Мірцен

Monoterpenes consist of two isoprene units, and myrcene is classified as an acyclic monoterpene. Myrcene exists in two isomeric forms, β-myrcene and α-myrcene, and the most common is the naturally occurring β-myrcene. Its preferred IUPAC name is 7-methyl-3-methylideneocta-1,6-diene. It can be obtained from Myrcia, from which it gets its name. Myrcia is a genus of plants in the family Myrtaceae, containing about 794 species as of 2025. The genus is distributed in Central and South America, Mexico and the Caribbean, with centres of diversity in the Brazilian Cerrado and Atlantic Forests ecoregions. Plants biosynthesize myrcene via geranyl pyrophosphate, which isomerizes into linalyl pyrophosphate. An elimination reaction, releasing the pyrophosphate and a proton, completes the conversion.

Myrcene occurs naturally in over 200 plants. Some of the plants that contain it are cannabis, hops, Houttuynia, lemon grass, mango, Myrcia, West Indian bay tree and cardamom. It is the major constituent of hop essential oil and can constitute as much as 70% of the essential oil by volume. It is also the major constituent of hop and bay oils, which are used in the manufacture of alcoholic beverages. Myrcene is found in the South African Adenandra villosa (50%) and Brazilian Schinus molle (40%). It could in principle be extracted from plants such as verbena or wild thyme, the leaves of which contain up to 40% by weight of myrcene.

Essential oils that contain myrcene are used as intermediates in the production of terpene alcohols such as geraniol, nerol and linalool, which in turn serve as intermediates in the production of aroma and flavor chemicals. Myrcene reacts with hydrogen chloride to give geranyl chloride, neryl chloride, linalyl chloride and myrcenyl chloride, all of which can be hydrolyzed to the corresponding alcohols. Both myrcene and myrcenol undergo Diels-Alder reactions with several dienophiles, such as acrolein.

Like other conjugated dienes, including other terpenes, myrcene is prone to polymerization. Samples are stabilized by the addition of alkylphenols or tocopherol. Some of these polymers are useful, such as a phenol-myrcene copolymer and resins derived from maleic anhydride.

β-Myrcene has a high production volume, 58,076 kg for Europe and 1,188 kg for the USA. Myrcene, like most terpenes, has very low acute toxicity, estimated to be >5g/kg (oral for rats, rabbits). Exposure to β-myrcene from natural food sources is estimated to be 16,500 times more than from its synthetic use as a flavour substance.

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