3734-33-6 Usage
The 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
Different sources of media describe the Uses of 3734-33-6 differently. You can refer to the following data:
1. Flavoring agent.
2. H1 antihistamine
3. 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.
4. The bitterest compound knownDenatonium benzoate is used as an alcohol denaturant and flavor in pharmaceuticals. It is also used in antifreeze, nail biting preventions, respirator mask fit-testing, animal repellents, liquid soaps and shampoos. Further, it is used in air care products. It acts as H1 antihistamine. In addition to this, it is used as a disinfectant.
Chemical Properties
Different sources of media describe the Chemical Properties of 3734-33-6 differently. You can refer to the following data:
1. white crystals
2. Denatonium benzoate occurs as an odorless, very bitter tasting, white crystalline powder or granules.
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).
Flammability and Explosibility
Notclassified
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,therehasbeenasinglereportof 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).
Check Digit Verification of cas no
The CAS Registry Mumber 3734-33-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,7,3 and 4 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3734-33:
(6*3)+(5*7)+(4*3)+(3*4)+(2*3)+(1*3)=86
86 % 10 = 6
So 3734-33-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H28N2O.C7H6O2.H2O/c1-5-23(6-2,15-19-13-8-7-9-14-19)16-20(24)22-21-17(3)11-10-12-18(21)4;8-7(9)6-4-2-1-3-5-6;/h7-14H,5-6,15-16H2,1-4H3;1-5H,(H,8,9);1H2
3734-33-6Relevant articles and documents
PREPARATION OF A QUATERNARY AMMONIUM HYDROXIDE AND USE THEREOF FOR THE PREPARATION OF Q QUATERNARY AMMONIUM SALT
-
Page/Page column 7-8, (2008/06/13)
The invention relates to a process for the preparation of a quaternary ammonium hydroxide, in particular denatonium hydroxide, and the use thereof for the preparation of a quaternary ammo nium salt, in particular of denatonium benzoate or a denatonium fatty acid derivative. Due to its extremely bitter taste, this latter compound is applied in the art as an aversive agent, biocide, antifoulant and flavorant. It is usually prepared from a quaternary ammonium halide in an organic environment, which after isolation and purification is converted to a hygroscopic and unstable hydroxide intermediate, which in turn is immediately converted to the salt of interest in the solvent in which it is prepared. It is now found that these isolation steps can be avoided by performing the reaction at aqueous conditions. This is more straightforwardly and does not require costly precaut ions to avoid contact while handling. Moreover, the process of the invention allows to produce the quaternary ammonium salt from a lignocaine compound in a one-pot synthesis involving mostly water.