Denatonium

Denatonium benzoate
Denatonium benzoate crystals
Skeletal formula of the denatonium cation
Skeletal formula of the benzoate anion
Ball-and-stick models of the both ions in denatonium benzoate
Names
Preferred IUPAC name
N-Benzyl-2-(2,6-dimethylanilino)-N,N-diethyl-2-oxoethan-1-aminium benzoate
Other names
N-Benzyl-2-[(2,6-dimethylphenyl)amino]-N,N-diethyl-2-oxoethan-1-aminium benzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.996 Edit this at Wikidata
EC Number
  • 223-095-2
UNII
  • InChI=1S/C21H28N2O.C7H6O2/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) checkY
    Key: VWTINHYPRWEBQY-UHFFFAOYSA-N checkY
  • InChI=1/C21H28N2O.C7H6O2/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)
    Key: VWTINHYPRWEBQY-UHFFFAOYAY
  • [O-]C(=O)c1ccccc1.Cc2cccc(C)c2NC(=O)C[N+](CC)(CC)Cc3ccccc3
Properties
C28H34N2O3
Molar mass 446.581
Appearance white crystalline
Melting point 163 to 170 °C (325 to 338 °F; 436 to 443 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H315, H318, H332, H412
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Denatonium, usually available as denatonium benzoate (under trade names such as Denatrol, BITTERANT-b, BITTER+PLUS, Bitrex, Bitrix, and Aversion) and as denatonium saccharide (BITTERANT-s), is the most bitter chemical compound known, with bitterness thresholds of 0.05 ppm for the benzoate and 0.01 ppm for the saccharide.[1] It was discovered in 1958 during research on local anesthetics by T. & H. Smith of Edinburgh, Scotland, and registered under the trademark Bitrex.[2][3]

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 (bitterants) to prevent inappropriate ingestion. Denatonium is used in denatured alcohol,[4] antifreeze, preventive nail biting preparations, respirator mask fit-testing, animal repellents, liquid soaps, shampoos, and Nintendo Switch game cards to prevent accidental swallowing or choking by children. It is not known to pose any long-term health risks.[1]

The name denatonium reflects the substance's primary use as a denaturant and its chemical nature as a cation, hence -onium as a Neo-Latin suffix.

  1. ^ a b Final Report Study of Aversive Agents (PDF). Consumer Product Safety Commission United States of America. 18 November 1992. Archived from the original (PDF) on 16 June 2011. Retrieved 15 November 2010.
  2. ^ "Bitrex(R) — Branded Denatonium Benzoate". Macfarlan Smith. Archived from the original on 2010-08-17. Retrieved 2010-05-09.
  3. ^ "Denatonium Benzoate". Encyclopedia.com. Retrieved 30 August 2024.
  4. ^ "Ethanol Denaturants". The Online Distillery Network. 1993-11-22. Archived from the original on 2015-05-10. Retrieved 2007-09-30.