Clear colorless to yellowish crystalline mass or liquid after meltin
Benzyl cinnamate has a sweet, balsamic odor and a honey-like taste.
Benzyl Cinnamate occurs in
balsams and balsam oils. It forms white, sweet-balsamic-smelling crystals (mp
35-36°C). Benzyl cinnamate is used as a fixative in perfumes and as a component
of heavy, oriental perfumes.
Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of
copaiba balsam.
Benzyl cinnamate has been employed as internal standard during the determination of compounds commonly added to personal care products such as UV filters and antimicrobial agents in environmental samples.
Mild. sweet-balsamic and somewhat floral
odor of great tenacity. Used quite frequently in perfumery, mainly
as a fixative, and particularly in perfumes for Talcum (powders). It blends well with floral
bases, spicy fragrances and Ambre types.
Used in flavor compositions for imitation
Apricot, Cherry, Chocolate, Honey, Peach,
Pineapple, Liquor, Raspberry, Rum, Prune,
etc.
Concentration may be little more than
traces, usually about 6 ppm, except in chewing
gum: up to 125 ppm.
ChEBI: Benzyl cinnamate is the cinnamate ester derived from cinnamic acid and benzyl alcohol. Occuring in Balsam of Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam, it is used in heavy oriental perfumes, as a fixative and as a flavouring agent. It has a role as a flavouring agent, a fragrance, a fixative, an antigen and an epitope.
Benzyl cinnamate is produced by the direct esterification of
benzyl alcohol with cinnamic acid.
By heating benzyl chloride and excess sodium cinnamate in water to 100 to 115°C; by heating sodium cinnamate with an
excess of benzyl chloride in the presence of diethylamine.
Taste characteristics at 50 ppm: spicy, floral, fruity, balsamic.
Benzyl cinnamate is widely used as a fragrance ingredient.
Flammability and Explosibility
Non flammable
Moderately toxic by ingestion. Amild allergen and skin irritant. Combustible liquid. When heated to decomposition it emits acridsmoke and irritating fumes.
Immunology & Inflammation related
See monograph on Benzyl alcohol (p. 1011).
Recrystallise the ester to a constant melting point from 95% EtOH. It has the odour of balsam. Alternatively dissolve it in Et2O, wash it with 10% aqueous Na2CO3, H2O, dry (Na2SO4), evaporate and fractionate it under reduced pressure using a short Vigreux column (p 11). It decomposes when boiled at atmospheric pressure. [Eliel & Anderson J Am Chem Soc 74 547 1952, Bender & Zerner J Am Chem Soc 84 2550 1962, Beilstein 9 IV 2012.]
