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Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate

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white crystals

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Denatonium benzoate was first synthesized in the 1950s and is usually prepared by reacting denatonium chloride with benzyl benzoate.

Pharmaceutical Applications

Denatonium benzoate is among the most bitter of substances known and is detectable at concentrations of approximately 10 ppb. In pharmaceutical and other industrial applications it is added to some products as a deterrent to accidental ingestion. It is most commonly used at levels of 5–500 ppm. Denatonium benzoate may also be used to replace brucine or quassin as a denaturant for ethanol.
In pharmaceutical formulations, denatonium benzoate has been used as a flavoring agent in placebo tablets, and in a topical formulation it has been used in an anti-nailbiting preparation.

Safety

Denatonium benzoate is generally regarded as a nonirritant and nonmutagenic substance.However,therehasbeenasinglereportof contact urticaria attributed to denatonium benzoate occurring in a 30-year-old man who developed asthma and pruritus after using an insecticidal spray denatured with denatonium benzoate.
LD50 (rabbit, oral): 0.508g/kg
LD50 (rat, oral): 0.584g/kg

Synthesis

A method for synthesizing Denatonium Benzoate comprises the following steps: (1) adding benzyl halide to a reactor containing raw material lidocaine under stirring and at a certain temperature, wherein the reaction temperature is from room temperature to 130°C, and the ratio of lidocaine to benzyl halide is 1:1 to 1:2; (2) after the reaction is complete, adding solvent and metal hydroxide; (3) adding benzoic acid, after the reaction is completed, the generated benzyl ammonium benzoate is filtered, washed, concentrated, and washed to obtain the product benzyl ammonium benzoate.

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Denatonium benzoate is stable up to 140°C and over a wide pH range. It should be stored in a well-closed container (such as polythene-lined steel) in a cool, dry place. Aqueous or alcoholic solutions retaintheir bitterness forseveral years evenwhenexposed to light.

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Denatonium benzoateis incompatible with strongoxidizing agents.

Regulatory Status

Denatonium benzoate is used worldwide as a denaturant for alcohol. It is included in the FDA Inactive Ingredients Database (topical gel and solution).

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