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Myrcenol

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Myrcenol
Names
Preferred IUPAC name 2-Methyl-6-methylideneoct-7-en-2-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.040 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3Key: DUNCVNHORHNONW-UHFFFAOYSA-N
  • InChI=1/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3Key: DUNCVNHORHNONW-UHFFFAOYAC
SMILES
  • C=CC(=C)CCCC(C)(C)O
Properties
Chemical formula C10H18O
Molar mass 154.253 g·mol
Density 0.85 g/cm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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).

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.

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
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