beyon ...

s to become opaque when diluted with water; the ouzo effect.

Structure and production

Anethole is an aromatic, unsaturated

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 ...

related to lignols. It exists as both ''cis''–''trans'' isomers (see also ''E''–''Z'' notation), involving the double bond outside the ring. The more abundant isomer, and the one preferred for use, is the ''

trans Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Arts, entertainment, and media * Trans (festival), a former festival in Belfast, Northern Ireland, United Kingdom * ''Trans'' (fil ...

'' or ''E'' isomer. Like related compounds, anethole is poorly soluble in water. Historically, this property was used to detect adulteration in samples. Most anethole is obtained from

turpentine Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthene, terebinthine and (colloquially) turps) is a fluid obtained by the distillation of resin harvested from living trees, mainly pines. Mainly used as a special ...

-like extracts from trees. Of only minor commercial significance, anethole can also be isolated from essential oils. Currently Banwari Chemicals Pvt Ltd situated in Bhiwadi, Rajasthan, India is the leading manufacuterer of Anethole. It is prepared commercially from 4-methoxy

propiophenone Propiophenone (shorthand: benzoylethane or BzEt) is an aryl ketone. It is a colorless, sweet-smelling liquid that is insoluble in water, but miscible with organic solvents. It is used in the preparation of other compounds. Production Propiophenon ...

, which is prepared from

anisole Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound i ...

Uses

Flavoring

Anethole is distinctly

sweet Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketone ...

, measuring 13 times sweeter than

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or do ...

. It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinks

ouzo Ouzo ( el, ούζο, ) is a dry anise-flavored aperitif that is widely consumed in Greece. It is made from rectified spirits that have undergone a process of distillation and flavoring. Its taste is similar to other anise liquors like pastis, ...

rakı Rakı or raki (, Turkish pronunciation: ) is an alcoholic drink made of twice-distilled grapes. It is the national drink of Turkey. It is also popular in other Balkan countries as an apéritif as well as in Kazakhstan. It is often served with ...

anisette Anisette, or Anis, is an anise-flavored liqueur that is consumed in most Mediterranean countries. It is colorless, and because it contains sugar, is sweeter than dry anise flavoured spirits (e.g. absinthe). The most traditional style of anisette ...

and

absinthe Absinthe (, ) is an anise-flavoured spirit derived from several plants, including the flowers and leaves of '' Artemisia absinthium'' ("grand wormwood"), together with green anise, sweet fennel, and other medicinal and culinary herbs. Historica ...

, among others. It is also used in seasoning and confectionery applications, oral hygiene products, and in small quantities in natural berry flavors.

Precursor to other compounds

Because they metabolize anethole into several

aromatic chemical compound Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping ...

s, some bacteria are candidates for use in commercial

bioconversion Bioconversion, also known as ''biotransformation'', is the conversion of organic materials, such as plant or animal waste, into usable products or energy sources by biological processes or agents, such as certain microorganisms. One example is the i ...

of anethole to more valuable materials. Bacterial strains capable of using trans-anethole as the sole carbon source include JYR-1 (''

Pseudomonas putida ''Pseudomonas putida'' is a Gram-negative, rod-shaped, saprotrophic soil bacterium. Based on 16S rRNA analysis, ''P. putida'' was taxonomically confirmed to be a ''Pseudomonas'' species (''sensu stricto'') and placed, along with several other ...

'') and TA13 (''

Arthrobacter aurescens ''Paenarthrobacter aurescens'' is a bacterium species from the genus '' Paenarthrobacter ''. ''Paenarthrobacter aurescens'' produces nitrilase and L-N-carbamoylase. ''Paenarthrobacter aurescens'' has a low GC-content and has the ability to ut ...

'').

Research

Antimicrobial and antifungal activity

Anethole has potent

antimicrobial An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...

properties, against

bacteria Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were am ...

yeast Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constit ...

s, and

fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately fr ...

. Reported antibacterial properties include both

bacteriostatic A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfect ...

and

bactericidal A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on the ...

action against ''

Salmonella enterica ''Salmonella enterica'' (formerly ''Salmonella choleraesuis'') is a rod-headed, flagellate, facultative anaerobic, Gram-negative bacterium and a species of the genus ''Salmonella''. A number of its serovars are serious human pathogens. Epidemi ...

'' but not when used against ''Salmonella'' via a

fumigation Fumigation is a method of pest control or the removal of harmful micro-organisms by completely filling an area with gaseous pesticides—or fumigants—to suffocate or poison the pests within. It is used to control pests in buildings ( ...

method. Antifungal activity includes increasing the effectiveness of some other

phytochemical Phytochemicals are chemical compounds produced by plants, generally to help them resist fungi, bacteria and plant virus infections, and also consumption by insects and other animals. The name comes . Some phytochemicals have been used as poison ...

s (such as

polygodial Polygodial is chemical compound found in dorrigo pepper, mountain pepper, horopito, canelo, paracress, water-pepper, and '' Dendrodoris limbata''.M Jonassohn (1996)Sesquiterpenoid unsaturated dialdehydes - Structural properties that affect re ...

) against ''

Saccharomyces cerevisiae ''Saccharomyces cerevisiae'' () (brewer's yeast or baker's yeast) is a species of yeast (single-celled fungus microorganisms). The species has been instrumental in winemaking, baking, and brewing since ancient times. It is believed to have b ...

'' and ''

Candida albicans ''Candida albicans'' is an opportunistic pathogenic yeast that is a common member of the human gut flora. It can also survive outside the human body. It is detected in the gastrointestinal tract and mouth in 40–60% of healthy adults. It is usu ...

''; ''

In vitro ''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology a ...

'', anethole has

antihelmintic Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may ...

action on eggs and larvae of the

sheep Sheep or domestic sheep (''Ovis aries'') are domesticated, ruminant mammals typically kept as livestock. Although the term ''sheep'' can apply to other species in the genus '' Ovis'', in everyday usage it almost always refers to domesticate ...

gastrointestinal

nematode The nematodes ( or grc-gre, Νηματώδη; la, Nematoda) or roundworms constitute the phylum Nematoda (also called Nemathelminthes), with plant- parasitic nematodes also known as eelworms. They are a diverse animal phylum inhabiting a bro ...

Haemonchus contortus ''Haemonchus contortus'', also known as the barber's pole worm, is a very common parasite and one of the most pathogenic nematodes of ruminants. Adult worms attach to abomasal mucosa and feed on the blood. This parasite is responsible for anemia ...

''. Anethole also has nematicidal activity against the plant nematode ''

Meloidogyne javanica ''Meloidogyne javanica'' is a species of plant-pathogenic nematodes. It is one of the tropical root-knot nematodes and a major agricultural pest in many countries. It has many hosts. ''Meloidogyne javanica'' reproduces by obligatory mitotic part ...

'' in vitro and in pots of

cucumber seedlings Cucumber (''Cucumis sativus'') is a widely-cultivated creeping vine plant in the Cucurbitaceae family that bears usually cylindrical fruits, which are used as culinary vegetables.

Insecticidal activity

Anethole also is a promising insecticide. Several essential oils consisting mostly of anethole have

insecticidal Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed t ...

action against

larva A larva (; plural larvae ) is a distinct juvenile form many animals undergo before metamorphosis into adults. Animals with indirect development such as insects, amphibians, or cnidarians typically have a larval phase of their life cycle. ...

e of the

mosquito Mosquitoes (or mosquitos) are members of a group of almost 3,600 species of small flies within the family Culicidae (from the Latin ''culex'' meaning " gnat"). The word "mosquito" (formed by ''mosca'' and diminutive ''-ito'') is Spanish for "li ...

Ochlerotatus ''Ochlerotatus'' is a genus of mosquito. Until 2000, it was ranked as a subgenus of ''Aedes'', but after Reinert's work, the clade was upgraded to the level of a genus. This change has resulted in the renaming of many subgenus species, and many a ...

caspius'' and ''

Aedes aegypti ''Aedes aegypti'', the yellow fever mosquito, is a mosquito that can spread dengue fever, chikungunya, Zika fever, Mayaro and yellow fever viruses, and other disease agents. The mosquito can be recognized by black and white markings on its l ...

''. In a similar manner, anethole itself is effective against the

fungus gnat Fungus gnats are small, dark, short-lived gnats, of the families Sciaridae, Diadocidiidae, Ditomyiidae, Keroplatidae, Bolitophilidae, and Mycetophilidae (order Diptera); they comprise six of the seven families placed in the superfamily Sc ...

''Lycoriella ingenua'' (

Sciaridae The Sciaridae are a family of flies, commonly known as dark-winged fungus gnats. Commonly found in moist environments, they are known to be a pest of mushroom farms and are commonly found in household plant pots. This is one of the least studie ...

) and the

mold mite ''Tyrophagus putrescentiae'' is a cosmopolitan distribution, cosmopolitan mite species. Together with the related species ''Tyrophagus longior, T. longior'', it is commonly referred to as the mould mite or the cheese mite. The name translates from ...

''Tyrophagus putrescentiae''. Against the mite, anethole is a slightly more effective

pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and ...

than

DEET ''N'',''N''-Diethyl-''meta''-toluamide, also called DEET () or diethyltoluamide, is the most common active ingredient in insect repellents. It is a slightly yellow oil intended to be applied to the skin or to clothing and provides protection a ...

, but

anisaldehyde 4-Anisaldehyde, or ''p''-Anisaldehyde, is an organic compound with the formula CH3OC6H4CHO. The molecule consists of a benzene ring with an formyl and a methoxy group. It is a colorless liquid with a strong aroma. It provides sweet, floral and ...

, a related natural compound that occurs with anethole in many essential oils, is 14 times more effective. The insecticidal action of anethole is greater as a fumigant than as a contact agent. ''trans''-Anethole is highly effective as a fumigant against the

cockroach Cockroaches (or roaches) are a paraphyletic group of insects belonging to Blattodea, containing all members of the group except termites. About 30 cockroach species out of 4,600 are associated with human habitats. Some species are well-known ...

Blattella germanica The German cockroach (''Blattella germanica''), colloquially known as the croton bug, is a species of small cockroach, typically about long. In color it varies from tan to almost black, and it has two dark, roughly parallel, streaks on the prono ...

'' and against adults of the

weevil Weevils are beetles belonging to the superfamily Curculionoidea, known for their elongated snouts. They are usually small, less than in length, and herbivorous. Approximately 97,000 species of weevils are known. They belong to several families, ...

s '' Sitophilus oryzae'', ''

Callosobruchus chinensis ''Callosobruchus chinensis'' is a common species of beetle found in the bean weevil subfamily, and is known to be a pest to many stored legumes. Although it is commonly known as the adzuki bean weevil it is in fact not a true weevil, belonging in ...

'' and

beetle Beetles are insects that form the order Coleoptera (), in the superorder Endopterygota. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 400,000 describ ...

Lasioderma serricorne ''Lasioderma serricorne'', commonly known as the cigarette beetle, cigar beetle, or tobacco beetle, is an insect very similar in appearance to the drugstore beetle (''Stegobium paniceum'') and the common furniture beetle (''Anobium punctatum''). ...

''. As well as an insect pesticide, anethole is an effective

insect repellent An insect repellent (also commonly called "bug spray") is a substance applied to skin, clothing, or other surfaces to discourage insects (and arthropods in general) from landing or climbing on that surface. Insect repellents help prevent and cont ...

against mosquitos.

Ouzo effect

Anethole is responsible for the " ouzo effect" (also "louche effect"), the spontaneous formation of a

microemulsion Microemulsions are clear, thermodynamically stable isotropic liquid mixtures of oil, water and surfactant, frequently in combination with a cosurfactant. The aqueous phase may contain salt(s) and/or other ingredients, and the "oil" may actually be ...

that gives many alcoholic beverages containing anethole and water their cloudy appearance. Such a spontaneous microemulsion has many potential commercial applications in the food and pharmaceutical industries.

Precursor to illicit drugs

Anethole is an inexpensive chemical precursor for

paramethoxyamphetamine ''para''-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or enta ...

(PMA), and is used in its clandestine manufacture. Anethole is present in the essential oil from

guarana Guaraná ( from the Portuguese ''guaraná'' ), ''Paullinia cupana'', syns. ''P. crysan, P. sorbilis'') is a climbing plant in the family Sapindaceae, native to the Amazon basin and especially common in Brazil. Guaraná has large leaves and cl ...

, which has psychoactive effects typically attributed to its caffeine content. The absence of PMA or any other known psychoactive derivative of anethole in human urine after ingestion of guarana leads to the conclusion that any psychoactive effect of guarana is not due to aminated anethole metabolites. Anethole is also present in

, a

liquor Liquor (or a spirit) is an alcoholic drink produced by distillation of grains, fruits, vegetables, or sugar, that have already gone through alcoholic fermentation. Other terms for liquor include: spirit drink, distilled beverage or h ...

with a reputation for

psychoactive A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. Th ...

effects; these effects, however, are attributed to

. (See also

thujone Thujone () is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone. Though it is best known as a chemical compound in the spirit absinthe, it is unlikely to be responsib ...

anethole dithione Anethole trithione, anetholtrithione, or anetholtrithion ( JAN) is a drug used in the treatment of dry mouth. It is listed in the U.S. National Cancer Institute's ''Dictionary of Cancer Terms'' as being studied in the treatment of cancer.

(ADT), and

anethole trithione Anethole trithione, anetholtrithione, or anetholtrithion ( JAN) is a drug used in the treatment of dry mouth. It is listed in the U.S. National Cancer Institute's ''Dictionary of Cancer Terms'' as being studied in the treatment of cancer.

(ATT).)

Estrogen and prolactin

Anethole has

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal ac ...

ic activity. It has been found to significantly increase

uterine The uterus (from Latin ''uterus'', plural ''uteri'') or womb () is the organ in the reproductive system of most female mammals, including humans that accommodates the embryonic and fetal development of one or more embryos until birth. The ...

weight in immature female rats. Fennel, which contains anethole, has been found to have a galactagogue effect in animals. Anethole bears a structural resemblance to

catecholamine A catecholamine (; abbreviated CA) is a monoamine neurotransmitter, an organic compound that has a catechol (benzene with two hydroxyl side groups next to each other) and a side-chain amine. Catechol can be either a free molecule or a su ...

s like

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 80% o ...

and may displace dopamine from its receptors and thereby disinhibit

prolactin Prolactin (PRL), also known as lactotropin, is a protein best known for its role in enabling mammals to produce milk. It is influential in over 300 separate processes in various vertebrates, including humans. Prolactin is secreted from the pi ...

secretion, which in turn may be responsible for the galactagogue effects.

Safety

In the USA, anethole is generally recognized as safe (GRAS). After a hiatus due to safety concerns, anethole was reaffirmed by

Flavor and Extract Manufacturers Association The Flavor and Extract Manufacturers Association (FEMA) is a food industry trade group based in the United States. FEMA was founded in 1909 by several flavor firms in response to the passage of the Pure Food and Drug Act of 1906. Founding members ...

(FEMA) as GRAS. The concerns related to liver toxicity and possible carcinogenic activity reported in rats. Anethole is associated with a slight increase in

liver cancer Liver cancer (also known as hepatic cancer, primary hepatic cancer, or primary hepatic malignancy) is cancer that starts in the liver. Liver cancer can be primary (starts in liver) or secondary (meaning cancer which has spread from elsewhere to th ...

in rats, although the evidence is scant and generally regarded as evidence that anethole is ''not'' a

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive sub ...

. An evaluation of anethole by the

Joint FAO/WHO Expert Committee on Food Additives The Joint FAO/WHO Expert Committee on Food Additives (JECFA) is an international scientific expert committee that is administered jointly by the Food and Agriculture Organization of the United Nations (FAO) and the World Health Organization (WHO). ...

(JECFA) found its notable pharmacologic properties to be reduction in motor activity, lowering of

body temperature Thermoregulation is the ability of an organism to keep its body temperature within certain boundaries, even when the surrounding temperature is very different. A thermoconforming organism, by contrast, simply adopts the surrounding temperatur ...

, and

hypnotic Hypnotic (from Greek ''Hypnos'', sleep), or soporific drugs, commonly known as sleeping pills, are a class of (and umbrella term for) psychoactive drugs whose primary function is to induce sleep (or surgical anesthesiaWhen used in anesthesia ...

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

, and

anticonvulsant Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of ...

effects. A subsequent evaluation by JECFA found some reason for concern regarding carcinogenicity, but there is currently insufficient data to support this. At this time, the JECFA summary of these evaluations is that anethole has "no safety concern at current levels of intake when used as a flavoring agent". In large quantities, anethole is slightly

toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a sub ...

and may act as an irritant.

History

That an oil could be extracted from anise and fennel had been known since the

Renaissance The Renaissance ( , ) , from , with the same meanings. is a period in European history marking the transition from the Middle Ages to modernity and covering the 15th and 16th centuries, characterized by an effort to revive and surpass ide ...

by the German alchemist

Hieronymus Brunschwig Hieronymus Brunschwig or Hieronymus Brunschwygk (c. 1450c. 1512) was a German surgeon ("Wundarzt"), alchemist and botanist. He was notable for his methods of treatment of gunshot wounds and for his early work on distillation techniques. His most i ...

(), the German botanist

Adam Lonicer Adam Lonicer, Adam Lonitzer or Adamus Lonicerus (10 October 1528 – 29 May 1586) was a German botanist, noted for his 1557 revised version of Eucharius Rösslin's herbal. Lonicer was born in Marburg, the son of a theologian and philologist. He ...

(1528–1586), and the German physician

Valerius Cordus Valerius Cordus (18 February 1515 – 25 September 1544) was a German physician, botanist and pharmacologist who authored the first pharmacopoeia North of the Alps and one of the most celebrated herbals in history. He is also widely credited ...

(1515–1544), among others.See: * * * Anethole was first investigated chemically by the Swiss chemist Nicolas-Théodore de Saussure in 1820. In 1832 the French chemist

Jean Baptiste Dumas Jean Baptiste André Dumas (14 July 180010 April 1884) was a French chemist, best known for his works on organic analysis and synthesis, as well as the determination of atomic weights (relative atomic masses) and molecular weights by measuring v ...

determined that the crystallizable components of anise oil and fennel oil were identical, and he determined anethole's empirical formula. In 1845, the French chemist Charles Gerhardt coined the term ''anethol'' – from the Latin ''anethum'' (anise) + ''oleum'' (oil) – for the fundamental compound from which a family of related compounds was derived. Although the German chemist

Emil Erlenmeyer Richard August Carl Emil Erlenmeyer (28 June 182522 January 1909), known simply as Emil Erlenmeyer, was a German chemist known for contributing to the early development of the theory of structure, formulating the Erlenmeyer rule, and designing ...

proposed the correct molecular structure for anethole in 1866, it was not until 1872 that the structure was accepted as correct.

References

External links

* {{Estrogenics Flavors Sugar substitutes Essential oils Phenylpropenes O-methylated natural phenols Estrogens