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α-Myrcene

From Wikipedia, the free encyclopedia
α-Myrcene
Names
IUPAC name
2-Methyl-6-methylideneocta-1,7-diene
Other names
alpha-Myrcene
Identifiers
3D model (JSmol)
  • InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5H,1-2,4,6-8H2,3H3
    Key: VYBREYKSZAROCT-UHFFFAOYSA-N
  • C=CC(=C)CCCC(=C)C
Properties
C10H16
Molar mass 136.238 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

α-Myrcene is a monoterpene that is an uncommon[1] isomer of β-myrcene. It has been found in the essential oils of a few species, such as the Balkan Pine[2] and lemongrass.[3]

It differs from the β isomer by the position of one of the three alkene units. The two chemicals can be synthesized in a 3:1 α:β isomeric ratio by pyrolysis of the acetate ester of myrcenol.[4]

References

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  1. ^ Behr, Arno; Johnen, Leif (2009). "Myrcene as a Natural Base Chemical in Sustainable Chemistry: A Critical Review". ChemSusChem. 2 (12): 1072–1095. Bibcode:2009ChSCh...2.1072B. doi:10.1002/cssc.200900186. PMID 20013989.1072-1095&rft.date=2009&rft_id=info:pmid/20013989&rft_id=info:doi/10.1002/cssc.200900186&rft_id=info:bibcode/2009ChSCh...2.1072B&rft.aulast=Behr&rft.aufirst=Arno&rft.au=Johnen, Leif&rfr_id=info:sid/en.wikipedia.org:Α-Myrcene" class="Z3988">
  2. ^ Koukos, P. K.; Papadopoulou, K. I.; Patiaka, D. Th.; Papagiannopoulos, A. D. (2000). "Chemical Composition of Essential Oils from Needles and Twigs of Balkan Pine ( Pinus peuce Grisebach) Grown in Northern Greece". Journal of Agricultural and Food Chemistry. 48 (4): 1266–1268. Bibcode:2000JAFC...48.1266K. doi:10.1021/jf991012a. PMID 10775383.1266-1268&rft.date=2000&rft_id=info:pmid/10775383&rft_id=info:doi/10.1021/jf991012a&rft_id=info:bibcode/2000JAFC...48.1266K&rft.aulast=Koukos&rft.aufirst=P. K.&rft.au=Papadopoulou, K. I.&rft.au=Patiaka, D. Th.&rft.au=Papagiannopoulos, A. D.&rfr_id=info:sid/en.wikipedia.org:Α-Myrcene" class="Z3988">
  3. ^ Desai, Meghal A.; Parikh, Jigisha (2015). "Extraction of Essential Oil from Leaves of Lemongrass Using Microwave Radiation: Optimization, Comparative, Kinetic, and Biological Studies". ACS Sustainable Chemistry & Engineering. 3 (3): 421–431. doi:10.1021/sc500562a.421-431&rft.date=2015&rft_id=info:doi/10.1021/sc500562a&rft.aulast=Desai&rft.aufirst=Meghal A.&rft.au=Parikh, Jigisha&rfr_id=info:sid/en.wikipedia.org:Α-Myrcene" class="Z3988">
  4. ^ Mitzner, B. M.; Theimer, E. T.; Steinbach, L.; Wolt, J. (1965). "α-Myrcene (2-Methyl-6-methylene-1,7-octadiene)". The Journal of Organic Chemistry. 30 (2): 646–648. doi:10.1021/jo01013a505.646-648&rft.date=1965&rft_id=info:doi/10.1021/jo01013a505&rft.aulast=Mitzner&rft.aufirst=B. M.&rft.au=Theimer, E. T.&rft.au=Steinbach, L.&rft.au=Wolt, J.&rfr_id=info:sid/en.wikipedia.org:Α-Myrcene" class="Z3988">