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Properties of substance:

denatonium saccharinate



skc-file

Group of substances:

organic

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

C28H33N3O4S

Molar/atomic mass: 507.64

Melting point (°C):

177

Solubility (g/100 g of solvent):

2-propanol: soluble [Ref.]
acetone: moderately soluble (50°C) [Ref.]
acetonitrile: moderately soluble (50°C) [Ref.]
chloroform: soluble [Ref.]
dimethylsulfoxide: soluble [Ref.]
ethyl acetate: moderately soluble (50°C) [Ref.]
hexane: insoluble [Ref.]
methanol: soluble [Ref.]
toluene: insoluble [Ref.]
water: 0.1 [Ref.]

Numerical data:

Bitter taste threshold concentrations (mM): 2.0E-5
Bitter taste threshold concentrations (%): 1.0E-6

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. 1606-1607, S15 [doi: 10.1021/acs.jchemed.1c00995]

According to elaborated procedure, mix 2 ml of commercial ethanol with 0.70 g (1.94 mmol) of denatonium chloride and 0.46 g (1.94 mmol) of sodium saccharinate dihydrate. Then, stir the content of the flask for 10 minutes at 50°Ñ. As the result, sodium chloride as a by-product should precipitate from solution. Next, cool the post-reaction mixture to 4°C, filtrate the sediment and wash it with 1 ml of ethanol. The obtained filtrate should be evaporated under reduced pressure and a white solid, characterized by melting point of 176.0—178.5°C, should be obtained with a 99% yield (0.97 g).

LD50 (mg/kg):

1430 (rats, oral)

References:

  1. Ïàòåíò ÑØÀ US4,652,577 (îò 24.03.1987)
  2. Ïàòåíò ÑØÀ US4,661,504 (îò 28.04.1987)

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    © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru