Myrcene
| Myrcene[1] | |
|---|---|
| Beta-myrcene, skeletal formula | |
| Beta-myrcene, ball-and-stick model | |
| 7-Methyl-3-methylene-1,6-octadiene | |
| Identifiers | |
| CAS number | 123-35-3 7px |
| PubChem | 31253 |
| ChemSpider | 28993 7px |
| KEGG | C06074 7px |
| ChEBI | CHEBI:17221 7px |
| ChEMBL | CHEMBL455491 7px |
| Jmol-3D images | Image 1 |
| |
| Molecular formula | C10H16 |
| Molar mass | 136.23 g mol−1 |
| 14px (verify) (what is: 10px/10px?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Myrcene, or β-myrcene, is an olefinic natural organic compound. It is classified as a hydrocarbon, more precisely as a monoterpene. Terpenes are dimers of isoprene, and myrcene is one of the most important. It is a component of the essential oil of several plants including bay, ylang-ylang, wild thyme, and hops.[3][4] 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 is not found in nature and is little used.[5]
Contents
Biosynthesis and production
Terpenes arise naturally from dehydration of terpenol geraniol. 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. The current route to commercial samples is by the pyrolysis (400 °C) of pinene, which is obtained from turpentine.[5]
Use in fragrance industry
Myrcene is an important intermediate used in the perfumery industry. It has 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 flavor and fragrance chemicals such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. Treatment of myrcene with hydrogen chloride gives geranyl chloride, neryl chloride, and linalyl chloride. Treatment of these compounds with acetate gives geranyl acetate, neryl acetate, and linalyl acetate, respectively. These esters are then hydrolyzed to the corresponding alcohols. Myrcene is also converted to myrcenol, another fragrance found in lavender, via uncatalyzed hydroamination of the 1,3-diene followed by hydrolysis and Pd-catalyzed removal of the amine.
As 1,3-dienes, both myrcene and mycenol undergo Diels-Alder reactions with several dienophiles such as acrolein to give cyclohexene derivatives that are also useful fragrances.[2]
Combined Effects
The digestion of Myrcene allows exchange between the blood brain barrier to be increased, Thus allowing A kannibis Connoisseurs "High" to be increased, As cannabis itself contains quantities of Myrcene, which is essentially a limiting factor in the transportation of THC through the blood brain Barrier.[6]
Partial list of the plants that contain myrcene
As mentioned above, many plants contain myrcene, sometimes in very large amounts.[5]
See also
References
- ↑ Merck Index, 11th Edition, 6243
- ↑ 2.0 2.1 Script error
- ↑ Script error
- ↑ Tinseth, G. (January/February 1993). "Hop Aroma and Flavor". Brewing Techniques. http://realbeer.com/hops/aroma.html.
- ↑ 5.0 5.1 5.2 Script error
- ↑ http://forum.grasscity.com/seasoned-tokers/283036-complete-connoisseurs-guide-enjoying-cannabis.html
fa:میرسن it:Mircene lt:Mircenas nl:Myrceen ja:ミルセン pl:Mircen pt:Mirceno ru:Мирцен fi:Myrseeni zh:香叶烯
