1179. Betaine

Nomenclature

CAS number: 107-43-7
1-Carboxy-N,N,N-trimethylmethanaminium inner salt; (carboxymethyl)trimethylammonium hydroxide inner salt; glycine betaine; glycocoll betaine; lycine; oxyneurine; trimethylglycine hydroxide inner salt; trimethylglycocoll anhydride; Cystadane (Orphan Med.).
C5H11NO2; mol wt 117.15.
C 51.26%, H 9.46%, N 11.96%, O 27.31%.

Description and references

Widely distributed in plants and animals: M. Guggenheim, Die biogenen Amine (S. Karger, Basel, 4th ed., 1951) pp 240-242. Prepn via or from hydrochloride: Stoltzenberg, Z. Physiol. Chem. 92, 445 (1914); Edsall, J. Am. Chem. Soc. 65, 1767 (1943). Prepn of the hydrochloride: Kuhn, Ruelius, Ber. 83, 420 (1950); of the hydrate: Vassel, US 2800502 (1957 to IMC). Structure of hydrate: Leifer, Lippincott, J. Am. Chem. Soc. 79, 5098 (1957). HPLC determn in urine: M. D. Laryea et al., Clin. Chim. Acta 230, 169 (1994). Clinical evaluations in homocystinuria: D. E. Wilcken et al., N. Engl. J. Med. 309, 448 (1983); N. P. B. Dudman et al., J. Nutr. 126, Suppl. 4, 1295S (1996).

Chemical structure

Properties

Deliquescent scales or prisms dec around 310°. (Isomerizes at the mp to methyl ester of dimethylaminoacetic acid.) Sweet taste. Solubility (g/100 g solvent): water, 160; methanol, 55; ethanol, 8.7. Sparingly sol in ether. Betaine yields trimethylamine with concd KOH.

Derivative

Monohydrate.

Nomenclature

CAS number: 590-47-6
(Carboxymethyl)trimethylammonium hydroxide; trimethylglycine hydroxide.

Properties

Formed by crystn of betaine from aq solvents. pH of satd soln about 8.0. Loses water at 100° forming inner salt again.

Derivative

Hydrochloride.

Nomenclature

CAS number: 590-46-5
1-Carboxy-N,N,N-trimethylmethanaminium chloride; (carboxymethyl)trimethylammonium chloride; pluchine; Acidol (Bayer).
C5H11NO2.HCl; mol wt 153.61.
C 39.09%, H 7.87%, N 9.12%, O 20.83%, Cl 23.08%.

Properties

Monoclinic crystals from alc, dec 227-228° (Stoltzenberg); also reported as dec 232° (Kuhn, Ruelius). Soly in water at 25° = 64.7 g/100 ml, in ethanol 5.0 g/100 ml. pH of 5% aq soln 1.0. Practically insol in chloroform, ether.

Derivative

Sodium aspartate.

Nomenclature

CAS number: 93227-64-6
Somatyl (Teofarma).
C9H17N2NaO6; mol wt 272.23.
C 39.71%, H 6.29%, N 10.29%, Na 8.44%, O 35.26%.

Description and references

Prepn: R. Cote, FR 1356945 (1964), C.A. 61, 7098 (1964).

Properties

Prepd as trihydate, dec 160-170°. Hygroscopic. Sol in water.

Use

In soldering, resin curing fluxes, organic synthesis.

Therapeutic Category

In treatment of homocystinuria; hepatoprotectant. Hydrochloride as gastric acidifier.

Keywords

Hepatoprotectant

Betaine Hydrochloride: Acidifier