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Myrcene

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Myrcene
Beta-myrcene, skeletal formula
Beta-myrcene, ball-and-stick model
Names
IUPAC name 7-Methyl-3-methylene-1,6-octadiene
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.203 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3Key: UAHWPYUMFXYFJY-UHFFFAOYSA-N
  • InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,7H,1,4,6,8H2,2-3H3Key: UAHWPYUMFXYFJY-UHFFFAOYAT
SMILES
  • CC(=CCCC(=C)C=C)C
Properties
Chemical formula C10H16
Molar mass 136.238 g·mol
Density 0.794 g/cm
Melting point < -10 °C
Boiling point 166-168 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 and myrcene is one of the most important. It is a component of the essential oil of the several plants including bay, ylang-ylang, wild thyme, 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 is not found in nature and is little used.

Biosynthesis and production

Terpenes arises naturally from dehydration of terpenol geraniol. It could in principle be extract 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.

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 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 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.

Compendial status

Partial list of the plants that contain myrcene

As mentioned above, many plants contain myrcene, sometimes in very large amounts.

References

  1. Merck Index, 11th Edition, 6243
  2. ^ 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
  3. Chyau, Charng-Cherng; Mau, Jeng-Leun; Wu, Chung-May; 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. {{cite journal}}: |access-date= requires |url= (help); Cite has empty unknown parameter: |coauthors= (help); Explicit use of et al. in: |first= (help)
  4. Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010.
  5. ^ Arno, B. and Leif, J., "Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review", ChemSusChem, 2009, volume 2, pp. 1072-1095. doi:10.1002/cssc.200900186
  6. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 31 March 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)

See also

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