MYRCENE
what is MYRCENE?
Synthetic Ingredient For Perfumery Overview
Myrcene, or β-myrcene, is an olefinic natural organic hydrocarbon. It is more precisely classified as a monoterpene. Monoterpenes are dimers of isoprenoid precursors, and 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. It is a key intermediate in the production of several fragrances. 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. It is a colorless or very pale straw-colored mobile liquid. It may acquire a pale amber color and it may eventually resinify (polymerize) upon exposure to daylight and air. Insoluble in water, soluble in alcohol, 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: 7-Methyl-3-methylene-1,6-octadiene
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.
Uses in fragrances and flavors
Myrcene finds use in perfume formulations where its spicy-balsamic and refreshingly light character introduces desirable notes in Citrus and spice colognes (an excellent extender of the odor of Bay leaf oil), or it finds more extensive use in masking odors for industrial purposes, mainly because of its low cost. It is also used as a component of artificial essential oils, and as a fresh note in common household products. It has a pleasant odor but is rarely used directly. It is also unstable in air, tending to polymerize. Samples are stabilized by the addition of alkylphenols or tocopherol. It is thus more highly valued as an intermediate for the preparation of flavour and fragrance chemicals such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. Myrcene also contributes a peppery and balsam aroma in beer.The use as such in perfume compositions is, however, only a drop in the total volume of this terpene manufactured as an intermediate in the production of Terpene alcohols, Citral, ionones, hydroxycitronellal, etc. Trace amounts of Myrcene are used in flavour compositions such as “root-beer’”, Citrus, Coriander, fruit-complexes, etc. The concentration in the finished product will normally be from 0.5 to 5 ppm.
Occurrence
It could in principle be extracted from any number of plants, for example, wild thyme, 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, lemongrass, mango, Myrcia, Verbena, West Indian bay tree, and cardamom. Of the several terpenes extracted from Humulus lupulus (hops), the largest monoterpenes 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
It is produced by the pyrolysis (400 °C) of β-pinene, which is obtained from turpentine. It is rarely obtained directly from plants. Terpenes arise naturally from dehydration of terpenol geraniol. Plants biosynthesize myrcene via geranyl pyrophosphate (GPP)
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.