Chemical Properties
Benzyl cinnamate has a sweet, balsamic odor and a honey-like taste.
Chemical Properties
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.
Chemical Properties
Clear colorless to yellowish crystalline mass or liquid after meltin
Occurrence
Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of
copaiba balsam.
Uses
In artificial flavors, in perfumes, mainly as a fixative.
Definition
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.
Preparation
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.
Production Methods
Benzyl cinnamate is produced by the direct esterification of
benzyl alcohol with cinnamic acid.
Taste threshold values
Taste characteristics at 50 ppm: spicy, floral, fruity, balsamic.
General Description
Benzyl cinnamate is widely used as a fragrance ingredient.
Flammability and Explosibility
Nonflammable
Safety Profile
Moderately toxic by ingestion. Amild allergen and skin irritant. Combustible liquid. When heated to decomposition it emits acridsmoke and irritating fumes.
target
Immunology & Inflammation related
Metabolism
See monograph on Benzyl alcohol (p. 1011).
Purification Methods
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.]
