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Myrcene[1]
Identifiers
CAS number 123-35-3 Yes check.svgY
SMILES
Properties
Molecular formula C10H16
Molar mass 136.23 g/mol
Density 0.794 g/cm3
Melting point

50 °C

Boiling point

166-168 °C

 Yes check.svgY (what is this?)  (verify)
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, but more precisely as a monoterpene. Terpenes are dimers of isoprene. Myrcene is a component of the essential oil of the several plants including bay, verbena, pinene, and other plants.[2] myrcia (from which is gets its name). It is produced mainly semi-synthetically from It is a key intermediate in the production of several fragrances.

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 polymerise. It is also highly valued as an intermediate for the preparation of flavor and fragrance chemicals such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool.

The pyrolysis of pinene produces myrcene, which is then treated with hydrogen chloride to give 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 hydrolysed 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-catalysed 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.[3]

α-Myrcene is the name for the structural isomer 2-methyl-6-methylene-1,7-octadiene, which is not found in nature.

References

  1. ^ Merck Index, 11th Edition, 6243.
  2. ^ Chyau, Charng-Cherng et al. (1996). "Characteristics of the Steam-Distilled Oil and Carbon Dioxide Extract of Zanthoxylum simulans Fruits". Journal of Agricultural and Food Chemistry 44 (4): 1096 – 1099. doi:10.1021/jf950577d. 
  3. ^ Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg “Flavors and Fragrances” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_141

Appendix: partial list of the plants that contain myrcene








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