Betaine
Title: Betaine
CAS Registry Number: 107-43-7
CAS Name: 1-Carboxy-N,N,N-trimethylmethanaminium inner salt
Additional Names: (carboxymethyl)trimethylammonium hydroxide inner salt; glycine betaine; glycocoll betaine; lycine; oxyneurine; trimethylglycine hydroxide inner salt; trimethylglycocoll anhydride
Trademarks: Cystadane (Orphan Med.)
Molecular Formula: C5H11NO2
Molecular Weight: 117.15
Percent Composition: C 51.26%, H 9.46%, N 11.96%, O 27.31%
Literature 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).
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 Type: Monohydrate
CAS Registry Number: 590-47-6
Additional Names: (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 Type: Hydrochloride
CAS Registry Number: 590-46-5
CAS Name: 1-Carboxy-N,N,N-trimethylmethanaminium chloride
Additional Names: (carboxymethyl)trimethylammonium chloride; pluchine
Trademarks: Acidol (Bayer)
Molecular Formula: C5H11NO2.HCl
Molecular Weight: 153.61
Percent Composition: 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 Type: Sodium aspartate
CAS Registry Number: 93227-64-6
Trademarks: Somatyl (Teofarma)
Molecular Formula: C9H17N2NaO6
Molecular Weight: 272.23
Percent Composition: C 39.71%, H 6.29%, N 10.29%, Na 8.44%, O 35.26%
Literature 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.
Therap-Cat: In treatment of homocystinuria; hepatoprotectant. Hydrochloride as gastric acidifier.
Keywords: Hepatoprotectant.

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