Citronellyl acetate

Synthesis route :

Citronellyl acetate can be synthesized by an esterification reaction between Citronellol and acetic acid or acetic anhydride, in an acid medium. It can also be synthesized from 3,7-dimethylocta-1,6-diene, obtained naturally by pyrolysis of alpha-Pinene. This synthesis is made in three steps: a Markovnikov addition reaction using hydrochloric acid, a Kharasch reaction, also called anti-Markovnikov reaction, with hydrobromic acid, followed by an acetolysis reaction using sodium ethanoate.

Synthesis precursor :

Citronellyl acetate is not a precursor to the synthesis of another compound of olfactory interest.

Isomerism :

The asymmetric carbon of Citronellol gives it two different smells if its enantiomers are separated: the (R)-(+)-Citronellyl acetate is fruity and rosy, while the (S)-(-)-Citronellyl acetate is more aldehydic, dirty and lemony. In perfumery, those two enantiomers can be used separately. In most cases, a mixture of the two is used. Menthanyl acetate, Verdox® and Vertenex® are constitutional isomers of Citronellyl acetate. However, Menthanyl acetate is much more reminiscent of Bergamot EO, and Verdox® and Vertenex® are woodier.