Denatonium Benzoate

Chemical properties

white crystals

Chemical properties

Denatonium benzoate occurs as an odorless, very bitter tasting, white crystalline powder or granules.

The Uses of Denatonium Benzoate

The bitterest compound knownDenatonium benzoate is used as an alcohol denaturant and flavour in pharmaceuticals. It is also used in antifreeze, nail-biting preventions, respirator mask fit-testing, animal repellents, liquid soaps and shampoos. Further, it is used in air care products. It acts as H1 antihistamine. In addition to this, it is used as a disinfectant. It can replace brucine or quassin as a denaturant for ethyl alcohol.

Production Methods

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

brand name

Bitrex (Mac Farlan Smith, Scotland).

Pharmaceutical Applications

Denatonium benzoate is among the most bitter 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 replace brucine or quassin as a denaturant for ethanol. In pharmaceutical formulations, denatonium benzoate has been used as a flavouring 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 specific 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 Denatonium Benzoate.

Description

Denatonium benzoate (Bitrex?) has been used in the United States for over 20 years as an alcohol denaturant. In recent years, it has been heavily promoted for inclusion in household products, gardening products, and cosmetics to prevent accidental ingestions by children. Denatonium benzoate (DB), one of the most bitter-tasting substances known, is described as highly unpleasant at a lower amount and can cause perceptible bitterness. DB has been demonstrated extensively as a bitter taste agonist and used to activate bitter taste receptors in many cell types, including taste cells. DB is intensely bitter and non-toxic and can be detected by human taste receptors. For these reasons, DB has been broadly added to liquid detergents, cosmetics, plastic toys and personal care products to avoid the consumption of harmful substances. Aside from its strong bitter taste, DB also exerts biological effects on various physiological systems in different organisms. Exposure to DB quickly suppressed ongoing intake and delayed gastric emptying in rodents.

storage

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.

Incompatibilities

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).