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Denatonium Benzoate

The most bitter compound in the world Chemical structure Uses

Denatonium Benzoate

CAS No.3734-33-6
Chemical Name:Denatonium Benzoate
CBNumber:CB2674421
Molecular Formula:C28H34N2O3
Formula Weight:446.58
MOL File:3734-33-6.mol

Denatonium Benzoate Property

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)
Flash point 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
Water Solubility 42.555g/L at 25℃
Merck 14,2891
BRN 8179408
Stability Stable. Incompatible with strong oxidizing agents.
InChIKey VWTINHYPRWEBQY-UHFFFAOYSA-N
LogP 2.2 at 25℃
CAS DataBase Reference 3734-33-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII M5BA6GAF1O
EPA Substance Registry System Denatonium benzoate (3734-33-6)
UNSPSC Code 41116107
NACRES NA.24

Safety

Hazard Codes :Xn,Xi
Risk Statements :22-36/37/38-20/21/22
Safety Statements :26-36-37/39
WGK Germany :2
RTECS :BO6650000
TSCA :Yes
HS Code :29242995

NFPA 704:

	0
4		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H412
Precautionary statements P264-P270-P273-P301+P312-P501

Denatonium Benzoate Price More Price(14)

Brand: Sigma-Aldrich(India)
Product number: D5765
Product name : Denatonium benzoate
Purity: ≥98%
Packaging: 1G
Price: ₹4968.68
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D5765
Product name : Denatonium benzoate
Purity: ≥98%
Packaging: 5G
Price: ₹12210.6
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: D5765
Product name : Denatonium benzoate
Purity: ≥98%
Packaging: 10G
Price: ₹22949
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 93675
Product name : Denatonium benzoate
Purity: certified reference material, TraceCERT?
Packaging: 100MG
Price: ₹8616.7
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 52487
Product name : Denatonium benzoate
Purity: PESTANAL?, analytical standard
Packaging: 100MG
Price: ₹6603.25
Updated: 2022/06/14
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Denatonium Benzoate Chemical Properties,Usage,Production

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.
Chemical Properties Denatonium benzoate occurs as an odorless, very bitter tasting, white crystalline powder or granules.
Chemical Properties white crystals
Uses 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.
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).
Flammability and Explosibility Not classified
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).