DL-citronellyl acetate

Other comments :

Citronellyl acetate has a less green apple note than Geranyl acetate or Neryl acetate. May contain traces of Citronellol and/or Geraniol and therefore a check must be made as it becomes a possible allergen.

Stability :

acetates may form acetic acid through time

Uses in perfumery :

Citronellyl acetate is used for a fruity note in rose, lily of the valley and lavender accords for example.

Year of discovery :

Data not available.

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.

Synthesis precursor :

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

Natural availability :

Citronellyl acetate is naturally present in Lemongrass EO, Geranium EO and Rose de Mai Absolute, and therefore is extractable in order to obtain natural 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.