Myrcenol

Myrcenol
IUPAC name 2-methyl-6-methyleen-2,7-octadieen-1-ol
Identifiers
CAS number	543-39-5
PubChem	10975
Jmol-3D images	Image 1
SMILES C=CC(=C)CC\C=C(\C)CO
Properties
Molecular formula	C10H18O
Molar mass	154.24 g/mol
Exact mass	154.135765
Density	0.85 g/cm3
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Myrcenol is an organic compound, specificially a terpenoid. It is most notable as one of the fragrant components of lavender oil.

Role in fragrance industry

Myrcenol is obtained synthetically from myrcene via hydroamination of the 1,3-diene followed by hydrolysis and Pd-catalysed removal of the amine. As a 1,3-dienes, mycenol undergoes Diels-Alder reactions with several dienophiles such as acrolein to give cyclohexene derivatives that are also useful fragrances.^[1]

It is also found in the hop plant (Humulus lupulus). E-Myrcenol acts also as a pheromone for bark beetles^[2].

References

1. ^ 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}}
2. ^ E-Myrcenol in Ips duplicatus: An aggregation pheromone component new for bark beetles. Byers, J.A., Schlyter, F., Birgersson, G., & Francke, W. 1990 Experientia 46:1209-1211.