Myrcenol
Encyclopedia
Myrcenol is an organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

, specificially a terpenoid
Terpene
Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...

. It is most notable as one of the fragrant components of lavender
Lavender
The lavenders are a genus of 39 species of flowering plants in the mint family, Lamiaceae. An Old World genus, distributed from Macaronesia across Africa, the Mediterranean, South-West Asia, Arabia, Western Iran and South-East India...

 oil.

Role in fragrance industry

Myrcenol is obtained synthetically from myrcene via hydroamination
Hydroamination
The hydroamination reaction is the addition of an N-H bond across the C=C or C≡C bonds of an alkene or alkyne. This is a highly atom economical method of preparing substituted amines that are attractive targets for organic synthesis and the pharmaceutical industry.The hydroamination reaction is...

 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
Acrolein
Acrolein is the simplest unsaturated aldehyde. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity...

 to give cyclohexene derivatives that are also useful fragrances.

It is also found in the hop plant (Humulus lupulus
Humulus lupulus
Humulus lupulus is a species of Humulus in the Cannabaceae family.Common hop is a dioecious, perennial herbaceous climbing plant which sends up new shoots in early spring and dies back to the cold-hardy rhizome in autumn...

). E-Myrcenol acts also as a pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

for bark beetles.
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