cis-3-Hexenyl Acetate

Description

cis-3-Hexen-1 -y 1-acetate has a powerful green, floral note reminiscent of banana. It may be prepared by acetylation of the corresponding alcohol.

Chemical properties

Colorless liquid

Chemical properties

(Z)-3-Hexenyl Acetate has been identified in many fruit aromas and green tea. It is a prototype for green odors and is often used in combination with (Z)-3-hexenol.

Chemical properties

cis-3-Hexen-1-yl acetate has a powerful, green, fruity, floral note reminiscent of banana.

Occurrence

Reported found in apple, bilberry, guava, strawberry, black and green tea, yellow and purple passion fruit, citrus peel oils, melon, peach, raspberry, pear, pineapple, melon, celery, tomato, corn mint oil, spearmint oil, brandies, grape wines, soybeans, olive, plum, plumcot, starfruit, mango, cauliflower, dill, lovage, corn oil, nectarines, Chinese quince and chamomile oil.

The Uses of cis-3-Hexenyl Acetate

Leaf Acetate increased leaf-feeding herbivores’ egg predation rates by a generalist predator. As a consequence, a plant could reduce the number of herbivores by more than 90% by releasing volatiles.

Definition

ChEBI: An acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol.
In dilutions below 10 ppm, it produces very pleasant fruity-green flavours, and its taste individually at concentrations below 2 ppm is distinctly Banana-1ike. Very interesting combination flavors can be created with this ester and a few other chemicals: A concentration of about 1 ppm of cis-3-Hexenyl acetate in the presence of 0.05 ppm Allyl-iso-thiocyanate (Allyl mustard oil) will produce a distinct note of unripe Banana with the sharp greenness and the fruity notes unmistakably identifiable as Banana and absolutely no impression of Mustard. The two materials separately at the concentrations indicated give very weak and incomplete flavor pictures. However, this ester finds considerable use in perfumes, where it may lend pleasant and natural freshness to delicate florals (Muguet, Lilac, Narcisse, etc.) and participate in creating true-to-nature, foliage-green topnotes in other fragrance types. The ester is most likely to supersede the less stable and less natural-smelling Alkyl acetylenic esters, slowly being abandoned in modern perfumery.

Preparation

By acetylation of the corresponding alcohol

Taste threshold values

Taste characteristics at 10 ppm: green, fruity, apple and pear with fresh tropical nuances

Synthesis Reference(s)

Canadian Journal of Chemistry, 65, p. 2327, 1987 DOI: 10.1139/v87-388

Flammability and Explosibility

Flammable