Benzyl cinnamate is the

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

which is the

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

derived from

cinnamic acid Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs na ...

and

benzyl alcohol Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid w ...

Natural occurrence

Benzyl cinnamate occurs in

Balsam of Peru Balsam of Peru or Peru balsam, also known and marketed by many other names, is a balsam derived from a tree known as ''Myroxylon balsamum'' var. ''pereirae''; it is found in El Salvador, where it is an endemic species. Balsam of Peru is used i ...

and

Tolu balsam Tolu balsam or balsam of Tolu is a balsam that originates from South America (Colombia, Peru, Venezuela). It is similar to (and frequently confounded with) the balsam of Peru. It is tapped from the living trunks of ''Myroxylon balsamum var. balsa ...

, in Sumatra and Penang benzoin, and as the main constituent of copaiba balsam. It is used as an ingredient in the medicated cream product Sudocrem.

Synthesis

Benzyl cinnamate can be prepared by heating benzyl chloride and excess sodium cinnamate in water to 100–115 °C or by heating sodium cinnamate with an excess of benzyl chloride in the presence of

diethylamine Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to im ...

Uses

Benzyl cinnamate is used in heavy oriental

perfume Perfume (, ; french: parfum) is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Th ...

s and as a fixative. It is used as a

flavoring A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gus ...

agent. It is used pharmaceutically as an

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...

and antifungal.

References

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External links

Benzyl cinnamate
at

National Library of Medicine The United States National Library of Medicine (NLM), operated by the United States federal government, is the world's largest medical library. Located in Bethesda, Maryland, the NLM is an institute within the National Institutes of Health. Its ...

's Toxicology Data Network Cinnamate esters Perfume ingredients Flavors Benzyl esters