Cinnamyl formate has a balsamic, fruital-floral odor and bittersweet taste reminiscent of apple.
Reported found in narcissus.
Cinnamyl formate is used in trace amounts in flavor compositions, particularly Apple, Banana, Cherry,Pear, Spice, etc. It is particularly interesting in imitation Banana, where it can produce true-to-Nature notes if used discretely, and perhaps in combination with Mimosa absolute, also in traces.
By esterification of cinnamyl alcohol with formic acid.
Detection at 1.0%: cinnamon spicy, slightly balsamic, cherry fruity with berry and tropical nuances.
Taste characteristics at 5 ppm: sweet, cinnamon-like, astringent, with woody resinous and balsamic nuances.
Cinnamyl formate is an α,β-unsaturatedester that can be used as a flavoring agent and a fragrance ingredient.
Flammability and Explosibility
Not classified
Moderately toxic by
ingestion. See also ESTERS. Combustible
liquid. When heated to decomposition it
emits acrid smoke and irritating fumes.
To a flame-dried flask equipped with a stir bar and activated molecular sieves, IMes-HCl (A1-HCl, 6.8 mg, 0.02 mmol) and toluene (2 mL) were added under an inert atmosphere. A toluene solution of 0.5 M KHMDS (0.04 mL) was slowly added to the stirring suspension with continuous stirring for 15 min. Subsequently, a toluene (2 mL) solution of cinnamyl alcohol (1 mmol) and methyl formate (600 mg, 10 mmol) was added, the flask was sealed, and the reaction was heated for 16 hours at 45 °C. Upon completion of the reaction, the crude product was directly sampled onto a silica gel column for purification, resulting in cinnamyl formate.
Cinnamyl formate is hydrolysed by porcine pancreatic lipase 2.6 times more rapidly than is cinnamyl oleate under identical conditions (Brockerhoff, 1970).
[1] Synthesis (Germany), 2017, vol. 49, # 15, p. 3505 - 3510
