DENATONIUM BENZOATE
DENATONIUM BENZOATE
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, this compound is available as a white crystalline powder, but denatonium benzoate granules or solutions are also available.
CAS# 3734-33-6
Denatonium (benzoate salt)
EC / List no.: 223-095-2
CAS no.: 3734-33-6
Mol. formula: C28H36N2O4
Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate
Denathonium benzoate
Denatonium benzoate
Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate (1:1)
[2-(2,6-dimethylanilino)-2-oxoethyl]-diethyl-(phenylmethyl)azanium benzoate
benzyl({[(2,6-dimethylphenyl)carbamoyl]methyl})diethylazanium benzoate hydrate
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium;benzoate
Benzyldiethyl [(2,6 xylylcarbamoyl) methyl] ammonium benzoate
BENZYLDIETHYL((2,6-XYLYLCARBAMOYL)METHYL)AMMONIUM-BENZOATE
Benzyldiethyl(2,6-xylylcarbamoyl)- methylammoniumbenzoat
DENATONIUM BENZOATE
Denatonium Benzoate
Denatonium benzoate
denatonium benzoate
DENATONIUM BENZOATE
Denatonium benzoate
N-[2-[(2,6-Dimethylphenyl)amino]-2-oxoethyl]-N,N-diethylbenzenemethanaminium benzoate
N-benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethanaminium benzoate hydrate
phenylmethyl-[2- [(2,6-dimethylphenyl)amino]- 2-oxoethyl]-diethylammonium benzoate
phenylmethyl-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-diethylammonium benzoate
Bitrex, the bitterest known substance, renders harmful chemicals undrinkable and has helped reduce poisoning incidents.
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 Benzoate
CAS: 3734-33-6
Denatonium benzoate is the most bitter chemical compound known.
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 it.
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, 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.
It 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.
It is not known to pose any long-term health risks.
The name denatonium is a portmanteau word reflecting the substance’s primary use as a denaturant and its chemical nature as a cation, hence the New Latin suffix -onium.
Structure and physical properties
Denatonium is a quaternary ammonium cation. It 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.
Applications
The bitterness of the compound guides most applications of denatonium. Denatonium benzoate is used to denature ethanol so that it is not treated as an alcoholic beverage with respect to taxation and sales restrictions.
One designation in particular, SD-40B, indicates that ethanol has been denatured using denatonium benzoate.
Denatonium is commonly included in placebo medications used in clinical trials to mimic the bitter taste of certain medications.
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.
It is also added to less hazardous aerosol products (such as gas dusters) to discourage inhalant abuse of the volatile vapors.
In 1995, the U.S. state of Oregon required that denatonium benzoate be added to products containing sweet-tasting ethylene glycol and methanol such as antifreeze and windshield washer fluid to prevent poisonings of children and animals.
In December 2012, U.S. manufacturers voluntarily agreed to add denatonium benzoate to antifreeze sold nationwide.
Animals are known to have different sensitivities to the effects of denatonium.
It is used in some animal repellents (especially for such large mammals as deer).
It has been used to safeguard rat poisons from human consumption, as humans are able to detect denatonium at much lower concentrations than rodents.[11]
The repulsive taste of denatonium can be used as a deterrent on products not designed for consumption, and/or are harmful upon consumption.
Famously, the Nintendo Switch game cards are coated in denatonium benzoate to prevent young children from consuming them
Denatonium benzoate is used in the food and beverage industry as well as a solvent in many household and personal care products.
INCI name: DENATONIUM BENZOATE
EINECS/ELINCS number: 223-095-2
Bio-compatible (COSMOS Reference)
Its functions (INCI)
Denaturant : Makes cosmetics unpleasant. Mainly added to cosmetics containing ethyl alcohol
Masking : Reduces or inhibits the odor or basic taste of the product
ALSO KNOWN AS
denatonium saccharide; Denatonium
N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-benzenemethanaminium,
monobenzoate; Lidocaine benzyl benzoate; NSC 157658; WIN 16,568;
Use: Denatonium benzoate is a stimulant of the bitter taste receptors used as aversive agents (bitterants) to prevent inappropriate ingestion.
N,N-Diethyl-N-[(2,6-dimethylphenyl¬carbamoyl)¬methyl]¬benzyl¬ammonium benzoate;
Benzyldiethyl(2,6-xylyl¬carbamoyl¬methyl)¬ammonium benzoate;
phenylmethyl-[2- [(2,6-dimethylphenyl)amino]- 2-oxoethyl]-diethylammonium benzoate; Bitrex
Technical Data
CAS Number: 3734-33-6
Molecular Formula: C28H34N2O3
Molecular Weight: 446.58
Beilstein Registry Number: 8179408
EC Number: 223-095-2
Denatonium, usually available as Denatonium and as Denatonium Saccharide, is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide.
They are used as aversive agents (bitterants) to prevent inappropriate ingestion of chemical and hazardous products.
Denatonium is used in denatured alcohol, anti-freeze, respirator mask fit-testing, animal repellents, liquid soaps, and shampoos.
APPLICATION
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 (substance)
Synonyms:
lidocaine benzyl benzoate
benzyl diethyl [(2,6-xylylcarbamoyl)methyl] ammonium benzoate
References:
CAS n° 3734-33-6
EINECS n° 223-095-2
Main characteristics:
Most bitter chemical substance known
Suitable solution to avoid an accidental ingestion of hazardous products by children and pets
A small quantity is efficient (only a couple of ppm) to make your product safer
Essential product in alcohol denaturating
Denatonium Benzoate, a well-known bittering agent
Most bitter chemical substance known
Efficient solution that can be added to most compatible products
A small quantity is efficient (only a couple of ppm) to make your product safer
Aspect: white, odourless, colourless, in powder or granules
As of today, the poison statistics by accidental ingestion of chemical products such as detergents, cosmetics, antifreezes, or phytosanitary products (i.e products used to treat plants), show that too many people is still affected each year, especially young children willing to taste any reachable object and who are not yet able to differentiate non-food products from food products.
When added to the above mentioned dangerous chemical products, Denatonium Benzoate plays the role of a deterrent and contributes to prevent from hazardous ingestions by giving an extremely bitter and unpleasant taste to the products it is added to.
Increasingly, companies decide to add Denatonium Benzoate to their manufacturing process to prevent accidental ingestion of household or garden products and provide maximum security to their customers.
Denatonium Benzoate is one of the most bitter substances known and is equally used for many other purposes.
It is indeed one of the substances most used for the denaturing of alcohol (especially ethanol) in order to make it undrinkable and ready for industrial uses. Denatonium Benzoate is also found in nail polish, where it helps to fight against onychophagy (i.e. severe nail biting). Its bittering properties make of Denatonium Benzoate an excellent repellent which, once added to phytosanitary products, contribute to deter animals from feeding on treated trees and plants. Its repellent qualities equally help to fight against rodents such as rats or mice.
Denatonium benzoate is a strong bitter taste receptor agonist, extensively used for its activation of different cell pathways.
Taste signals have been associated to food recognition and avoidance, and bitter taste provokes an aversive reaction and is assumed 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 damaged the epithelial cells of the heart and kidneys by inducing apoptosis and autophagy and reduced the growth of chickens, respectively
According to Chemistry World, denatonium benzoate was an accidental formulation by researchers at T & H Smith, a Scottish pharmaceutical firm that was the precursor for Macfarlan Smith Ltd.
In 1958, staff at the laboratory was working with lignocaine, a dental anesthetic, when they discovered the extreme bitterness of denatonium benzoate in powder form.
Due to the extreme taste, denatonium benzoate was used as an aversive agent.
It is also available under the trade name Bitrex, which is a portmanteau of the words bitter and rex for king.
The first known application for Bitrex was as an aversant for pigs that were cannibalizing their own tails or those of other pigs.
The chemical database PubChem assigned a chemical identification number or CID of 19518 to denatonium.
It 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.
Its structure is similar to lidocaine and is closely related to Novocain and benzocaine.
It is odorless, colorless and non-reactive, making it a suitable additive that does not interfere with the primary purpose of the base compound.
Denatonium benzoate (Bitrex) has been used in the United States for over 20 years as an alcohol denaturant.
How it Works
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.
It 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.
Applications
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.
It is applied on surfaces of toys as a bittering agent to prevent substantial consumption of hazardous materials.
It 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 it 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. It acts as a repellant when applied to young shoots, branches and other surfaces to discourage nibbling by animals, thereby preventing damage to property.
In recent years, it 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.
Currently available, admittedly limited data indicate that denatonium benzoate may actually have a low toxicity profile.
Considering its wide availability as a denaturant for alcohol, it is surprising that human toxicity has been reported only once.
However, denatonium toxicity may have been unrecognized because it is usually not included on product-ingredient lists since it represents a small percentage of the total chemical make-up of the product.
No data exist on acute ocular or inhalation exposure in humans, chronic skin exposure in humans or animals, or chronic inhalation exposure in humans or animals.
Its safety on broken or abraded skin has not been investigated.
There are no teratogenicity studies.
In July 1991, The American Academy of Veterinary and Comparative Toxicology passed a resolution to encourage the use of a bittering agent to limit the ingestion of hazardous materials by companion animals.
Rodgers expressed the view that some of the products, such as caustics and hydrocarbons, to which aversive agents might be added may produce toxicity with a single swallowing and it is unlikely that the addition of an adversive agent would have a beneficial effect on the outcome of such ingestions.
He suggested that addition of denatonium benzoate might actually increase the potential for toxicity of such ingestions because vomiting might increase the risk of aspiration.
He therefore recommended the use of denatonium benzoate in a limited number of products including those containing ethylene glycol, methanol and toxic pesticides.
In summary, denatonium benzoate appears to be safe when used at low concentrations as an aversive agent.
However, there are limited data about whether aversive agents have an impact on either the number or the severity of pediatric ingestions, and its use should not be a substitute for other preventive measures such as child-resistant closures.
enatonium is a rather more convenient name than phenylmethyl-[2- [(2,6-dimethylphenyl)amino]-2-oxoethyl]-diethylammonium.
It 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. Its 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.
It 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.
Bitterness is one of the five basic tastes alongside sweetness, saltiness, sourness and the savoury taste umami.
Although it is a myth that the tongue has different receptors for the tastes in specific regions of its surface, our tongues are more sensitive to some tastes than others – and bitterness is the one that grabs our attention most strongly.
It seems likely that this is because many toxic substances stimulate the bitter taste reaction, though perversely some substances many of us like to consume – coffee, hops in beer and the quinine in tonic water, for instance – also have a bitter kick.
Usually these are acquired tastes: children will have an aversion to them, but as we get older, our brains can override the palate to help us appreciate more sophisticated taste combinations.
To be able to respond to bitter tastes, we have a collection of genes that encode for a total of 25 different taste receptors, each reacting to a different class of compound.
Around a quarter of the population can’t taste the compound propylthiouracil, which is similar to the compounds that produce the classic bitter flavours of cabbage and tonic water.
The ability to detect this taste (and this kind of bitterness) is dependent on a single gene, TAS2R38.
A single letter variation in that gene – a single nucleotide polymorphism – is responsible for whether or not a person can detect such bitterness.
Quinine, the archetypal bitter substance associated with this gene, is used as the benchmark for bitterness, and is helpful in demonstrating just how strong denatonium benzoate is.
The human tongue can pick up the bitter kick of quinine at a concentration of around 0.008 moles per cubic metre.
By contrast, denatonium benzoate requires a thousandth of that concentration to be detected.
Our outstanding reaction to denatonium benzoate is likely to be an accidental function of the way the TAS2R taste receptors on the tongue react to this particular compound.
But this is an accident that has found plenty of use, as denatonium benzoate is marketed under names like Bitrex, BITTER+PLUS and Aversion, which are all varieties of bitterants or aversive agents.
The idea is simple – if you have something that may be consumed but shouldn’t be, you add some denatonium benzoate and even small quantities of it will put people off.
Children, who inevitably are the most likely to try to consume substances they shouldn’t, with as many as 30,000 a year taken to hospital in the UK alone with suspected poisoning, seem particularly sensitive to the bitter attack of denatonium, making it ideal for the job.
Some of the applications are straightforward – in the otherwise sweet-tasting but poisonous antifreeze ethylene glycol, for instance, and in rat poison (luckily rat tongues are a lot less sensitive to the compound). Rather more sneakily, ethanol can be ‘denatured’ by adding denatonium, making it undrinkable.
This means it can be sold without the large tax burden that usually accompanies an alcoholic drink, when the alcohol is to be used for cleaning or as fuel – a particularly common application with the increasing use of bioethanol.
Perhaps the most direct application of denatonium is to help those who can’t prevent themselves from nibbling their nails.
A mixture containing a small amount of the compound is painted on and when the sufferer attempts to bite their nails – often doing it unconsciously – the bitter taste quickly deters them.
Bitrex is…
Denatonium Benzoate – to give it its full, technical name. Ironically, that’s a bit of a mouthful. So we call it Bitrex.
The bitterest substance known to man, woman or child. That’s according to The Guinness World Records.
A substance that’s put into household, garden and automotive products to ensure that if a child or animal ever tried to swallow it, they would spit it straight out before they could be poisoned.
Completely harmless if consumed. It just tastes really, really horrible.
A lifesaver. Literally.
The product of a happy accident. Bitrex was discovered in 1958 by a team of Macfarlan Smith scientists who were working on a new local anaesthetic. Our chemists realised immediately that they had found a remarkable substance – the world’s most bitter material – and quickly put it to good use…
Helping to make accidental poisoning a thing of the past.
Bitrex is not…
A substitute for other common sense precautions for preventing poisoning, such as keeping chemicals out of a child’s reach, using safety closures properly and reading labels carefully.
But we pioneered this child safety additive precisely because we know what it’s like to be a parent. We understand that parents get harassed, tired, and up to their eyes. And that is why Bitrex is there. For the moments of inattention when most accidents happen.
Denatonium Benzoate
Denatonium Benzoate with CAS 3734-33-6 is a bittering agent used as an aversion additive in various chemical and manufactured products
The primary use of DNB 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).
This chemical is not intended for use in any products or chemicals in which the intention is human ingestion.
Applications
Antifreeze / engine coolants
Windshield wiper fluids
Personal care and cosmetic products such as e.g. nail polish removers
Denatured alcohols such as ethanol
Hand sanitizer
Rodent baits
Pesticides
Synonyms:
ammonium, benzyldiethyl((2,6-xylylcarbamoyl)methyl)-, benzoate
benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate
benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate
benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate (1:1)
benzyl diethyl (2,6-xylyl carbamoyl methyl) ammonium benzoate
benzyl-[(2,6-dimethylphenylcarbamoyl)methyl]diethylammonium benzoate
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium benzoate
N- benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethanaminium benzoate
benzyldiethyl((2,6-xylylcarbamoyl)methyl)ammonium benzoate
benzyldiethyl(2,6-xylyl- carbamoyl- methyl)- ammonium benzoate
benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate
bitrex
denatoniumbenzoate
N,N- diethyl-N-[(2,6-dimethylphenyl- carbamoyl)- methyl]- benzyl- ammonium benzoate
N-(2-((2,6- dimethyl phenyl)amino)-2-oxoethyl)-N,N-diethyl benzene methanaminium benzoate
N-(2-((2,6- dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme- thanaminium benzoate
((2,6- xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate
Ethanol or ethyl alcohol, sometimes just called Alcohol, is the alcohol found in alcoholic beverages. In the United States alcoholic beverages (liquor, wine, beer, etc.) are heavily taxed.
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. Government’s Alcohol and Tobacco Tax and Trade Bureau (TTB). 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.
Denatured alcohol is generally identified as Alcohol Denat. or specially Denatured (SD) Alcohol.
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.
Why is it used in cosmetics and personal care products?
Denatured Alcohol is used in many personal care product types including makeup, lotions, fragrance, shaving, oral care, skin care and hair care products where it functions as an antifoaming agent, cosmetic astringent, solvent and viscosity decreasing agent.
In OTC antimicrobial drug products, Alcohol also functions as an antimicrobial agenthttp://www.cosmeticsinfo.org/sites/all/modules/contrib/lexicon/imgs/lexicon.gif to kill germs.
Denatonium, usually available as denatonium benzoate (or under trade names such as Bitrex or Aversion) and as denatonium saccharide, is the most bitter compound known. It was discovered in 1958 during research on local anesthetics by Macfarlan Smith of Edinburgh, Scotland. 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 to prevent accidental ingestion. Denatonium is used in denatured alcohol, antifreeze, nail biting preventions, animal repellents, liquid soaps, and shampoos. It is not known to pose any long-term health risks although exposure may be irritating and unpleasant.
Structure and physical properties
Denatonium is a quaternary ammonium cation. It 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.
Applications
The bitterness of the compound guides most applications of denatonium. Denatonium is used to denature ethanol so that it is not taxed as an alcoholic beverage. One designation in particular, SD-40, indicates that ethanol has been denatured using denatonium. In fact, the common name for this chemical, denatonium alludes to this application.
Denatonium also discourages consumption of harmful alcohols like methyl alcohol and ethylene glycol. Denatonium is therefore often used in rubbing alcohol as an inactive ingredient. It is also added to all kinds of harmful liquids including solvents, paints, varnishes, toiletries, and other household products.
Since 1995, when the State of Oregon required that it be added to antifreeze and windshield wiper fluid, the compound has been increasingly found in these substances throughout the world. The addition of denatonium is credited with saving children and animals who might otherwise drink sweet antifreeze or wiper fluid and get ethylene glycol or methanol poisoning respectively.
Other uses include nail polish for preventing nail biting, and as animal repellent (especially for big game like deer).
It should be noted that animals are known to have different sensitivities to the effects of denatonium. It has been used to safeguard rat poisons from human consumption, so presumably rats are not deterred by it, although there is evidence that a small percentage of rodents do avoid such baits. Some cats have been known to be tempted by them it may not be as effective a deterrent for cats as it is for humans, or perhaps some cats are not deterred due to a genetic factor similar to that affecting human perceptions of the taste of phenylthiocarbamide.
Denatonium benzoate (THS-839) is the most bitter chemical compound known,used as aversive agents (bitterants) to prevent inappropriate ingestion. Denatonium benzoate (THS-839) is used in denatured alcohol, antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps, and shampoos.
1950
223-095-2 [EINECS]
3734-33-6 [RN]
8179408
Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl- benzoate (1:1) [ACD/Index Name]
Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate
Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate (1:1)
Benzoate de denatonium [French] [INN]
benzoate de dénatonium [French] [INN]
Benzoate de N-benzyl-2-[(2,6-diméthylphényl)amino]-N,N-diéthyl-2-oxoéthanaminium [French] [ACD/IUPAC Name]
Benzoato de denatonio [Spanish] [INN]
Benzyldiethyl(2,6-xylyl??carbamoyl??methyl)??ammonium benzoate
Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate
BO6650000
denatonii benzoas [Latin] [INN]
Denatonium (benzoate salt)
denatonium benzoate [INN] [NF]
Denatonium benzoate anhydrous
MFCD00031578 [MDL number]
N,N-Diethyl-N-[(2,6-dimethylphenyl??carbamoyl)??methyl]??benzyl??ammonium benzoate
N-Benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethanaminium benzoate [ACD/IUPAC Name]
N-Benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethanaminiumbenzoat [German] [ACD/IUPAC Name]
денатония бензоат [Russian] [INN]
بنزوات ديناتونيوم [Arabic] [INN]
苯甲地那铵 [Chinese] [INN]
((2,6-Xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate
[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-diethyl-(phenylmethyl)ammonium benzoate
[2-[(2,6-dimethylphenyl)amino]-2-oxo-ethyl]-diethyl-(phenylmethyl)ammonium benzoate
[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-diethyl-(phenylmethyl)azanium benzoate
[2-[(2,6-dimethylphenyl)amino]-2-oxo-ethyl]-diethyl-(phenylmethyl)azanium benzoate
2-[benzyl(diethyl)azaniumyl]-N-(2,6-dimethylphenyl)ethanimidate
Ammonium, benzyldiethyl((2,6-xylylcarbamoyl)methyl)-, benzoate
Ammonium, benzyldiethyl[(2,6-xylylcarbamoyl)methyl]-, benzoate
Anispray
Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate
benzoate de dénatonium
benzoato de denatonio
Benzoic acid [ACD/Index Name] [ACD/IUPAC Name] [USP] [Wiki]
Benzyl-[(2,6-dimethylphenylcarbamoyl)methyl]diethylammonium benzoate
Benzyl-[(2,6-dimethylphenylcarbamoyl)-methyl]diethylammonium benzoate
benzyl-[2-(2,6-dimethylanilino)-2-oxo-ethyl]-diethyl-ammonium benzoate
benzyl-[2-(2,6-dimethylanilino)-2-oxo-ethyl]-diethyl-ammonium;benzoate
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium and benzoate
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium;benzoate
benzyl-[2-[(2,6-dimethylphenyl)amino]-2-keto-ethyl]-diethyl-ammonium benzoate
BENZYLDIETHYL [(2,6-XYLYLCARBAMOYL)-AMMONIUM BENZOATE
Benzyldiethyl {(2,6-xylylcarbamoyl) methyl} Ammonium Benzoate
BENZYLDIETHYL((2,6-XYLYLCARBAMOYL)METHYL)AMMONIUM BENZOATE
Benzyldiethyl(2,6-xylyl- carbamoyl- methyl)- ammonium benzoate
Benzyldiethyl(2,6-xylylcarbamoylmethyl)ammoniumbenzoate
Bitrex [Trade name] [Wiki]
denatonii benzoas
Denatonium Benzoate 25% in EG
denatonium benzoate, ???
Denatonium benzoate, granules
Denatonium benzoate, USP grade
Gori
Lidocaine benzyl benzoate
LIGNOCAINE BENZYL BENZOATE
N-(2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme- thanaminium benzoate
N,N-Diethyl-N-[(2,6-dimethylphenyl- carbamoyl)- methyl]- benzyl- ammonium benzoate
N,N-Diethyl-N-[(2,6-dimethylphenylcarbamoyl)methyl]benzylammoniumbenzoate
N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-benzenemethanaminium, monobenzoate
N-Benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethanaminium benzoate
денатония бензоат
بنزوات ديناتونيوم
苯甲地那铵
Denatonium benzoate is generally regarded as having the most bitter taste of any compound known to science.
It is sold under the trade name of Bitrex.
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.
It is used to prevent and treat by the purposes in the bactericide of the microbial plant disease of pathogenic preparing the invention discloses Denatonium Benzoate, the present invention passes through Toxicity Determination, it was demonstrated that Denatonium Benzoate has plant pathogenic fungi good inhibitory activity.
Denatonium Benzoate has the advantages that efficient and low toxicity, is suitable for the requirement of plant disease chemical prevention as bactericide.
The use of current bulk sterilization agent, causing the resistance to the action of a drug of pathogen strengthen, and traditional bactericide is big for environment pollution, residual height, directly threatens the food security of the mankind.
Denatonium Benzoate is a kind of degradable, pollution-free, environment amenable micromolecular compound, and its resistance to the action of a drug is poor, to non-target organism and person poultry safety, the high-quality of agricultural product and fruits and vegetables is ensure that, meets the requirement of sustainable development, it is studied and market application foreground is wide.
Denatonium Benzoate, also known as bitter, chemical name：Benzoic acid [2- [(2,6- 3,5-dimethylphenyl) amino] -2- oxo second Base]-N, N- diethylbenzyl ammoniums；
English name：Denatonium Benzoate、Benzenemethanaminium,N-[2- [(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-,benzoate；No. CAS：3734-33- 6；
Molecular formula：C28H34N2O3；
Molecular weight：446.5882；
White crystalline powder, fusing point be 164-168 DEG C, it is odorless, have bitter taste strongly, be highly soluble in water, ethanol, Ethylene glycol etc., its aqueous solution is in neutrality.
Denatonium Benzoate is to be currently known most bitter compound in the world, if setting quinine 1 on the basis of bitter degree, the bitter degree of this product is then 1000, and concentration is 10ppm solution, has been bitter obtain for vast majority of people
It can not stand, its overwhelming majority application is all relevant with its bitter taste, be brucine, guassin, quinine, the bent glucoside of wood, naringin Inexpensive efficient substitute.
Denatonium Benzoate be it is a kind of by quaternary ammonium salt cationic and inert anion such as benzoate anion ion or saccharin the moon from The quaternary ammonium salt that son is combined to form.
The structure of the material cation is similar with local anesthetic lidocaine, and its difference only exists
Many benzyl functional groups on the nitrogen-atoms of amino.
By as bitters (or aversive agent) in the usual commodity of Denatonium Benzoate and industrial goods, to avoid people from eating by mistake Other poisonous tasteless materials.
For example be added to industrial alcohol, the ethylene glycol similar to common drinks mouthfeel or methanol, it is antifreeze Among agent, paint, detergent for toilet, liquid soap and shampoo, the hair of people, the animal poisoning because caused by eating by mistake can be prevented
It is raw and prevent that animal from biting article (usage amount is 1~50ppm).
In addition special nail polish can be also added to In, the bad habit for avoiding children’s fingernail biting, and expel the expellant of large-scale wild beast.
Because concentration is extremely low, It is safety non-toxic under the conditions of.
Abstract
Denatonium Benzoate (DB), an extremely bitter lignocaine derivative, has been used world wide as an alcohol denaturant for over 30 years.
Recent recognition of its application for deterring ingestion of potentially toxic products has led to its introduction as an inert ingredient in pesticides, automotive chemicals and household goods. To determine the applicability of DB use in particular formulations, a standard research protocol has been developed.
This assures compatibility, stability and optimum DB concentration to effect a bitter taste in the formulated product.
This paper discusses compatibility issues, presents data on product stability and the use of human subjects for taste trials.
Keywords:
denatonium benzoate, bittering agent, poison prevention, ingestion deterrent, taste trial, pesticide poisoning
he 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
H1 antihistamine
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).
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,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.
LD50 (rabbit, oral): 0.508g/kg
LD50 (rat, oral): 0.584g/kg
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 (DB) is a bitterant used to reduce hazards and liability of accidental and intentional product ingestion.
Annual reports of the American Association of Poison Control Centers indicate ethylene glycol and methanol poisoning incidences, including fatalities and hospitalizations, continue to occur.
To mitigate poisoning severity to children and adults, addition of DB to these products has been explored and implemented by several manufactures.
The stability and efficacy of DB in products are discussed together with studies on toxicity and environmental impact.
It is concluded that DB renders these products bitter, is stable and compatible, and offers no significant toxicity or environmental hazards.
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 it.
Denatonium benzoate makes sweet but highly toxic products such as antifreeze and detergents taste foul.
By the addition of a denaturant, ethyl alcohol is made non-consumable (bad-tasting/offensive odor)
Aim of the denaturation is to escape the excise duty on drinkable alcohol, and therefore to make alcohol available at a reduced rate for industrial applications, such as the usage in cosmetics and technical applications.
A chemical compound accidentally discovered during work on dental anaesthetics almost 60 years ago is so bitter that it creates an overwhelming need to spit it out. The compound, known as Bitrex, discovered by Johnson Matthey scientists in Scotland, is transforming the safety of dangerous household, automotive and industrial chemicals worldwide.
The substance is the bitterest in the known universe and has been awarded a Guinness World record. Bitrex is harmless, but if ingested, will make the person who has consumed it spit it out quickly. A mere thimbleful of Bitrex can be tasted if added to an Olympic-sized swimming pool full of water.
DENATONIUM BENZOATE
3734-33-6
Bitrex
Denatonium (benzoate)
Lidocaine benzyl benzoate
THS-839
Anispray
Aversion
Gori
Caswell No. 083BB
UNII-M5BA6GAF1O
Denatonium benzoate anhydrous
WIN 16568
Denatonii benzoas [INN-Latin]
EINECS 223-095-2
Benzoate de denatonium [INN-French]
Benzoato de denatonio [INN-Spanish]
MFCD00031578
M5BA6GAF1O
Denatonium benzoate [USAN:INN:BAN]
EPA Pesticide Chemical Code 009106
NSC 157658
Denatonium benzoate granules
3734-33-6 (benzoate)
C28H34N2O3
Benzyldiethyl((2,6-xylylcarbamoyl)methyl)ammonium benzoate
Benzyldiethyl[(2,6-xylylcarbamoyl)methyl]ammonium benzoate
NCGC00017043-02
CAS-3734-33-6
benzyl-[2-(2,6-dimethylanilino)-2-oxoethyl]-diethylazanium;benzoate
Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate
DSSTox_CID_14376
DSSTox_RID_79149
DSSTox_GSID_34376
((2,6-Xylylcarbamoyl)methyl)diethyl benzyl ammonium benzoate
Ammonium, benzyldiethyl((2,6-xylylcarbamoyl)methyl)-, benzoate
Benzyldiethyl[(2,6-dimethylphenylcarbamoyl)methyl]ammonium Benzoate
Denatonii benzoas
Benzenemethanaminium,N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate
N-(2-((2,6-Dimethylphenyl)amino)-2-oxoethyl)-N,N-diethylbenzeneme- thanaminium benzoate
N-benzyl-2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzoate
Benzoato de denatonio
Benzoate de denatonium
2-[diethylbenzylamino]-N-(2,6-dimethylphenyl)acetamide, benzoic acid
Benzenemethanaminium, N-(2-((2,6-dimethylphenyl)amino)-2-oxoethyl)-N,N-diethyl-, benzoate (1:1)
Benzenemethanaminium, N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate (1:1)
Denatonium Benzoate,99%
SCHEMBL49511
MLS002154073
Denatonium benzoate, >=98%
CHEMBL1371493
Denatonium Benzoate 25% in EG
DTXSID8034376
Denatonium benzoate 3734-33-6
HMS1571A03
HMS2093L12
HMS2098A03
HMS2233O05
HMS3373C04
HMS3715A03
Pharmakon1600-01505987
EBD28935
HY-B1146
KS-000001ET
Tox21_110754
Tox21_301587
NSC157658
NSC759299
SBB057812
AKOS015888129
Tox21_110754_1
CCG-213592
CS-4750
MCULE-8272134756
NSC-157658
NSC-759299
Denatonium benzoate, analytical standard
NCGC00017043-01
NCGC00091886-04
NCGC00164432-01
NCGC00255373-01
AC-14888
AK161798
AS-15511
LS-16789
P665
SC-13384
SMR001233385
SY075333
DB-049095
Ammonium,6-xylylcarbamoyl)methyl]-, benzoate
D2124
FT-0622841
ST51007042
K-8241
A823606
Q414815
W-106547
BENZYLDIETHYL [(2,6-XYLYLCARBAMOYL)-AMMONIUM BENZO
Denatonium benzoate, certified reference material, TraceCERT(R)
benzyl-[(2,6-dimethylphenyl)carbamoylmethyl]-diethyl-azanium benzoate
Benzyl-[(2,6-dimethylphenylcarbamoyl)-methyl]diethylammonium benzoate
Benzyl-[(2,6-dimethylphenylcarbamoyl)methyl]-diethylammonium benzoate
Denatonium benzoate, United States Pharmacopeia (USP) Reference Standard
[2-(2,6-dimethylanilino)-2-oxoethyl]-diethyl-(phenylmethyl)ammonium benzoate
Benzenemethanaminium,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-, benzoate
N-benzyl-2-(2,6-dimethylphenylamino)-N,N-diethyl-2-oxoethanaminium benzoate
[2-[(2,6-dimethylphenyl)amino]-2-oxidanylidene-ethyl]-diethyl-(phenylmethyl)azanium benzoate
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
PubChem