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Properties of substance:

denatonium chloride

Group of substances:

organic

Empirical formula (Hill's system for organic substances):

C21H29ClN2O

Structural formula as text:

[(CH3)2C6H3NHCOCH2N(C2H5)2CH2C6H5]Cl

Molar/atomic mass: 360.9208

Solubility (g/100 g of solvent):

2-propanol: moderately soluble [Ref.]
acetone: insoluble [Ref.]
acetonitrile: moderately soluble (50°C) [Ref.]
chloroform: soluble [Ref.]
dimethylsulfoxide: moderately soluble [Ref.]
ethyl acetate: insoluble [Ref.]
hexane: insoluble [Ref.]
methanol: soluble [Ref.]
toluene: insoluble [Ref.]
water: soluble [Ref.]

Numerical data:

Bitter taste threshold concentrations (mM): 1.0E-5-2.0E-5

Synthesis 1:

Reference: Stachowiak W., Wysocki M., Niemczak M. “Bitter” Results: Toward Sustainable Synthesis of the Most Bitter Substances, Denatonium Saccharinate and Denatonium Benzoate, Starting from a Popular Anesthetic, Lidocaine / Journal of Chemical Education. - 2022. - Vol. 99, No. 4 pp. 1606, S12 [doi: 10.1021/acs.jchemed.1c00995]


(CH3)2C6H3NHCOCH2N(C2H5)2 + C6H5CH2Cl → (CH3)2C6H3NHCOCH2N(C2H5)2(CH2C6H5)Cl

Time needed: 4 hours

Introduce 3.36 g (14.34 mmol) of lidocaine, 2 ml acetonitrile, 1.88 g (14.85 mmol) of benzyl chloride and 34 mg (0.2 mmol) of potassium iodide into the round-bottom flask. Then mix and heat the content of flask under reflux at 80°Ń. After 2 hours remove the acetonitrile under reduced pressure on a rotary evaporator. In next step crush the raw product to pieces with spatula and mix it with 20 ml of ethyl acetate. Then, separate the obtained mixture using vacuum filtration and wash the solid with second portion (10 ml) of ethyl acetate. Later dry the crude product under vacuum for 1 hour at 80°C. Yield should be in range 4.15—4.65 g (80—90%).

LD50 (mg/kg):

820 (rats, oral)

References:

  1. Saroli A. Interaction of denatonium chloride with the bitter taste receptor / Zeitschrift fur Lebensmittel-Untersuchung und Forschung. - 1985. - Vo. 180, No. 3. - pp. 228

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru