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Myrcene, also known as β-myrcene, is a type of monoterpene characterized by its status as a colorless oil. It is found extensively in essential oils and is primarily produced semi-synthetically from a plant called Myrcia, which is the origin of its name. Notably, myrcene plays a key role as an intermediate in the creation of various fragrances. The isomer of myrcene, α-myrcene (2-methyl-6-methylene-1,7-octadiene), is not naturally occurring and is distinct from β-myrcene. In the perfumery industry, myrcene is valued not so much for its direct use – due to its pleasant but rarely used odor – but more as an important intermediate in the preparation of a variety of flavor and fragrance chemicals. These include well-known compounds like menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. Myrcene is particularly unstable in air, tending to polymerize, and is usually stabilized with additives like alkylphenols or tocopherol. An interesting transformation of myrcene involves its conversion to myrcenol, another fragrant compound found in lavender. This conversion is achieved through a process involving hydroamination of the 1,3-diene with diethylamine, followed by hydrolysis and palladium-catalyzed removal of the amine. Myrcene and myrcenol both participate in Diels-Alder reactions with various dienophiles, such as acrolein. These reactions yield cyclohexene derivatives that are also valued for their use in fragrances, for example, Lyral, which is a well-known fragrance compound. Apart from its use in the fragrance industry, myrcene contributes to the aroma profile of beer, imparting a peppery and balsam-like aroma. This diversity in applications highlights the importance of myrcene in various industries, particularly in the production of flavors and fragrances.

GHS Hazard Statements

• H226 (99.82%): Flammable liquid and vapor [Warning Flammable liquids]

• H304 (98.98%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

• H315 (85.44%): Causes skin irritation [Warning Skin corrosion/irritation]

• H319 (85.44%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

• H400 (11.6%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

• H412 (17.94%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

First Aid

• Inhalation: Seek medical help immediately. Move the affected person to fresh air. If they are not breathing, perform artificial respiration. If breathing is labored, administer oxygen.

• Skin: Wash the affected area thoroughly with soap and a large amount of water.

• Eyes: Rinse the eyes promptly and extensively with water, making sure to keep the eyelids open to ensure thorough flushing.

These instructions are outlined in the Chemical Hazard Response Information System (CHRIS) guidelines by the U.S. Coast Guard.

Chemical and Physical Properties

Source: PubChem