Cis-3-hexenyl acetate

Other comments :

cis-3-Hexenyl acetate is more aqueous and greener than Hexyl acetate, with no jasmine aspect. It also is less etheric than cis-3-Hexenyl Formate.

Stability :

acetates may form acetic acid through time. Cis-3-Hexenyl acetate is especially unstable in shower gel and shampoo bases.

Uses in perfumery :

cis-3-Hexenyl acetate is used in fruity-pear, apple and banana accords and in floral notes for an aqueous and airy note. Brings a green, aqueous and fruity facet at the same time.

Year of discovery :

Data not available.

Isomerism :

Cis-3-Hexenyl acetate diastereoisomer, trans-3-Hexenyl acetate, has almost identical facets as its smell is green, fruity-pear and banana. Another position isomer, called trans-2-Hexenyl acetate, is also useful in perfumery for a less green but more fruity note, reminiscent of apple and pear. Moreover, cis-3-Hexenyl acetate is a constitutional isomer of delta-Octalactone, although they do not share the same smell and their structure are very different.

Synthesis precursor :

Cis-3-Hexenyl acetate is not a precursor to the synthesis of another compound of olfactory interest.

Natural availability :

Cis-3-Hexenyl acetate is present in the fragrant principle of several fruits such as apple or guava and is also present in hyacinth, Sambac Jasmine Absolute and Ylang-Ylang Extra EO (and other ylang fractions), from which it can be extracted in its natural state in small quantities.

Synthesis route :

Cis-3-Hexenyl acetate results from an esterification of cis-3-Hexenol with acetic acid, in the presence of an acid catalysor as concentrated sulfuric acid. Using acetic anhydride or chloroacetic acid can also enhance the yield of this reaction.