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Denatonium benzoate is the bitterest known chemical, used to deter ingestion of harmful substances. Denatonium benzoate is added to products like antifreeze, pesticides, and cleaning fluids to prevent accidental poisoning.
Even at extremely low concentrations, it produces an intense bitter taste that discourages consumption.
Denatonium benzoate is generally considered safe and non-toxic in the small amounts used for aversion purposes.
CAS Number: 3734-33-6
EC Number: 223-095-2
IUPAC Name: N-Benzyl-2-(2,6-dimethylanilino)-N,N-diethyl-2-oxoethan-1-aminium benzoate
Chemical Formula: C28H34N2O3
Other names: 3734-33-6, Bitrex, Lidocaine benzyl benzoate, Aversion, Denatonium (benzoate), Anispray, THS-839, Benzoato de denatonio, Benzoate de denatonium, Denatonium benzoate anhydrous, Denatonii benzoas, Caswell No. 083BB, WIN 16568, Denatonii benzoas [INN-Latin], Lignocaine benzyl benzoate, UNII-M5BA6GAF1O, M5BA6GAF1O, EINECS 223-095-2, Benzoate de denatonium [INN-French], Benzoato de denatonio [INN-Spanish], Denatonium benzoate [USAN:INN:BAN], MFCD00031578, EPA Pesticide Chemical Code 009106, NSC 157658, DTXSID8034376, NSC-157658, ECX-95BY, Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate, Benzyldiethyl((2,6-xylylcarbamoyl)methyl)ammonium benzoate, 3734-33-6 (benzoate), DENATONIUM BENZOATE [MI], DTXCID6014376, DENATONIUM BENZOATE [INN], UNII-4YK5Z54AT2, DENATONIUM BENZOATE [WHO-DD], denatonium benzoate monohydrate, NSC157658, WIN-16568, Benzenemethanaminium,N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate, LIDOCAINE BENZYL BENZOATE HYDRATE, Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate, NCGC00017043-02, Ammonium, benzyldiethyl((2,6-xylylcarbamoyl)methyl)-, benzoate, CAS-3734-33-6, Gori, Bitrex (TN), Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate (1:1), Denatonii benzoas (INN-Latin), Denatonium benzoate (NF), Benzoate de denatonium (INN-French), Benzoato de denatonio (INN-Spanish), Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate, DENATONIUM BENZOATE (II), DENATONIUM BENZOATE [II], N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-N,N-DIETHYLBENZENEMETHANAMINIUM BENZOATE, N-benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzoate, DTXSID50235522, DENATONIUM BENZOATE [USAN], DENATONIUM BENZOATE [VANDF], DENATONIUM BENZOATE (MART.), DENATONIUM BENZOATE [MART.], DENATONIUM BENZOATE (USP-RS), DENATONIUM BENZOATE [USP-RS], Denatonium benzoate [USAN:INN:BAN:NF], Denatonium benzoate granules, Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate (1:1), N-Benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethanaminium benzoate, Benzoato di denatonio, ARBINOL B, BENZENEMETHANAMINIUM, N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-N,N-DIETHYL-, BENZOATE, HYDRATE (1:1:1), SCHEMBL49511, MLS002154073, Denatonium benzoate, >=98%, THS839, Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate, CHEMBL1371493, HY-B1146R, DTXCID80158013, Denatonium (benzoate) (Standard), ((2,6-Xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate, DENATONIUM BENZOATE [INCI], HMS1571A03, HMS2093L12, HMS2098A03, HMS2233O05, HMS3373C04, HMS3715A03, Pharmakon1600-01505987, HY-B1146, Tox21_110754, Tox21_301587, benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium;benzoate, NSC759299, AKOS015888129, N,N-Diethyl-N-[(2,6-dimethylphenylcarbamoyl)methyl]benzylammonium benzoate, Tox21_110754_1, CCG-213592, CS-4750, FD53581, NSC-759299, Denatonium benzoate, analytical standard, N-(2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme- thanaminium benzoate, NCGC00017043-01, NCGC00091886-04, NCGC00164432-01, NCGC00255373-01, AC-14888, AC-37592, AS-15511, SMR001233385, SY075333, DB-049095, Ammonium,6-xylylcarbamoyl)methyl]-, benzoate, D2124, F16467, Q414815, Benzyldiethyl((2,6xylylcarbamoyl)methyl)ammonium benzoate, ((2,6Xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate, Ammonium, benzyldiethyl((2,6xylylcarbamoyl)methyl), benzoate, Denatonium benzoate, certified reference material, TraceCERT(R), Benzyldiethyl[(2,6-dimethylphenylcarbamoyl)methyl]ammonium Benzoate, Benzyl-[(2,6-dimethylphenylcarbamoyl)-methyl]diethylammonium benzoate, Benzyl-[(2,6-dimethylphenylcarbamoyl)methyl]-diethylammonium benzoate, Denatonium benzoate, United States Pharmacopeia (USP) Reference Standard, Benzenemethanaminium, N(2((2,6dimethylphenyl)amino)2oxoethyl)N,Ndiethyl, benzoate, Benzenemethanaminium,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate, N(2((2,6Dimethylphenyl)amino)2oxoethyl)N,Ndiethylbenzenemethanaminium benzoate, N-(2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme-thanaminium benzoate
Bitterants such as denatonium benzoate are useful as aversive additives to prevent accidental ingestion of hazardous automotive compounds. In Europe and in some U.S. states, addition of denatonium benzoate is required in ethylene glycol or anti-freeze and windshield washer fluids. Common household products such as window cleaners, disinfectants, laundry detergent and insecticide include a certain amount of denatonium benzoate to discourage consumption by mouth.
Denatonium benzoate is applied on surfaces of toys as a bittering agent to prevent substantial consumption of hazardous materials. Denatonium benzoate is also applied on outdoor cables and wires to discourage rodents from chewing on parts and equipment. Denatonium benzoate is an aversive agent added to various pesticides, plant food sticks and rodenticides to suppress swallowing especially when young children come in contact with these poisonous substances.
By far, the most common use of denatonium benzoate is to denature alcohol, making Denatonium benzoate unfit for human consumption and exempt from tariffs that normally apply to alcohol.In livestock farming, denatonium benzoate is used to prevent cannibalism in pigs and aspiration mastitis in cattle. Denatonium benzoate acts as a repellant when applied to young shoots, branches and other surfaces to discourage nibbling by animals, thereby preventing damage to property.
Denatonium benzoate has a chemical weight of 446.58116 g/mol and a molecular formula of C28 H3 4N 2O3.
Denatonium benzoate is a compound of salt with an inert anion such as benzoate or saccharide.
Denatonium benzoate's structure is similar to lidocaine and is closely related to Novocain and benzocaine. Denatonium benzoate is odorless, colorless and non-reactive, making Denatonium benzoate a suitable additive that does not interfere with the primary purpose of the base compound.
Denatonium benzoate acts as a repellant when applied to young shoots, branches and other surfaces to discourage nibbling by animals, thereby preventing damage to property. Keep away from heat. Keep away from sources of ignition. Empty containers pose a fire risk, evaporate the residue under a fume hood. Ground all equipment containing material. Do not ingest.
Do not breathe dust. Avoid contact with eyes Wear p. 3 suitable protective clothing In case of insufficient ventilation, wear suitable respiratory equipment If ingested, seek medical advice immediately and show the container or the label.Keep container dry. Keep in a cool place. Ground all equipment containing material. Keep container tightly closed. Keep in a cool, well-ventilated place. Combustible materials should be stored away from extreme heat and away from strong oxidizing agents.Very hazardous in case of ingestion. Hazardous in case of inhalation.
Slightly hazardous in case of skin contact (irritant).Denatonium, usually available as denatonium benzoate (under trade names such as Denatrol, BITTERANT-b, BITTER+PLUS, Bitrex or Aversion) and as denatonium saccharide (BITTERANT-s), is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide. Denatonium benzoate was discovered in 1958 during research on local anesthetics by MacFarlan Smith of Edinburgh, Scotland, and registered under the trademark Bitrex. Dilutions of as little as 10 ppm are unbearably bitter to most humans.
Denatonium salts are usually colorless and odorless solids but are often traded as solutions. They are used as aversive agents (bitterants) to prevent inappropriate ingestion. Denatonium is used in denatured alcohol, antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps, and shampoos. Denatonium benzoate is not known to pose any long-term health risks.
Although denatonium benzoate has a powerful taste, Denatonium benzoate is colorless and odorless. The taste is so strong, however, that most people cannot tolerate a concentration of more than 30 parts per million of denatonium benzoate. Solutions of denatonium benzoate in alcohol or water are very stable and retain their bitter taste for many years.
Exposure to light does not lessen the compound's bitter taste. Denatonium benzoate has been used in the United States for over 20 years as an alcohol denaturant. In recent years, Denatonium benzoate has been heavily promoted for inclusion in household products, gardening products, and cosmetics to prevent accidental ingestions by children. A concentrated solution of denatonium benzoate which would be sold directly to the public for addition to household products is available in USA.
The efficacy and safety studies on denatonium benzoate are limited and may be subject to varying interpretations when viewed in the context of a potential poisoning situation. Safety data indicate a low toxicity profile. However, there are significant gaps in knowledge, especially relating to chronic toxicity in humans, teratogenicity, and human hypersensitivity potential.
A 33-year-old man developed asthma and urticaria from exposure to denatonium benzoate in an insecticidal spray. He had previously developed the same symptoms following exposure to an alcohol-based skin disinfectant and other products denatured with denatonium benzoate. The cause of his symptoms was thus likely to be an immunologic mechanism of the immediate hypersensitivity-type.
And that’s so much more useful than a dose of kryptonite. Denatonium benzoate (3734-33-6) has been investigated for Carcinogenicity to a greater or lesser extent. Often the studies based on in vivo experiments in rodents, i.e. most commonly in rats Denatonium benzoate (3734-33-6) In experimental study given by Cosmetic Ingredient Review Expert Panel (International Journal of Toxicology, 27(Suppl. 1):1–43, 2008) In a Chronic toxicity study, Denatonium benzoate, dissolved in distilled water, was administered by gavage at dosage levels of 1.6, 8 or 16 mg/kg/day with a total administration volume of 10 ml/kg/day. The rats were observed for overt signs of toxicity, mortality, body weight, food consumption and efficiency.
Ophthalmoscopic, haematological, biochemistry, urine analysis, gross and histopathological examinations were also investigated. No mortalities occurred that could be directly attributed to treatment. Similarly, no changes were observed in body weight, food consumption, food efficiency, opthalmoscopic, hematology or clinical chemistry.
In addition, no change were observed in organ weight, gross pathology and histopathology of treated male and female rat when compared with control. Some changes were observed on terminal sacrifice but the effect is not regarded to be substance-related. Since no alterations were observed in the test groups from the control groups the effects observed were not considered to be compound related. The tumors observed were not regarded to be the result of a tumorigenic effect of the test material.
Despite the fact that no statistical calculations could be performed due to the low numbers of animals tested, and since no compound related effects were observed, the results still indicates towards a No Observed Adverse Effect Level (NOAEL) (relating systemic chronic effects and carcinogenicity) of 16 mg/kg per day for the given test chemical.
Thus, comparing this value with the criteria of CLP regulation, Denatonium benzoate (3734-33-6) can be not classified for Carcinogenicity in rats by oral route exposed for 2 years. Denatonium, usually available as denatonium benzoate (trade names Bitrex) is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide. Scientists at Macfarlan Smith, Ltd. of Edinburgh, Scotland discovered Bitrex during research on derivatives of the anesthetic lidocaine.
The extremely bitter taste proved effective in reducing ingestion by humans and animals. Denatonium is commonly included in placebo medications used in clinical trials to match the bitter taste of certain medications. Denatonium activates bitter taste receptor, mainly, TAS2R4, TAS2R8, TAS2R10, TAS2R13 on many cell types and plays important roles in chemical release, ciliary beating and smooth muscle relaxation through intracellular Ca(2+)-dependent pathways. Denatonium inhibits growth and induces apoptosis of airway epithelial cells. After treatment with 2 mM denatonium for 24 h, the expression of the anti-apoptotic protein Bcl-2 was significantly reduced and the release of cytochrome c and Smac/DIABLO from the mitochondria to the cytoplasm was drastically increased in human bronchial epithelial cell lines 16HBE.
To examine whether denatonium induces mitochondrial damage in airway epithelial cells, was used transmission electron microscopy to examine the ultrastructures of human lung cancer cell line A549 treated with 2 mM denatonium. The control cells appeared to have normal mitochondria and mostly homogeneous cytoplasms, while A549 cells treated with denatonium showed large amplitude swelling of mitochondria.
Illegal alcoholic beverages are often introduced into market using cheap technical alcohol, which is contaminated by denatonium benzoate (Bitrex) of very small concentration. Bitrex is the most bitter chemical compound and has to be removed before alcohol consumption. The home‐made methods utilize sodium hypochlorite to disintegrate particles of denatonium benzoate in alcohol and to remove bitter taste before trading.
In this experimental studies, we propose a novel method that detects in a fast way the remnants of denatonium benzoate in dubious alcohol samples by Raman spectroscopy. Denatonium Benzoate, t-Butyl Alcohol, Diethyl Phthalate, Methyl Alcohol, Salicylic Acid, Sodium Salicylate, and Methyl Salicylate are examples of denaturants permitted for use by the TTB and concluded to be safe for use in cosmetics. Other countries have different rules on allowed denaturants so when formulating you should check with local regulations.
Specific denatured alcohols containing these denaturants that are permitted for use in U.S. cosmetics and personal care products are SD Alcohol 3-A, SD Alcohol 30, SD Alcohol 39-B, SD Alcohol 39-C, SD Alcohol 40-B and SD Alcohol 40-C. Denatonium benzoate is one of the most bitter substances known. Just a few parts per million will make a product so bitter that children and pets will not be able to swallow Denatonium benzoate.
Denatonium benzoate makes sweet but highly toxic products such as antifreeze and detergents taste foul. Research shows that people can detect denatonium benzoate in water at 50 parts per billion. Denatonium benzoate is bitter at 1 to 10 ppm and most products will become undrinkable at 30 to 100 ppm. Denatonium benzoate is also stable and inert. In addition, so little is needed that the properties of the product remain unchanged Denatonium benzoate is a compound of salt with an inert anion such as benzoate or saccharide.
Its structure is similar to lidocaine and is closely related to Novocain and benzocaine. Denatonium benzoate is odorless, colorless and non-reactive, making Denatonium benzoate a suitable additive that does not interfere with the primary purpose of the base compound.Humans can typically sense sweet, sour, salty, savory and bitter-tasting stuff. Of these flavors, bitter-tasting chemicals elicit the most reaction. Sensitivity to bitter flavors depends on genetics: The TAS2R38 gene determines a person’s ability to detect the bitterness associated with substances such as quinine, which is an ingredient in tonic water.
Denatonium benzoate is also the standard for this type of bitter flavor. At a concentration of 0.008 moles per cubic meter, the human tongue can detect the presence of quinine. For denatonium benzoate, a concentration of 0.000008 moles per cubic meter is discernible to humans. Bitterants such as denatonium benzoate are useful as aversive additives to prevent accidental ingestion of hazardous automotive compounds.
Denatonium, usually available as denatonium benzoate (under trade names such as Denatrol, BITTERANT-b, BITTER+PLUS, Bitrex or Aversion) and as denatonium saccharide (BITTERANT-s), is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide. Denatonium benzoate was discovered in 1958 during research on local anesthetics by MacFarlan Smith of Edinburgh, Scotland, and registered under the trademark Bitrex.
Dilutions of as little as 10 ppm are unbearably bitter to most humans. Denatonium salts are usually colorless and odorless solids but are often traded as solutions. They are used as aversive agents (bitterants) to prevent inappropriate ingestion. Denatonium is used in denatured alcohol,antifreeze, preventive nail biting preparations, respirator mask fit-testing, animal repellents, liquid soaps, shampoos, and even Nintendo Switch game cards to prevent accidental swallowing or choking by children.
Denatonium benzoate is not known to pose any long-term health risks. Denatonium is a quaternary ammonium cation. Denatonium benzoate is a compound of a salt with an inert anion like benzoate or saccharide. The structure of denatonium is related to the local anesthetic lidocaine, differing only by the addition of a benzyl group to the amino nitrogen. Other similar compounds are procaine and benzocaine.
One of the chemical names for the compound is lidocaine benzylbenzoate, although denatonium only denotes the quaternary ammonium cation species itself, and does not necessitate the benzoate counterion. Denatonium also discourages consumption of harmful alcohols like methanol, and additives like ethylene glycol.
Denatonium is used in rubbing alcohol as an inactive ingredient. It is also added to many kinds of harmful liquids including solvents (such as nail polish remover), paints, varnishes, toiletries and other personal care items, special nail polish for preventing nail biting, and various other household products.
Denatonium benzoate is also added to less hazardous aerosol products (such as gas dusters) to discourage inhalant abuse of the volatile vapors.
Denatonium benzoate is a compound of salt with an inert anion such as benzoate or saccharide.
Denatonium benzoate's structure is similar to lidocaine and is closely related to Novocain and benzocaine.
Denatonium benzoate is odorless, colorless and non-reactive, making Denatonium benzoate a suitable additive that does not interfere with the primary purpose of the base compound.
Humans can typically sense sweet, sour, salty, savory and bitter-tasting stuff.
