Myrcenol

Myrcenol

Names
Preferred IUPAC name 2-Methyl-6-methylideneoct-7-en-2-ol
Identifiers
CAS Number	543-39-5  Y
3D model (JSmol)	Interactive image
ChemSpider	10510  N
ECHA InfoCard	100.008.040
PubChem CID	10975
UNII	X4XS5MYJ20  Y
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 N Key: DUNCVNHORHNONW-UHFFFAOYSA-N 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	154.253 g·mol−1
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). N  verify  (what is  YN ?) 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 formed upon boiling hops ( Humulus lupulus ). ^[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

1. Zanoli, Paola; Zavatti, Manuela (2008). "Pharmacognostic and pharmacological profile of Humulus lupulus L". Journal of Ethnopharmacology. 116 (3): 383–396. doi:10.1016/j.jep.2008.01.011. PMID   18308492.
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