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Encyclopedia > Denatonium
Denatonium benzoate
Chemical structure of Denatonium Chemical structure of benzoate
Systematic name N-benzyl-2-(2,6-dimethylphenylamino)-
N,N-diethyl-2-oxoethanaminium benzoate
Chemical formula C21H29N2O·C7H5O2
Molecular mass 446.58 g/mol
Density x.xxx g/cm³
Melting point 166-170 °C
Boiling point xx.x °C
CAS number [3734-33-6]
SMILES S=CC1=CC=CC(C)=C1NC(C[N+](CC)(CC)
CC2=CC=CC=C2)=O.O=C([O-])C3=CC=CC=C3
Disclaimer and references

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. Image File history File links Denatonium_chemical_structure. ... Image File history File links Denatonium_benzoate_chemical_structure_part_2. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... Density, or volumic mass (ISO 31), is a measure of mass per volume. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A trade name, also known as a trading name or a business name, is the legal name of a business, or the name which a business trades under for commercial purposes. ... The basic tastes are the commonly recognized types of taste sensed by humans. ... A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... A local anesthetic is a drug that reversibly inhibits the propagation of signals along nerves. ... Edinburgh (pronounced ; Scottish Gaelic: ) is the capital of Scotland and its second-largest city. ... Motto: (Latin for No one provokes me with impunity)1 Anthem: Multiple unofficial anthems Capital Edinburgh Largest city Glasgow Official language(s) English, Gaelic, Scots 2 Government Constitutional monarchy  - Queen Queen Elizabeth II  - Prime Minister of the UK Tony Blair MP  - First Minister Jack McConnell MSP Unification    - by Kenneth I... The parts-per notations are used to denote extremely low concentrations of chemical elements. ... // For eat or EAT as an abbreviation or acronym, see EAT. In general terms, eating (formally, ingestion) is the process of consuming ghosts, i. ... PRAY TO THE GREAT METHYLATED SPIRIT ... A man pouring antifreeze into his vehicle. ... Nails of a nail bitter. ... Animal Repellants are products designed to keep animals away from objects. ... Handmade soap Soap is a surfactant used in conjunction with water for washing and cleaning. ... Several shampoos on a shower window Shampoo (Hindi: शम्पू) is a hair care product used for the removal of oils, dirt, skin particles, environmental pollution and/or other contaminant particles that gradually build up in hair. ...


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. Categories: Chemistry stubs ... A magnified crystal of a salt (halite/sodium chloride) Salt covering the floor of Bad Water in Death Valley, CA, the lowest point in the US. A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral... In English, to be inert is to be in a state of doing little or nothing. ... Multivalent redirects here. ... The benzoate ion is C6H5COO− (benzoic acid minus one hydrogen ion). ... an essential structural component of living cells and source of energy for animals; includes simple sugars with small molecules as well as macromolecular substances; are classified according to the number of monosaccharide groups they contain. ... A local anesthetic is a drug that reversibly inhibits the propagation of signals along nerves. ... Lidocaine (INN) (IPA: ) or lignocaine (former BAN) (IPA: ) is a common local anesthetic and antiarrhythmic drug. ... Benzyl is the Organic chemistry term for the radical C6H5CH2-. It is obtained by removing a proton from benzene. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ...


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. Denatured alcohol is ethanol with added adulterants that make it useless for consumption as an intoxicating beverage by rendering it toxic or extremely distasteful to drink, but still useful for industrial processes or as a household chemical. ... Bottles of cachaça, a Brazilian alcoholic beverage. ...


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. Functional group of an alcohol molecule. ... Methanol, also known as methyl alcohol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ... For other uses, see Solvent (disambiguation). ... This article does not cite its references or sources. ... Varnish is a transparent, hard, protective finish or film primarily used in wood finishing but also for other materials. ...


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. Official language(s) None Capital Salem Largest city Portland Area  Ranked 9th  - Total 98,466 sq mi (255,026 km²)  - Width 260 miles (420 km)  - Length 360 miles (580 km)  - % water 2. ... Ethylene glycol (monoethylene glycol (MEG), IUPAC name: ethane-1,2-diol) is an alcohol with two -OH groups (a diol), a chemical compound widely used as an automotive antifreeze. ... Methanol, also known as methyl alcohol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ...


Other uses include nail polish for preventing nail biting, and as animal repellent (especially for big game like deer). Game is any animal hunted for food or not normally domesticated (such as venison). ... Fawn redirects here. ...


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.[citation needed] 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. A rat in urban environment Rat poisons are a category of pest control chemicals intended to kill rats. ... Trinomial name Felis silvestris catus (Linnaeus, 1758) The cat (or domestic cat, house cat) is a small carnivorous mammal. ... For a non-technical introduction to the topic, please see Introduction to genetics. ... Phenylthiocarbamide, also known as PTC, or phenylthiourea, is a synthetic organic molecule. ...


External links

  • Links to external chemical sources

  Results from FactBites:
 
Denatonium - Wikipedia, the free encyclopedia (455 words)
Denatonium is used in denatured alcohol, antifreeze, nail biting preventions, animal repellents, liquid soaps, and shampoos.
The structure of denatonium is related to the local anesthetic lidocaine, differing only by the addition of a benzyl group to the amino nitrogen.
Denatonium is used to denature ethanol so that it is not taxed as an alcoholic beverage.
  More results at FactBites »

 
 

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