Myrcene

Profile:

• 📂 CAS N° 123-35-3

• ⚖️ MW — 136.23 g/mol

• 📝 Odor Type — Fruity

• 📈 Odour Strength — medium

• 👃🏼 Odor Profile — Sweet-balsamic-resinous “gum” odor of poor tenacity. The purified Myrcene is refreshing, almost citrusy, but warm- balsamic, and ethereal-sweet. It is fruity green mango, resinous, and a little bit mushroomy.

• 👅 Flavor Profile — The taste is sweet-balsamic-herbaceous at concentrations below 10 ppm. Higher concentrations tend to give pungency, bitterness and a grassy taste.

Myrcene, or β-myrcene, is an olefinic natural organic hydrocarbon. It is more precisely classified as a monoterpene, which are dimers of isoprenoid precursors. Myrcene is a significant component of the essential oil of several plants, including bay, cannabis, ylang-ylang, wild thyme, parsley, cardamom, and hops. It is produced mainly semi-synthetically from myrcia, from which it gets its name.

Chemical Properties

α-Myrcene is the name for the structural isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature and is little used. Myrcene is a colorless or very pale straw-colored mobile liquid that may acquire a pale amber color and eventually resinify (polymerize) upon exposure to daylight and air. It is insoluble in water, soluble in alcohol, and miscible with most perfume oils. Commercial grades of myrcene may contain up to 20 or 25% of Laevo-Limonene plus minor amounts of beta-Pinene and polymers.

IUPAC Name: 7-Methyl-3-methylene-1,6-octadiene

Uses in Fragrances and Flavors

Myrcene is utilized in perfume formulations where its spicy-balsamic and refreshingly light character introduces desirable notes in citrus and spice colognes. It is an excellent extender of the odor of bay leaf oil and is extensively used in masking odors for industrial purposes due to its low cost. It is also used as a component of artificial essential oils and as a fresh note in common household products.

Despite having a pleasant odor, myrcene is rarely used directly because it is unstable in air and tends to polymerize. Samples are stabilized by adding alkylphenols or tocopherol. Myrcene is highly valued as an intermediate for preparing flavor and fragrance chemicals such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. It contributes a peppery and balsam aroma in beer.

Occurrence

Myrcene can, in principle, be extracted from numerous plants, for example, wild thyme, whose leaves contain up to 40% by weight of myrcene. Many other plants contain myrcene in substantial amounts, including cannabis, hops, Houttuynia, lemongrass, mango, Myrcia, Verbena, West Indian bay tree, and cardamom. Among the several terpenes extracted from Humulus lupulus (hops), the largest monoterpene fraction is β-myrcene. One Swiss study of the chemical composition of the fragrance of Cannabis sativa L. found β-myrcene to comprise between 29.4% to 65.8% of the steam-distilled essential oil for the set of fiber and drug strains tested.

Production

Myrcene is produced by the pyrolysis (400 °C) of β-pinene, obtained from turpentine. It is rarely obtained directly from plants. Terpenes naturally arise from the dehydration of terpenol geraniol. Plants biosynthesize myrcene via geranyl pyrophosphate (GPP).

Conclusion

Myrcene plays a crucial role in the fragrance and flavor industries, not only for its unique aromatic qualities but also as an intermediate in producing other significant chemicals. Its presence in various plants and its semi-synthetic production highlight its versatility and importance.

Source:

• National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 31253, Myrcene. Retrieved November 25, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/Myrcene.