Denatonium benzoate

Structural formula
General
Surname	Denatonium benzoate
other names	N -Benzyl-2 - [(2,6-dimethylphenyl) amino] - N , N -diethyl-2-oxoethanaminium benzoate ( IUPAC ) Benzyl diethyl (2,6-xylylcarbamoyl) methylammonium benzoate Bitrex ® Aversion ®
Molecular formula	C 21 H 29 N 2 O • C 7 H 5 O 2
Brief description	white, odorless powder
External identifiers / databases
CAS number 3734-33-6 EC number 223-095-2 ECHA InfoCard 100.020.996 PubChem 19518 ChemSpider 18392 Wikidata Q414815
properties
Molar mass	446.58 g mol −1
Physical state	firmly
Melting point	163-170 ° C
solubility	soluble in water (45 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-332 P: ?
Toxicological data	584 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Denatonium , available as denatonium benzoate or denatonium saccharinate , is the most bitter known substance ( bitter substance ). Denatonium was discovered in 1958 by the Scottish chemist JR Smith while searching for active ingredients for local anesthesia.

Structure and properties

Denatonium is a quaternary ammonium compound and a derivative of the local anesthetic lidocaine , which with a benzyl group to the amine - nitrogen quaternized was. Benzoic acid or saccharin is often used as the anion .

Solution concentrations of 10 ppm have an unbearable bitter taste for humans . The salts of Denatonium are usually colorless and odorless, but are usually only offered as solutions in the trade.

synthesis

The synthesis from lidocaine takes place by reaction with benzyl bromide and subsequent precipitation with benzoic acid .

Applications

The bitter taste of denatonium benzoate is decisive for its areas of application. It is used to ferment ethanol so that the alcohol is no longer suitable for human consumption. This enables an exemption from the spirits tax to be achieved. Other alcohols can also be mixed with Denatonium to health damage caused by accidental or intentional enjoyment to inhibit the uptake of methanol may otherwise z. B. lead to blindness.

Denatonium is used to prevent young children from accidentally swallowing harmful liquids. Denatonium is used in solvents, cleaning agents, shampoos , soaps , game modules for the Nintendo Switch game console and in nail polish to prevent fingernail biting.

There is no knowledge of long-term health risks.

Denatonium works differently in some animals than it does in humans. It can be assumed that rats hardly notice the bitter substance in the usual concentrations. Therefore, for safety reasons, denatonium can also be added to rat poison and thus protects people and other animals from accidental ingestion of the poison. However, there are also cats that have been seen eating the poison bait. It is suspected that they have a genetic defect that also prevented them from perceiving the bitter substance. On the other hand, it is used as a bite protection for wooden fences in horse and cattle husbandry.

Individual evidence

1. ↑ ^{a b c d} Entry on denatonium benzoate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
2. ↑ Entry on denatonium benzoate in the ChemIDplus database of the United States National Library of Medicine (NLM)
3. ^ ^{A b} Arnold Willmes: Pocket book chemical substances , Verlag Harri Deutsch, 2007, ISBN 978-3-8171-1787-1 , p. 8 ( limited preview in Google book search).
4. ↑ ^{a b} Klaus Roth : Chemical delicacies. ISBN 978-3-527-31984-8 .
5. ↑ http://www.polygon.com/2017/3/1/14784140/nintendo-switch-cartridges-taste-awful-psa