Denatonium Benzoate Chemical Properties

Melting point:

164-168 °C (lit.)

Boiling point:

555.91°C (rough estimate)

Density 

1.1256 (rough estimate)

vapor pressure 

0Pa at 25℃

refractive index 

1.5800 (estimate)

Flash point:

100℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

methanol: 50 mg/mL, clear, colorless

form 

Solid

color 

White to Off-White

Odor

at 100.00?%. bland

Water Solubility 

42.555g/L at 25℃

Merck 

14,2891

BRN 

8179408

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

VWTINHYPRWEBQY-UHFFFAOYSA-N

LogP

2.2 at 25℃

CAS DataBase Reference

3734-33-6(CAS DataBase Reference)

EPA Substance Registry System

Denatonium benzoate (3734-33-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-37/39

WGK Germany 

2

RTECS 

BO6650000

TSCA 

Yes

HS Code 

29242995

MSDS

• Language:English Provider:Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate
• Language:English Provider:SigmaAldrich

Denatonium Benzoate Usage And Synthesis

The most bitter compound in the world

Denatonium benzoate is now known as the world's most bitter compound. If we set the bitter degree of quinine as datum 1, the degree of bitterness of the product would be 1000. A concentration of 10ppm solution is already too bitter to bear for most people. The vast majority of its applications are related to its bitter flavor. It is an inexpensive and efficient alternative to its counterparts such as strychnine, bitter lignin, quinine, wood song glycosides, saponins grapefruit.
Denatonium benzoate is commonly used as aversive agent to prevent people from eating other toxic but tasteless substance. For example, it has been added into industrial alcohol, ethylene glycol or methanol which has similar taste as ordinary wine, antifreeze, paint, toilet cleaners, animals disperse, liquid soaps and shampoos. Moreover, it has been also added into special nail polish agents, to avoid child’s bad habit of biting fingers, as well as being the repellent for expulsing large beasts. However, the effect of Long-term exposure to this substance on human health is still unclear.

Chemical structure

Denatonium benzoate is a kind of quaternary ammonium salt formed by the combination of the quaternary ammonium cation and inert anion such as benzoic acid or saccharin anion. The structure of its cation form is similar to that of a local anesthetic lidocaine with the only difference being an additional benzyl functional group located on the nitrogen atom of the amino.

Uses

Flavoring agent.

Chemical Properties

white crystals

Chemical Properties

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

Uses

The bitterest compound knownDenatonium benzoate is used as an alcohol denaturant and flavor 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.

Uses

Pharmaceutic aid (alcohol denaturant; flavor). Added to toxic substances as a deterrent to accidental ingestion. Can replace brucine or quassin as 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).

Flammability and Explosibility

Not classified

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.

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).

Denatonium Benzoate(3734-33-6)Related Product Information

• Benzyltrimethylammonium chloride
• Benzyltriethylammonium chloride
• Ammonium chloride
• Ammonium benzoate
• Ammonium sulfate
• 4-Aminobenzoic acid
• Glycyrrhizic acid ammonium salt
• Cisatracurium besylate
• Diethyl malonate
• ALTRENOGEST
• Benzyl chloride
• Benzyl benzoate
• Benzoic acid
• Benzyl bromide
• Benzyldodecyldimethylammonium bromide
• Glycine
• 4-Nitrobenzoic acid
• Molybdic acid