Nerolidol

Other comments :

Comparing it with other rosy and green notes as Phenoxanol® and Rosacetol®, Nerolidol has a distinctive fruity and green note.

Stability :

Terpenes tend to polymerize by oxydation.

Uses in perfumery :

Nerolidol is used in all types of perfumery for orange, rose, honeysuckle and lily of the valley notes. Useful in citrus and woody-vanillic accords, to give an airy side and make the link between those two facets.

Year of discovery :

Discovered in 1923

Isomerism :

Nerolidol exists as two pairs of enantiomers, as it has an asymmetric carbon and a double bond that gives rise to two diastereoisomers. Synthetic Nerolidol is however a mixture of all these isomers. All have a similar smell, but they do not have the same physicochemical properties.

Synthesis precursor :

Nerolidol can be a precursor to the synthesis of other terpenes, for example by a Diels-Alder reaction. It is also a precursor for the synthesis of Farnesol, following an isomerization process.

Natural availability :

Dextrorotatory trans-Nerolidol is the major compound of cabreuva (84%), a shrub of Paraguay. This same dextrorotatory nerolidol is isolated from Dalbergia parviflora, an Asian liana.

Synthesis route :

Nerolidol is a sesquiterpene, often associated with Linalool, whose synthesis starts from this last compound. Linalool is converted to geranylacetone by reaction with Ethyl Acetoacetate, for example. A condensation of the obtained ketone with acetylene, followed by a Lindlar palladium catalysed hydrogenation allows to obtain Nerolidol.