DENATONIUM BENZOATE
Denatonium benzoate is recognized as the world's most bitter chemical compound, commonly used to deter accidental ingestion by making products extremely unpalatable.
Denatonium benzoate renders a product undrinkable at concentrations as low as a few parts per million, making it an effective deterrent in a wide range of industrial and consumer products.
Discovered in 1958 by T.& H. Smith in Edinburgh, Scotland, Denatonium benzoate is now widely used in various products such as cleaning agents, antifreeze, and personal care items to prevent ingestion.
CAS Number: 3734-33-6
EC Number: 223-095-2
Molecular Formula: C28H34N2O3
Molecular Weight: 446.58a
Synonyms: Bitrex, Bitrex (Denatonium Benzoate), 3734-33-6, Lidocaine benzyl benzoate, THS-839, Denatonium (benzoate), Aversion, Bitrex (Denatonium Benzoate) anhydrous, Benzoato de denatonio, Benzoate de denatonium, Lignocaine benzyl benzoate, WIN 16568, MFCD00031578, M5BA6GAF1O, NSC-157658, ECX-95BY, Benzyldiethyl((2,6-xylylcarbamoyl)methyl)ammonium benzoate, 3734-33-6 (benzoate), DTXSID8034376, NSC 157658, WIN-16568, Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate, Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate, NCGC00017043-02, Anispray, CAS-3734-33-6, Gori, DTXCID6014376, Caswell No. 083BB, Denatonii benzoas, N-benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzoate, Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate (1:1), Denatonii benzoas [INN-Latin], LIDOCAINE BENZYL BENZOATE HYDRATE, EINECS 223-095-2, UNII-M5BA6GAF1O, Benzoate de denatonium [INN-French], Benzoato de denatonio [INN-Spanish], Bitrex (Denatonium Benzoate) [USAN:INN:BAN], EPA Pesticide Chemical Code 009106, N-Benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethanaminium benzoate, Benzoato di denatonio, SCHEMBL49511, MLS002154073, Bitrex (Denatonium Benzoate), >=98%, Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate, CHEMBL1371493, Bitrex (Denatonium Benzoate) [MI], Bitrex (Denatonium Benzoate) [INN], VWTINHYPRWEBQY-UHFFFAOYSA-N, ((2,6-Xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate, Bitrex (Denatonium Benzoate) [INCI], HMS1571A03, HMS2093L12, HMS2098A03, HMS2233O05, HMS3373C04, HMS3715A03, Pharmakon1600-01505987, Ammonium, benzyldiethyl((2,6-xylylcarbamoyl)methyl)-, benzoate, HY-B1146, Tox21_110754, Tox21_301587, benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium;benzoate, Bitrex (Denatonium Benzoate) [WHO-DD], NSC157658, NSC759299, AKOS015888129, benzyl-[2-(2,6-dimethylanilino)-2-oxo-ethyl]-diethyl-ammonium benzoate, N,N-Diethyl-N-[(2,6-dimethylphenylcarbamoyl)methyl]benzylammonium benzoate, Tox21_110754_1, CCG-213592, CS-4750, NSC-759299, Bitrex (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, AS-15511, SMR001233385, SY075333, Ammonium,6-xylylcarbamoyl)methyl]-, benzoate, D2124, FT-0622841, F16467, A823606, Q414815, W-106547, Bitrex (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, Bitrex (Denatonium Benzoate), United States Pharmacopeia (USP) Reference Standard, Benzenemethanaminium,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate, Benzenemethanaminium,N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate, N-benzyl-2-(2,6-dimethylphenylamino)-N,N-diethyl-2-oxoethanaminium benzoate, N-(2-((2,6-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)-N,N-DIETHYLBENZENEMETHANAMINIUM BENZOATE
Denatonium benzoate is available as a white crystalline powder, but Denatonium benzoate granules or solutions are also available.
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.
Denatonium benzoate is a bittering agent.
Denatonium benzoate is used as an alcohol denaturant and flavor in pharmaceuticals.
Denatonium benzoate is considered the bitterest chemical compound with a range of uses in the manufacture of cleaners, automotive supplies as well as health and beauty items.
Denatonium benzoate was discovered in 1958 during research on local anesthetics by T.& H. Smith of Edinburgh, Scotland, and registered under the trademark Denatonium benzoate.
Additionally, Denatonium benzoate is used in products like soap, animal repellents, antifreeze.
The structure of Denatonium benzoates 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.
Denatonium benzoate, often referred to as Denatonium benzoate, is a chemical compound primarily used as a bittering agent.
Denatonium benzoate is commonly added to a wide range of products to make them unpalatable, thereby discouraging ingestion or consumption, especially by children, pets, or individuals seeking to misuse these products.
Denatonium benzoate is now known as the world's most bitter compound.
A concentration of 10ppm solution is already too bitter to bear for most people.
Denatonium benzoate is known for being one of the most bitter substances known to humans.
Denatonium benzoate is an ionized compound made up of a negatively charged benzoic acid and quaternary ammonium cation.
The vast majority of its applications are related to its bitter flavor.
Denatonium benzoate is an inexpensive and efficient alternative to its counterparts such as strychnine, bitter lignin, quinine, wood song glycosides, saponins grapefruit.
Dilutions of as little as 10 ppm are unbearably bitter to most humans.
Denatonium benzoate 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 benzoate is used in denatured alcohol, antifreeze, preventive nail biting preparations, respirator mask fit-testing, animal repellents, liquid soaps, shampoos, and 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 benzoate reflects the substance's primary use as a denaturant and its chemical nature as a cation, hence -onium as a Neo-Latin suffix.
Denatonium benzoate is commonly used as aversive agent to prevent people from eating other toxic but tasteless substance.
Denatonium benzoate 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.
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 Denatonium benzoate is added to some products as a deterrent to accidental ingestion.
Denatonium benzoate 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.
Denatonium benzoate 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.
Denatonium benzoate 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 Denatonium benzoate on human health is still unclear.
Denatonium benzoate is a white, odorless, and mostly tasteless crystalline powder.
In pharmaceutical formulations, Denatonium benzoate has been used as a flavoring agent in placebo tablets, and in a topical formulation Denatonium benzoate has been used in an anti-nailbiting preparation.
Denatonium benzoate is added to various household products like cleaning agents, detergents, and solvents to deter accidental ingestion.
In pharmaceutical and other industrial applications it is added to some products as a deterrent to accidental ingestion.
Denatonium benzoate 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 antinailbiting preparation.
Denatonium benzoate is generally regarded as a nonirritant and nonmutagenic substance.
However,there has been a single report of 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.
Discovered in 1958, it also has the tradename "Denatonium benzoate" (a trademark of UK company Macfarlan Smith).
As little as ten parts per million make substances unbearably bitter to most humans.
Denatonium benzoate is a white, odourless solid that is used as an aversive agent, i.e. an additive that prevents accidental ingestion of a toxic substance by humans, articularly children, and by animals.
Denatonium benzoate consists of benzoate (that is, the conjugate base of benzoic acid) and an ester of two PABA molecules.
Its structure is related to lidocaine, differing only by the addition of a benzene and benzoate ion in solution.
Denatonium benzoate does, however, cause a very bitter taste in humans and most animals at concentrations in the parts per million range.
Denatonium benzoate is a quaternary ammonium cation.
Denatonium benzoate is composed as a salt with any of several anions, such as benzoate or saccharinate.
Denatonium benzoate can be obtained by the quaternization of lidocaine, a popular anesthetic, with benzyl chloride or a similar reagent.
To obtain other salts, like the benzoate, the formed denatonium chloride is subjected to an anion exchange reaction with sodium benzoate, or first sodium hydroxide to make denatonium hydroxide followed by neutralization with benzoic acid.
Other similar compounds are procaine and benzocaine.
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's also similar in structure to other anesthetics like novocaine and cocaine.
Indeed, Denatonium benzoate was discovered during anesthetic research.
Denatonium benzoate, a white crystalline powder like many organic compounds, is not known to pose any long-term health risks although exposure may be irritating.
Some automotive products, such as antifreeze and windshield washer fluids, contain Denatonium benzoate to prevent accidental ingestion, which could be harmful.
Certain paints and coatings may include Denatonium benzoate to discourage consumption, which could be toxic.
Nail polish removers may contain Denatonium benzoate to make them taste bad, preventing ingestion.
Some personal care products, like nail polish, perfumes, and cosmetics, use Denatonium benzoate to make them unappealing to taste.
In some cases, Denatonium benzoate is used in medications to deter misuse or accidental ingestion.
Denatonium benzoate can act as a bronchodilator by activating bitter taste receptors in the airway smooth muscle.
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.
Denatonium benzoate is a rather more convenient name than phenylmethyl-[2- [(2,6-dimethylphenyl)amino]-2-oxoethyl]-diethylammonium.
Denatonium benzoate is a quaternary ammonium cation, with two ethyl arms, one benzyl and one larger amide one, and usually comes as a benzoate - a salt of benzoic acid.
Denatonium benzoates claim to fame is simple, unpleasant but valuable - Denatonium benzoate is the most bitter substance yet discovered.
The bitterest compound known Denatonium benzoate is used as an alcohol denaturant and flavor in pharmaceuticals.
The process adds a small amount of a denaturant to the alcohol to make it taste bad, thus creating alcohol that is not suitable for drinking, but is otherwise similar for other purposes.
When used in products that are not food, beverages or oral drugs, many other countries, like the U.S., also require that alcohol be denatured.
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 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 the most bitter chemical compound known,used as aversive agents (bitterants) to prevent inappropriate ingestion.
Denatonium benzoate is used in denatured alcohol, antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps, and shampoos.
Denatonium benzoate, is the bitterest known chemical compound with bitterness thresholds of 0.05 ppm for benzoate and 0.01 ppm for saccharide.
Scientists in Scotland discovered Denatonium benzoate during research on anesthetic lidocaine derivatives.
Denatonium benzoate’s extremely bitter taste has proven effective in reducing ingestion by humans and animals.
Denatonium benzoate is often included in placebo drugs used in clinical trials to match the bitter taste of certain drugs.
Denatonium benzoate activates bitter taste receptors in many cell types and plays important roles in chemical release, ciliary beating and smooth muscle relaxation through intracellular dependent pathways.
Denatonium benzoate is one of the bitterest known substances.
Just a few parts per million make a product so painful that kids and pets can't swallow Denatonium benzoate.
Sweet but highly toxic products such as Denatonium benzoate, antifreeze and detergents make their taste bad.
Studies show that humans can detect 50 parts per billion of Denatonium benzoate in water.
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.
Denatonium benzoate is also used in antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps and shampoos.
Further, Denatonium benzoate is used in air care products.
Denatonium benzoate acts as H1 antihistamine.
In addition to this, Denatonium benzoate is used as a disinfectant.
In order to avoid paying beverage taxes on alcohol that is not meant to be consumed (e.g., for use in cosmetic and personal care products), the alcohol must be denatured per specific formulations given by the U.S.
Denatonium benzoate is among the most bitter of substances known and is detectable at concentrations of approximately 10 ppb.
Denatonium benzoate, also called Benzenemethanaminium and Benzyl diethyl ((2,6-xylylcarbamoyl)methyl) ammonium benzoate, is the bitterest compound known.
In addition, little is needed for the properties of the product to remain unchanged.
Often found as Denatonium benzoate and denatonium saccharide, Denatonium benzoate is the bitterest known chemical compound, with bitter thresholds being 0.05. ppm for benzoate and 0.01 ppm for saccharide.
Denatonium benzoate was discovered in 1958 during research on local anesthetics by MacFarlan Smith of Edinburgh, Scotland, and registered under the Denatonium benzoate trademark.
Dilutions as little as 10 ppm are unbearably bitter for most people.
Denatonium benzoate is chemical structure includes a benzoate group, which is a benzene ring attached to a carboxylic acid group, along with a denatonium cation.
The Denatonium benzoate cation is the component responsible for its intensely bitter taste.
Denatonium benzoate is considered one of the most bitter substances known to humans.
Denatonium benzoate is often used as a reference point for measuring bitterness.
The bitter taste is so extreme that even in minute quantities, Denatonium benzoate can make a product unpalatable.
Denatonium benzoate is generally considered safe when used as intended in the recommended concentrations.
Denatonium benzoate is non-toxic and is not absorbed significantly through the skin, making it safe for use in a wide range of consumer products.
The use of Denatonium benzoate is subject to regulations in many countries.
There may be restrictions on its use in certain products, and there are guidelines on the maximum allowable concentration in specific applications.
Denatonium benzoate is not known to pose any long-term health risks.
The name Denatonium benzoate is a portmanteau word that reflects the primary use of the substance as a denaturant and Denatonium benzoate’s chemical structure as a cation, hence the New Latin suffix -onium.
Denatonium benzoate is a quaternary ammonium cation.
Denatonium benzoate is a salt compound with an inert anion such as benzoate or saccharide.
The structure of Denatonium benzoate is related to the local anesthetic lidocaine, which differs only by the addition of a benzyl group to amino nitrogen.
Other similar compounds are procaine and benzocaine.
One of the chemical names of Denatonium benzoate is lidocaine benzylbenzoate, but denatonium only refers to the quaternary ammonium cation species itself and does not require benzoate counterion.
The bitterness of the compound guides most of the Denatonium benzoate applications.
Denatonium benzoate is used to denature ethanol so that Denatonium benzoate is not treated as an alcoholic beverage in terms of taxation and sales restrictions.
A particular designation states that ethanol has been denatured using Denatonium benzoate.
Denatonium benzoate is often included in placebo drugs used in clinical trials to mimic the bitter taste of some drugs.
Denatonium benzoate also discourages the consumption of harmful alcohols such as methanol and additives such as ethylene glycol.
Denatonium benzoate is also added to many harmful liquids, including solvents (such as nail polish remover), paints, polishes, toiletries and other personal care products, special nail polish to prevent nail biting, and various other household products.
Denatonium benzoate is also added to less hazardous aerosol products (such as gas jets) to avoid inhaled substance abuse of volatile vapors.
In 1995, the US state of Oregon required the addition of Denatonium benzoate to products such as antifreeze and windshield washer fluid containing sweet-tasting ethylene glycol and methanol to prevent.
Denatonium benzoate's disgusting taste can be used as a deterrent on products that are not intended for consumption and / or is harmful upon consumption.
Nintendo Switch game cards are coated with Denatonium benzoate to prevent young children from consuming them.
Denatonium benzoate is used as a solvent in the food and beverage industry and in many home and personal care products.
Denatonium benzoate is often used in marketing and labeling to indicate that a product contains Denatonium benzoate as a bittering agent.
Apart from the previously mentioned applications, Denatonium benzoate is used in various other products, such as denatured alcohol (to deter its consumption), some types of pesticides (to prevent oral ingestion), and even in some nail polishes to discourage nail-biting.
In some therapeutic contexts, Denatonium benzoate is used in taste aversion therapy.
This involves pairing the bitter taste of Denatonium benzoate with a specific behavior (e.g., smoking or nail-biting) to create a psychological aversion to that behavior.
Denatonium benzoate, commonly found as Denatonium and Denatonium Saccharide, is the bitterest known chemical compound with bitter thresholds of 0.05 ppm for benzoate and 0.01 ppm for saccharide.
They are used as deterrents (bitterness) to prevent chemical and dangerous products from being swallowed improperly.
Denatonium benzoate is used in denatured alcohol, antifreeze, breathing mask compatibility test, repellents, liquid soaps and shampoos.
Denatonium benzoate is generally regarded as having the most bitter taste of any compound known to science.
Denatonium benzoate is sold under the trade name of Denatonium benzoate.
Although Denatonium benzoate has a powerful taste, it 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 is a bitter chemical compound used to denature ethanol so it is not considered an alcoholic beverage and in clinical trials to replicate the bitter taste of some medications.
Ungraded products supplied by TCI America are generally suitable for common industrial uses or for research purposes but typically are not suitable for human consumption or therapeutic use.
Denatonium benzoate (Denatrol) is a bittering agent used as an aversion additive in various chemical and manufactured products.
Connect Chemicals is the appointed distributor of the Denatonium benzoate product range of Wincom is a leading manufacturer of Denatonium benzoate located in the United States.
The primary use of Denatonium benzoate is for taste a version purposes for poison prevention.
Denatonium benzoate not only leaves a bitter flavor in the liquids, but also leaves a bitter residue on objects, like screens and keyboards, that may transfer to hands and cause problems (such as when eating).
Denatonium benzoate is not intended for use in any products or chemicals in which the intention is human ingestion.
Denatonium benzoate is a white powder with a water solubility of 42 grams per liter.
One gram of Denatonium benzoate can produce an extremely bitter and unpleasant taste in 100 liters of water (30 gallons).
Denatonium benzoate is so bitter that humans and pets can't stand it. Denatonium benzoate is the active ingredient in products such as Tree Guard and Denatonium benzoate.
Denatonium benzoate is also used in combination with bad smelling compounds to repel animals.
Denatonium benzoate is the active ingredient in products such as "Off Limits Dog Training Spray", "Anit-Chew Bitter Spray for Pets", "Ultra-Bitter Training Aid Spray", and "Bitter YUCK! No Chew Dog, Cat & Horse Spray".
Some examples of products which contain Denatonium benzoate are antifreeze, detergents (in ethanol), floor cleaner, paint stripper and toilet cleaner.
Denatonium benzoate salts are usually colorless and odorless solids, but are often sold as solutions.
They are used as deterrent agents (bitterness) to prevent inappropriate ingestion.
Denatonium benzoate is used in denatured alcohol, antifreeze, preventative nail biting preparations, respiratory mask compatibility tests, animal repellents, liquid soaps, shampoos, and even Nintendo Switch playing cards to prevent children from accidentally swallowing or suffocating.
Denatonium benzoate’ s bitter properties make Denatonium benzoate an excellent repellent and when added to phytosanitary products it contributes to inhibiting the feeding of animals on treated trees and plants.
Denatonium benzoate is a rather more convenient name than phenylmethyl-[2- [(2,6-dimethylphenyl)amino]-2-oxoethyl]-diethylammonium.
Denatonium benzoate is a quaternary ammonium cation, with two ethyl arms, one benzyl and one larger amide one, and usually comes as a benzoate - a salt of benzoic acid.
Denatonium benzoate’ s repellent qualities equally help fight rodents such as rats or mice.
Denatonium benzoate is a potent bitter taste receptor agonist widely used for activation of different cell pathways.
Taste signals have been associated with food recognition and food avoidance, and the bitter taste causes a deterrent response and is supposed to protect chickens from consuming poisons and harmful toxic substances.
The results of the study revealed that dietary supplementation with medium and high doses of Denatonium benzoate induced apoptosis and autophagy, respectively, damaging epithelial cells of the heart and kidneys and reducing the growth.
Denatonium benzoate's claim to fame is simple, unpleasant but valuable - Denatonium benzoate is the most bitter substance yet discovered.This unreactive, colourless, odourless compound was first produced accidentally in 1958 by Scottish pharmaceutical manufacturer T & H Smith, later Macfarlan Smith, where researchers were experimenting with variants of an anaesthetic for dentists called lignocaine.
Denatonium benzoate was soon discovered that just a few parts per million of Denatonium benzoate were enough for this aggressively unpleasant compound to render a substance distasteful to humans.
Denatonium benzoate is now known as the world's most bitter compound.
The vast majority of its applications are related to its bitter flavor.
Denatonium benzoate 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.
Denatonium benzoate 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,
Denatonium benzoate was first synthesized in the 1950s and is usually prepared by reacting denatonium chloride with benzyl benzoate.
Denatonium benzoate is also available under the trade name Denatonium benzoate, which is a token of the words pain and rex for the king.
Denatonium benzoate is a salt compound with an inert anion such as benzoate or saccharide.
Denatonium benzoate is structure is similar to lidocaine and is closely related to Novocain and benzocaine.
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.
Denatonium benzoate 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.
Denatonium benzoate, usually available as Denatonium benzoate (trade names Denatonium benzoate) 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 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 is used as an alcohol denaturant, possibly a combination of 20 in United States pictures.
Denatonium benzoate is used in many personal care products such as make-up, lotion, fragrance, shaving, oral care, skin care and hair care products, where it functions as antifoam, cosmetic astringent, solvent and viscosity reducing agent.
In OTC antimicrobial drug products, Alcohol also functions as an antimicrobial agent to kill germs.
Denatonium benzoate is the bitterest known compound.
Denatonium benzoate was discovered in 1958 by Macfarlan Smith of Edinburgh, Scotland, during research on local anesthetics.
Dilutions as little as 10 ppm are unbearably bitter for most people.
Denatonium benzoate salts are usually colorless and odorless solids, but are often sold as solutions.
Denatonium benzoate, an extremely bitter derivative of lignocaine, has been used worldwide as an alcohol denaturant for over 30 years.
The recent recognition of its application to deter ingestion of potentially toxic products has led to its use as an inert ingredient in pesticides, automotive chemicals and household items.
A standard research protocol has been developed to determine the applicability of the use of Denatonium benzoate in certain formulations.
This ensures compatibility, stability and optimum Denatonium benzoate concentration to affect a bitter taste in the formulated product.
Denatonium benzoate is currently known as the world's most painful ingredient.
The vast majority of its applications are related to its bitter taste.
Strychnine is a cheap and efficient alternative to its counterparts such as bitter lignin, quinine, wood song glycosides, saponins grapefruit.
Denatonium benzoate is widely used as a deterrent agent to prevent people from eating other toxic but tasteless substances.
For example, industrial alcohol, which tastes similar to ordinary wine, antifreeze, paint, toilet cleaners, animal dispersion, liquid soaps and shampoos, has been added to ethylene glycol or methanol.
Among these flavors, Denatonium benzoate with a bitter taste cause the most reactions.
Sensitivity to bitter flavors depends on genetics: The TAS2R38 gene determines a person's ability to detect bitterness associated with substances such as quinine, a component in tonic water.
Denatonium benzoate is also the standard for this kind of bitter taste.
At a concentration of 0.008 moles per cubic meter, the human tongue can detect the presence of quinine.
Denatonium benzoate also applies to outdoor cables and wires to prevent rodents from chewing on parts and equipment.
Denatonium benzoate is a deterrent agent added to various pesticides, plant food sticks, and rodenticides to suppress swallowing, especially when young children come into contact with these toxic substances.
Until now, the most common use of Denatonium benzoate is to denature alcohol so that Denatonium benzoate is unfit for human consumption and is exempted from the tariffs ormally valid for alcohol.
In recent years, Denatonium benzoates inclusion in household products, garden products, and cosmetics has been intensely promoted to prevent children from accidentally swallowing it.
A concentrated solution of Denatonium benzoate is available in the USA, which will be sold directly to the public in addition to household products.
Efficacy and safety studies on Denatonium benzoate are limited and may be subject to different interpretations when considered in the context of a potential bittering.
For Denatonium benzoate, a concentration of 0.000008 moles per cubic meter can be noticed by humans.
Bitter substances such as Denatonium benzoate are useful as deterrent additives to prevent accidental ingestion of dangerous automotive compounds.
In Europe and some US states, ethylene glycol or Denatonium benzoate must be added to antifreeze and windshield washer fluids.
Common household products such as window cleaners, disinfectants, laundry detergents, and insecticides contain certain amounts of Denatonium benzoate to deter oral consumption.
Denatonium benzoate is also added to special nail polish ingredients as a repellent to avoid the child's bad finger biting.
Denatonium benzoate is stable up to 140 ° C and over a wide pH range.
Denatonium benzoate should be stored in a cool and dry place in a well-sealed container (such as steel with polyethylene lining).
Aqueous or alcoholic solutions retain their pain for several years, even when exposed to light.
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.
Denatonium benzoate is generally regarded as having the most bitter taste of any compound known to science.
Denatonium benzoate is sold under the trade name of Denatonium.
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.
Denatonium benzoate is a bittering agent.
Denatonium benzoate is considered the bitterest chemical compound with a range of uses in the manufacture of cleaners, automotive supplies as well as health and beauty items.
Commercially, Denatonium benzoate is available as a white crystalline powder, but Denatonium benzoate granules or solutions are also available.
Humans can typically sense sweet, sour, salty, savory and bitter-tasting stuff.
Of these flavors, bitter-tasting chemicals elicit the most reaction.
The 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.
Denatonium benzoate is applied to the surfaces of toys as a painful substance to prevent significant consumption of hazardous substances.
Uses of Denatonium Benzoate:
Denatonium benzoate can be used in animal repellents to prevent animals from chewing or consuming treated items.
In products like varnishes and wood coatings, Denatonium benzoate can deter individuals from attempting to ingest or chew on treated surfaces.
In industrial settings, Denatonium benzoate can be added to surfactants and detergents to prevent misuse and accidental ingestion.
Denatonium benzoate is used worldwide as a denaturant for alcohol.
Denatonium benzoate is included in the FDA Inactive Ingredients Database (topical gel and solution).
In some cases, Denatonium benzoate's used in dental products like mouthguards and orthodontic devices to discourage biting or chewing on them.
Denatonium benzoate is used in the following products: washing & cleaning products, biocides (e.g. disinfectants, pest control products), plant protection products, polishes and waxes, anti-freeze products, air care products, coating products, fillers, putties, plasters, modelling clay, finger paints, polymers, water softeners and cosmetics and personal care products.
Denatonium benzoate is used in the following areas: agriculture, forestry and fishing and health services.
Denatonium benzoate is used for the manufacture of: chemicals, machinery and vehicles, plastic products, mineral products (e.g. plasters, cement), electrical, electronic and optical equipment and furniture.
Other release to the environment of Denatonium benzoate is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
The bitterest compound known Denatonium benzoate is used as an alcohol denaturant and flavor in pharmaceuticals.
Denatonium benzoate is also used in antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps and shampoos.
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.
Further, Denatonium benzoate is used in air care products.
Denatonium benzoate acts as H1 antihistamine.
In addition to this, Denatonium benzoate is used as a disinfectant.
Denatonium benzoate is often added to various alcohol-based products like hand sanitizers, rubbing alcohol, and disinfectants to discourage ingestion, especially in situations where these products might be mistaken for consumable beverages.
Denatonium benzoate is used in products like engine coolant and antifreeze to prevent accidental ingestion by humans or animals.
Denatonium benzoate is a bittering agent used to make toxic products more difficult to ingest.
Some aerosol sprays, such as air fresheners and cleaning sprays, contain Denatonium benzoate to prevent inhalation or ingestion.
Denatonium benzoate is used in the following products: washing & cleaning products, polymers, biocides (e.g. disinfectants, pest control products), polishes and waxes, fertilisers, anti-freeze products and plant protection products.
Release to the environment of Denatonium benzoate can occur from industrial use: formulation of mixtures and formulation in materials.
Denatonium benzoate is used in the following products: washing & cleaning products, polymers, biocides (e.g. disinfectants, pest control products), plant protection products, anti-freeze products and polishes and waxes.
Denatonium benzoate is used in the following areas: agriculture, forestry and fishing and health services.
Denatonium benzoate is used for the manufacture of: plastic products, machinery and vehicles and electrical, electronic and optical equipment.
Release to the environment of Denatonium benzoate can occur from industrial use: in processing aids at industrial sites, in the production of articles and for thermoplastic manufacture.
In some regions, Denatonium benzoate is added to fuel products to prevent fuel theft and to reduce the risk of fuel ingestion, which can be harmful.
Denatonium benzoate is a bittering agent which is used to give a bitter taste to toxic products in order to make the product more difficult to ingest.
Examples of products which contain Denatonium benzoate are: antifreeze, detergents, floor cleaner, paint stripper and toilet cleaner.
Denatonium benzoate is added to numerous household products, such as cleaning agents, detergents, and solvents, to discourage accidental ingestion.
This helps prevent poisoning, particularly in homes with children or pets.
Some automotive products, including antifreeze and windshield washer fluids, contain Denatonium benzoate to deter accidental ingestion, which can be toxic.
Insect repellents, pet shampoos, and other products that pets might be tempted to lick or consume sometimes contain Denatonium benzoate to deter this behavior.
Some stationery items, such as glues and correction fluids, use Denatonium benzoate to prevent misuse by children.
In healthcare settings, Denatonium benzoate can be used to discourage the ingestion of certain medical products or solutions.
Denatonium benzoate is used in certain paints and coatings to make them unpalatable.
This discourages individuals from consuming paint, which can be hazardous.
Nail polish removers may contain Denatonium benzoate to make them taste extremely bitter, preventing individuals, especially children, from accidentally ingesting them.
Some personal care products like nail polish, perfumes, and cosmetics may include Denatonium benzoate to make them unappealing to taste, reducing the risk of misuse.
In specific medications and pharmaceutical formulations, Denatonium benzoate is used to deter misuse or accidental ingestion, particularly in cases where the drug could be harmful if ingested.
In some pesticides, Denatonium benzoate is used to prevent oral ingestion.
This safeguards against accidental poisoning, particularly in cases where pesticides might be attractive to children or animals.
In certain therapeutic contexts, Denatonium benzoate is used in behavioral therapy.
By associating a negative, extremely bitter taste with a specific behavior or habit (e.g., smoking or nail-biting), it aims to create a psychological aversion to that behavior.
Denatonium benzoate may be added to some adhesives to deter people from attempting to chew or ingest adhesive products.
Beyond cleaning agents and detergents, Denatonium benzoate can also be found in various other household chemicals like drain cleaners, toilet bowl cleaners, and paint thinners.
Some insecticides and rodenticides use Denatonium benzoate to prevent ingestion, especially by children or pets.
Certain garden products, such as fertilizers and herbicides, contain Denatonium benzoate to reduce the risk of ingestion.
In some regions, Denatonium benzoate's added to tobacco products like cigarettes and chewing tobacco to discourage ingestion, particularly by children and young individuals.
Denatonium benzoate is added to denatured alcohol to make it unpalatable.
This is important in preventing the consumption of alcohol that is not meant for drinking, such as industrial or cleaning purposes.
Bittering Agent:
Denatonium benzoate is added to products like antifreeze, solvents, and household cleaners to make them taste unpleasant and discourage accidental ingestion.
Deterrent in Products:
It is used in products like nail-biting deterrents and pet deterrents to prevent undesirable behaviors.
Pharmaceuticals:
Occasionally used in pharmaceuticals to prevent accidental overdoses.
Productions Process of Denatonium Benzoate:
Synthesis:
Chemical Synthesis:
Starting Materials:
The synthesis typically involves the reaction of Denatonium benzoate with benzoic acid.
Denatonium benzoate is often produced from denatonium chloride and sodium hydroxide.
Benzoic Acid is a common organic acid used in the reaction.
Reaction:
Denatonium Hydroxide + Benzoic Acid → Denatonium Benzoate + Water
Purification:
Crystallization:
After the reaction, the product is usually crystallized from a suitable solvent to purify denatonium benzoate.
The choice of solvent and crystallization conditions are critical to achieve high purity.
Filtration:
The crystalline product is separated from the solvent and other impurities through filtration.
Drying:
The filtered product is dried to remove residual solvents and moisture, often in a vacuum oven or desiccator.
Quality Control:
Testing:
The purified Denatonium benzoate is tested for purity, appearance, melting point, and solubility according to the specifications.
Assay:
Ensures the active ingredient is within the acceptable range (typically 98.0% to 101.0%).
Heavy Metals, Arsenic, and Other Impurities:
Tested to meet regulatory and safety standards.
Formulation:
Blending:
The purified Denatonium benzoate is blended with other ingredients to form the final product.
This might include stabilizers or carriers depending on the intended application.
Packaging:
The final product is packaged in appropriate containers, often as a powder or in solution form, with proper labeling and safety information.
Regulatory Compliance:
Certification:
The production process and the final product must comply with relevant regulations and standards (e.g., FDA, REACH, etc.).
Certificates of Analysis (CoA):
Provided to confirm that the product meets specified standards.
Handling and Storage of Denatonium Benzoate:
Handling:
Personal Protective Equipment (PPE):
Use gloves and safety goggles to avoid direct contact with the skin and eyes.
Ventilation:
Work in a well-ventilated area to avoid inhaling dust or fumes.
Storage:
Denatonium benzoate is stable up to 140°C and over a wide pH range.
Denatonium benzoate 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.
Conditions:
Store in a cool, dry place away from direct sunlight.
Containers:
Keep in a tightly sealed container to avoid contamination and degradation.
Stability and Reactivity of Denatonium Benzoate:
Stability:
Denatonium benzoate is stable under normal conditions.
Reactivity:
Generally non-reactive but should be kept away from strong acids and bases.
Safety Profile of Denatonium Benzoate:
Inhalation of Denatonium benzoate dust or aerosols may irritate the respiratory tract, leading to coughing or throat irritation.
Proper ventilation in areas where Denatonium benzoate is handled can help minimize this risk.
Denatonium benzoate is extremely bitter and can cause extreme discomfort and nausea if ingested.
While it is not toxic at the concentrations typically used in products, accidental ingestion can lead to adverse reactions such as vomiting and gastrointestinal discomfort.
Contact with Denatonium benzoate can cause eye and skin irritation.
Denatonium benzoate is essential to use personal protective equipment (PPE) such as gloves and safety goggles when handling the substance to prevent skin and eye contact.
While Denatonium benzoate is not known to pose significant environmental hazards, large-scale spills or releases into waterways could potentially have ecological consequences.
Denatonium benzoate is essential to handle and store the substance properly to prevent environmental contamination.
Denatonium benzoate is generally regarded as a nonirritant and nonmutagenic substance.
First Aid Measures of Denatonium Benzoate:
Inhalation:
Move to fresh air and seek medical attention if irritation or respiratory issues persist.
Skin Contact:
Wash affected area with soap and water.
Seek medical attention if irritation continues.
Eye Contact:
Rinse eyes with plenty of water for at least 15 minutes and seek medical attention immediately.
Ingestion:
If ingested, do not induce vomiting.
Rinse mouth with water and seek medical attention immediately.
Firefighting Measures of Denatonium Benzoate:
Extinguishing Media:
Use appropriate extinguishing media for surrounding materials.
Denatonium benzoate itself is not flammable.
Firefighting Procedures:
Wear self-contained breathing apparatus and protective clothing in case of a fire involving Denatonium benzoate.
Accidental Release Measures of Denatonium Benzoate:
Personal Precautions:
Wear protective equipment to avoid contact.
Environmental Precautions:
Prevent the chemical from entering drains or water sources.
Cleanup Methods:
Sweep up and dispose of the material according to local regulations.
Clean the area with water and soap.
Exposure Controls/Personal Protection of Denatonium Benzoate:
Exposure Limits:
There are no specific exposure limits for Denatonium benzoate, but general hygiene practices should be followed.
Engineering Controls:
Ensure adequate ventilation in areas where Denatonium benzoate is used.
Personal Protective Equipment (PPE):
Wear gloves, safety goggles, and masks if necessary.
Identifiers of Denatonium Benzoate:
IUPAC Name: Denatonium benzoate
Chemical Formula: C28H34N2O3
Molecular Weight: Approximately 442.6 g/mol
CAS Number: 3734-33-6
EC Number: 223-095-5
PubChem CID: 2867
ChemSpider ID: 2771
SMILES Notation: CC(C)(C)C1=CC2=C(C=C1)C(=CC=C2)N(C)C3=CC=C(C=C3)C(=O)O
InChI Key: NXJBLXYREWORLT-UHFFFAOYSA-N
Ptoperties of Denatonium Benzoate:
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℃
Chemical Name: Denatonium benzoate
Chemical Formula: C28H34N2O3
Molecular Weight: Approximately 442.6 g/mol
Appearance: White, crystalline powder
Odor: Odorless or faintly aromatic
Taste: Extremely bitter (one of the most bitter substances known)
Specifications of Denatonium Benzoate:
Appearance: White crystalline powder.
Purity: Typically, Denatonium benzoate is required to be > 98% pure, with specifications often ranging between 98% and 99.5%.
Melting Point: Approximately 160-165°C (320-329°F).
Solubility:
Water: Sparingly soluble (less than 1% by weight).
Ethanol: Soluble.
Acetone: Soluble.
Odor: Odorless or faintly aromatic.
pH of 1% Solution: Usually neutral to slightly acidic (around pH 6-7).
Loss on Drying: Typically less than 1.0% when dried at 105°C for 1 hour.
Heavy Metals: Usually specified to be below 10 ppm.
Arsenic: Generally less than 2 ppm.
