Myrcene, or β-myrcene, is a

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...

. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from '' Myrcia'', from which it gets its name. It is an intermediate in the production of several fragrances. α-Myrcene is the name for the isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature.

Production

Myrcene is often produced commercially by the

pyrolysis The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...

(400 °C) of β-

pinene Pinene is a collection of unsaturated bicyclic monoterpenes. Two geometric isomers of pinene are found in nature, α-pinene and β-pinene. Both are chiral. As the name suggests, pinenes are found in pines. Specifically, pinene is the major comp ...

, which 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 spec ...

. It is rarely obtained directly from plants. Plants biosynthesize myrcene via geranyl pyrophosphate (GPP), which isomerizes into linalyl pyrophosphate. The release of the

pyrophosphate In chemistry, pyrophosphates are phosphorus oxyanions that contain two phosphorus atoms in a P–O–P linkage. A number of pyrophosphate salts exist, such as disodium pyrophosphate (Na2H2P2O7) and tetrasodium pyrophosphate (Na4P2O7), among othe ...

(OPP) and a proton completes the conversion.

Occurrence

It could in principle be extracted from any number of plants, such as

verbena ''Verbena'' (), also known as vervain or verveine, is a genus in the family Verbenaceae. It contains about 150 species of annual and perennial herbaceous or semi-woody flowering plants. The majority of the species are native to the Americas a ...

wild thyme ''Thymus serpyllum'', known by the common names of Breckland thyme, Breckland wild thyme, wild thyme, creeping thyme, or elfin thyme, is a species of flowering plant in the mint family Lamiaceae, native to most of Europe and North Africa. It ...

, the leaves of which contain up to 40% by weight of myrcene. Many other plants contain myrcene, sometimes in substantial amounts. Some of these include cannabis, hops, ''

Houttuynia ''Houttuynia'' is a genus of two species in the Saururaceae native to Southeast Asia. One species, '' H. cordata'', is widely cultivated as a culinary herb. The genus was originally described in 1783 by Carl Peter Thunberg when he formally ...

'',

lemon grass ''Cymbopogon'', also known as lemongrass, barbed wire grass, silky heads, Cochin grass, Malabar grass, oily heads, citronella grass or fever grass, is a genus of Asian, African, Australian, and tropical island plants in the grass family. Some s ...

, mango, ''Myrcia'', West Indian bay tree, and

cardamom Cardamom (), sometimes cardamon or cardamum, is a spice made from the seeds of several plants in the genera ''Elettaria'' and ''Amomum'' in the family Zingiberaceae. Both genera are native to the Indian subcontinent and Indonesia. They are r ...

. Of the several terpenes extracted from ''

Humulus lupulus ''Humulus lupulus'', the common hop or hops, is a species of flowering plant in the hemp family Cannabinaceae, native to Europe, western Asia and North America. It is a perennial, herbaceous climbing plant which sends up new shoots in early s ...

'' (hops), the largest monoterpenes fraction is β-myrcene. One study of the chemical composition of the fragrance of ''

Cannabis sativa ''Cannabis sativa'' is an annual herbaceous flowering plant indigenous to Eastern Asia, but now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history, used as a source of industrial fibe ...

'' found β-myrcene to compose between 29.4% and 65.8% of the steam-distilled essential oil for the set of fiber and drug strains tested. Additionally, myrcene is thought to be the predominant terpene found in modern cannabis cultivars within North America. Interestingly, photo-oxidation of myrcene has been shown to rearrange the molecule into a novel terpene known as "hashishene" which is named for its abundance in hashish. It is found in the South African '' Adenandra villosa'' (50%). & Brazilian ''

Schinus molle ''Schinus molle'' (Peruvian pepper, also known as American pepper, Peruvian peppertree, escobilla, false pepper, rosé pepper, molle del Peru, pepper tree, (Archived bWebCite peppercorn tree, California pepper tree, pirul (in Mexican Spanish si ...

'' (40%) Myrcene is also found in '' Myrcia cuprea''

petitgrain Petitgrain () is an essential oil that is extracted from the leaves and green twigs of the bitter orange tree (''Citrus aurantium'' ssp. ''amara'') via steam distillation. It is also known as petitgrain bigarade. Etymology Petitgrain (Fr.: � ...

(up to 48%), bay leaf,

juniper berry A juniper berry is the female seed cone produced by the various species of junipers. It is not a true berry, but a cone with unusually fleshy and merged scales, which gives it a berry-like appearance. The cones from a handful of species, especia ...

cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternative ...

, and hops.

Use in fragrance and flavor industries

Myrcene is an intermediate used in the

perfumery Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

industry. It has a pleasant odor but is rarely used directly. It is also unstable in air, tending to

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

ize. Samples are stabilized by the addition of alkylphenols or

tocopherol Tocopherols (; TCP) are a class of organic chemical compounds (more precisely, various methylated phenols), many of which have vitamin E activity. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rat ...

. It is thus more highly valued as an intermediate for the preparation of flavor and fragrance chemicals, such as menthol,

citral Citral is an acyclic monoterpene aldehyde, and being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the ''E''-isomer is named geranial (''trans' ...

citronellol Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including ''Cymbopogon nardus'' (50%), is the more common isomer. (−)-Citronellol is w ...

citronellal Citronellal or rhodinal ( C10 H18 O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent. Citronellal is a main isolate in distilled oils from the p ...

geraniol Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in w ...

nerol Nerol is a monoterpenoid alcohol found in many essential oils such as lemongrass and hops. It was originally isolated from neroli oil, hence its name. This colourless liquid is used in perfumery. Like geraniol, nerol has a sweet rose odor but it ...

, and

linalool Linalool () refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of ...

. Myrcene is converted to

myrcenol Myrcenol is an organic compound, specifically a terpene, terpenoid. It is most notable as one of the fragrant components of lavender oil. It is also found in the hop plant (''Humulus lupulus''). E-Myrcenol acts also as a pheromone for bark beetles ...

, another fragrance found in

lavender ''Lavandula'' (common name lavender) is a genus of 47 known species of flowering plants in the mint family, Lamiaceae. It is native to the Old World and is found in Cape Verde and the Canary Islands, and from Europe across to northern and easte ...

, via

hydroamination In organic chemistry, hydroamination is the addition of an bond of an amine across a carbon-carbon multiple bond of an alkene, alkyne, diene, or allene. In the ideal case, hydroamination is atom economical and green. Amines are common in fine ...

of the 1,3-diene by diethylamine followed by hydrolysis and

palladium Palladium is a chemical element with the symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1803 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas, which was itself na ...

-catalyzed removal of the

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen Hydrogen is the chemical element wi ...

. Both myrcene and myrcenol undergo Diels-Alder reactions with several dienophiles such as acrolein to give

cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light a ...

derivatives that are also useful fragrances, for instance

Lyral Hydroxymethylpentylcyclohexenecarboxaldehyde is a synthetic fragrance known by the trade names Lyral, Kovanol, Mugonal, Landolal. It is found in some soaps, eau de toilettes, aftershaves and deodorant A deodorant is a substance applied to the ...

. Myrcene also contributes a peppery and balsam aroma in beer. As of October 2018, the U.S. FDA withdrew authorization for the use of myrcene as a synthetic flavoring substance for use in food, without regard to its continuing stance that this substance does not pose a risk to public health under the conditions of its intended use.

Health and safety

In 2015, beta-myrcene was added to California's Prop 65 list of chemicals known to the state of California to cause cancer or reproductive harm.

References

{{reflist Flavors Polyenes Perfume ingredients Monoterpenes

Production

Occurrence

Use in fragrance and flavor industries

Health and safety

See also

References