α-Myrcene

α-Myrcene
Names
	IUPAC name 2-Methyl-6-methylideneocta-1,7-diene
	Other names alpha-Myrcene
Identifiers
CAS Number	1686-30-2;
3D model (JSmol)	Interactive image;
ChemSpider	452986;
PubChem CID	519324;
CompTox Dashboard (EPA)	DTXSID50333971 ;
	InChI InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5H,1-2,4,6-8H2,3H3 Key: VYBREYKSZAROCT-UHFFFAOYSA-N;
	SMILES C=CC(=C)CCCC(=C)C;
Properties
Chemical formula	C10H16
Molar mass	136.238 g·mol−1
Appearance	colorless liquid
Density	0.7959 g/cm3
Boiling point	44 °C (111 °F; 317 K) 10 mm Hg
Refractive index (nD)	1.4661
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

α-Myrcene is an organic compound with the formula CH₂=C(CH₃)CH₂CH₂CH₂C(=CH₂)CH=CH₂. It is an uncommon monoterpene.^[2] It is isomeric with β-myrcene, both being trienes.

α-Myrcene has been found in the essential oils of a few species, such as the Balkan pine (Pinus peuce)^[3] and lemongrass (Cymbopogon).^[4]

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.^[1]

References

1 2 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.
↑ 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.
↑ 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.
↑ 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.

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[JOC-1] 1 2 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.

[2] 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.

[3] 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.

[4] 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.

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References