Denatonium benzoate
[CAS# 3734-33-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: Denatonium benzoate
• Synonyms: N-[2-[(2,6-Dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-benzenemethanaminium benzoate; N,N-Diethyl-N-[(2,6-dimethylphenylcarbamoyl)methyl]benzylammonium benzoate; Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate
• Molecular Formula: C₂₁H₂₉N₂O.C₇H₅O₂;C₂₈H₃₄N₂O₃
• Molecular Weight: 446.59
• CAS Registry Number: 3734-33-6
• EC Number: 223-095-2
• SMILES: CC[N+](CC)(CC1=CC=CC=C1)CC(=O)NC2=C(C=CC=C2C)C.C1=CC=C(C=C1)C(=O)[O-]

Properties

• Solubility: 10 mM (DMSO)
• Melting point: 164-168 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302+H332-H302-H318-H332-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P304+P340-P305+P354+P338-P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	2	H330
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H331
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

Denatonium benzoate, often recognized for its intensely bitter taste, is a chemical compound that serves as a potent bittering agent in various applications. The compound, also known as denatonium benzoate, was first synthesized in the mid-20th century as part of research into effective deterrents for ingesting toxic substances.

The discovery of denatonium benzoate can be traced back to efforts to develop a compound that would make harmful substances unpalatable. Its bitter taste is so extreme that it is often used in very small concentrations to ensure that its presence is detectable even in trace amounts. This quality has made it an invaluable tool in preventing accidental poisoning and misuse of potentially dangerous products.

Denatonium benzoate is used primarily as a bittering agent in a wide range of products, including industrial solvents, household cleaners, and antifreeze. By adding denatonium benzoate to these substances, manufacturers can significantly reduce the risk of accidental ingestion, particularly by children and animals. The compound's presence serves as a deterrent, making the products extremely unpleasant to taste and thus discouraging ingestion.

In addition to its use in consumer products, denatonium benzoate is employed in the formulation of various personal care products. It is added to products such as nail-biting deterrents, where its bitterness helps to discourage the habit by providing an immediate unpleasant sensory experience. This application underscores denatonium benzoate's versatility and its effectiveness in addressing behavioral issues related to habits.

Another significant application of denatonium benzoate is in the field of pharmaceuticals and medical devices. It is sometimes used to ensure that medications and medical devices are not tampered with or misused. For example, in some cases, it is added to medications to deter accidental or intentional overdosing by making the medication taste extremely bitter. This use helps to enhance the safety and efficacy of pharmaceutical products.

The compound is also employed in industrial settings where its presence helps to identify and prevent accidental exposure to hazardous substances. By incorporating denatonium benzoate into industrial chemicals, manufacturers can help protect workers and reduce the likelihood of accidental ingestion or exposure to dangerous chemicals.

Research into denatonium benzoate continues to explore its potential applications and effectiveness in various fields. The compound's strong bitter taste and its ability to serve as a deterrent make it a valuable asset in many industries, from consumer products to pharmaceuticals and industrial chemicals.

In summary, denatonium benzoate is a highly effective bittering agent used to prevent accidental ingestion of hazardous substances. Its discovery and application have had a significant impact on safety across a range of industries, highlighting its importance in protecting human health and well-being.

References

2024. Bitter taste receptors as sensors of gut luminal contents. Nature reviews. Gastroenterology & hepatology, 21(12).
DOI: 10.1038/s41575-024-01005-z

2024. Effects of a bitter substance, denatonium benzoate, on pancreatic hormone secretion. American journal of physiology. Endocrinology and metabolism, 326(4).
DOI: 10.1152/ajpendo.00046.2024

2024. Bitter tastants relax the mouse gallbladder smooth muscle independent of signaling through tuft cells and bitter taste receptors. Scientific Reports, 14(1).
DOI: 10.1038/s41598-024-69287-6