Benzyl cinnamate

Chemical properties

Clear colorless to yellowish crystalline mass or liquid after meltin

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

Benzyl cinnamate has a sweet, balsamic odor and a honey-like taste.

Occurrence

Reported found in Peru and Tolu balsam, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam.

The Uses of Benzyl cinnamate

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.

The Uses of Benzyl cinnamate

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.

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.

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.

Taste threshold values

Taste characteristics at 50 ppm: spicy, floral, fruity, balsamic.

General Description

Benzyl cinnamate is widely used as a fragrance ingredient.

Hazard

Moderately toxic.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion. Amild allergen and skin irritant. Combustible liquid. When heated to decomposition it emits acridsmoke and irritating fumes.

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.]