Myrcenol

Myrcenol
Names
	Preferred IUPAC name 2-Methyl-6-methylideneoct-7-en-2-ol
Identifiers
CAS Number	543-39-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	10510 ;
ECHA InfoCard	100.008.040
PubChem CID	10975;
UNII	X4XS5MYJ20 ;
CompTox Dashboard (EPA)	DTXSID5027192 ;
	InChI InChI=1S/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3 Key: DUNCVNHORHNONW-UHFFFAOYSA-N ; InChI=1/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3 Key: DUNCVNHORHNONW-UHFFFAOYAC;
	SMILES C=CC(=C)CCCC(C)(C)O;
Properties
Chemical formula	C10H18O
Molar mass	154.24 g/mol
Density	0.85 g/cm3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

It is also found in the hop plant (Humulus lupulus). E-Myrcenol acts also as a pheromone for bark beetles.^[1]

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-diene, myrcenol undergoes Diels-Alder reactions with several dienophiles such as acrolein to give cyclohexene derivatives that are also useful fragrances.^[2]

References

^ 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.
^ 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

[1] 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.

[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

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