Benzyl Benzoate

Category

Plasticizer; Solubilizing Agents; Solvent; therapeutic Agents

Molecular Formula

C14H12O2

Molecular Weight

212.24

Grade

Pharmceutical Excipients

Description

Benzyl benzoate is a clear, colorless, oily liquid with a slightly aromatic odor. It produces a sharp, burning sensation on the tongue. At temperatures below 17℃ it exists as clear, colorless crystals.

UNII

N863NB338G

Chemical Name

Benzoic acid phenylmethyl ester

CAS Number

120-51-4

Synonyms

Benzoic acid benzyl ester; benzylbenzenecarboxylate; benzylis benzoas; benzyl phenylformate; phenylmethyl benzoate

Administration route

IM injections and oral

Dosage Form

IM injections and oral capsules

Stability and Storage Conditions

Benzyl benzoate is stable when stored in tight, well-filled, lightresistant containers. Exposure to excessive heat (above 40℃) should be avoided.

Source and Preparation

Benzyl benzoate is a constituent of Peru balsam and occurs naturally in certain plant species. Commercially, benzyl benzoate is produced synthetically by the dry esterification of sodium benzoate and benzoyl chloride in the presence of triethylamine or by the reaction of sodium benzylate with benzaldehyde.

Applications

Benzyl benzoate is used as a solubilizing agent and nonaqueous solvent in intramuscular injections at concentrations of 0.01-46.0% v/v, and as a solvent and plasticizer for cellulose and nitrocellulose. It is also used in the preparation of spray-dried powders using nanocapsules. However, the most widespread pharmaceutical use of benzyl benzoate is as a topical therapeutic agent in the treatment of scabies.Benzyl benzoate is also used therapeutically as a parasiticide in veterinary medicine. Other applications of benzyl benzoate include its use as a pediculicide, and as a solvent and fixative for flavors and perfumes in cosmetics and food products.

Safety

Benzyl benzoate is metabolized by rapid hydrolysis to benzoic acid and benzyl alcohol. Benzyl alcohol is then further metabolized to hippuric acid, which is excreted in the urine. Benzyl benzoate is widely used as a 25% v/v topical application in the treatment of scabies and as an excipient in intramuscular injections and oral products. Adverse reactions to benzyl benzoate include skin irritation and hypersensitivity reactions. Oral ingestion may cause harmful stimulation of the CNS and convulsions. Benzyl benzoate should be avoided by perople with perfume allergy. LD50 (cat, oral): 2.24 g/kg LD50 (dog, oral): 22.44 g/kg LD50 (guinea pig, oral): 1.0 g/kg LD50 (mouse, oral): 1.4 g/kg LD50 (rabbit, oral): 1.68 g/kg LD50 (rabbit, skin): 4.0 g/kg LD50 (rat, oral): 0.5 g/kg LD50 (rat, skin): 4.0 g/kg

Incompatibilities

Benzyl benzoate is incompatible with alkalis and oxidizing agents.