| Identification | More | [Name]
Denatonium benzoate | [CAS]
3734-33-6 | [Synonyms]
AMMONIUM, BENZYLDIETHYL((2,6-XYLYCARBAMOYL)METHYL), BENZOATE
BENZYL-[(2,6-DIMETHYLPHENYLCARBAMOYL)METHYL]DIETHYLAMMONIUM BENZOATE
BENZYLDIETHYL[(2,6-DIMETHYLPHENYLCARBAMOYL)METHYL]AMMONIUM BENZOATE
BENZYLDIETHYL [(2,6-XYLYLCARBAMOYL)-AMMONIUM] BENZOATE
benzyldiethyl(2,6-xylylcarbamoylmethyl)ammonium benzoate
BITREX
BITREX(R)
BITREX (TM)
DENATONIUM BENZOATE
LABOTEST-BB LT00453200
N-[2-[(2,6-Dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-benzenemethanaminium benzoate
N,N-DIETHYL-N-[(2,6-DIMETHYLPHENYLCAR-BAMOYL)METHYL]BENZYLAMMONIUM BENZOATE
REJEXIT (R)
,benzoate
Benzenemethanaminium,N-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-N,N-diethyl-,benzoate
benzyldiethyl((2,6-xylylcarbamoyl)methyl)-ammoniubenzoate
denatonium
denatoniumbenzoate,anhydrous
n-[2-[(2,6-dimethylphenyl)amino]-2-oxoethyl]-n,n-diethyl-benzenemethanaminiu
ths-839 | [EINECS(EC#)]
223-095-2 | [Molecular Formula]
C28H34N2O3 | [MDL Number]
MFCD00031578 | [Molecular Weight]
446.58 | [MOL File]
3734-33-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals | [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) | [Fp ]
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 | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
42.555g/L at 25℃ | [Merck ]
2891 | [BRN ]
8179408 | [InChIKey]
VWTINHYPRWEBQY-UHFFFAOYSA-N | [LogP]
2.2 at 25℃ | [CAS DataBase Reference]
3734-33-6(CAS DataBase Reference) | [EPA Substance Registry System]
3734-33-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
2
| [RTECS ]
BO6650000
| [TSCA ]
Yes | [HS Code ]
29242995 |
| Hazard Information | Back Directory | [Chemical Properties]
Denatonium benzoate occurs as an odorless, very bitter tasting, white crystalline powder or granules. | [Chemical Properties]
white crystals | [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). | [General Description]
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO 17034. This CRM is traceable to primary material from an NMI, e.g. NIST or NMIJ.
Certified content by quantitative NMR incl. uncertainty and expiry date are given on the certificate.
Download your certificate at: http://www.sigma-aldrich.com. | [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
| [Synthesis]
A method for synthesizing Denatonium Benzoate comprises the following steps: (1) adding benzyl halide to a reactor containing raw material lidocaine under stirring and at a certain temperature, wherein the reaction temperature is from room temperature to 130°C, and the ratio of lidocaine to benzyl halide is 1:1 to 1:2; (2) after the reaction is complete, adding solvent and metal hydroxide; (3) adding benzoic acid, after the reaction is completed, the generated benzyl ammonium benzoate is filtered, washed, concentrated, and washed to obtain the product benzyl ammonium benzoate.
| [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). |
| Questions And Answer | Back Directory | [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]
Flavoring agent.
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