Sarcosine
Title: Sarcosine
CAS Registry Number: 107-97-1
CAS Name: N-Methylglycine
Additional Names: N-methylaminoacetic acid; Sar; N-methylglycocoll; methylaminoethanoic acid
Molecular Formula: C3H7NO2
Molecular Weight: 89.09
Percent Composition: C 40.44%, H 7.92%, N 15.72%, O 35.92%
Line Formula: CH3NHCH2COOH
Literature References: Has been found in starfish and sea urchins: A. Kossel, S. Edlbacher, Z. Physiol. Chem. 94, 264 (1915); in rock lobsters: L. Novellie, H. M. Schwartz, Nature 173, 450 (1954). Formation from caffeine by dec with barium hydroxide: Paulmann, Arch. Pharm. 232, 601 (1894). Prepd on a large scale from formaldehyde, sodium cyanide, and methylamine: Eschweiler, Ann. 279, 39 (1894); Baumann, J. Biol. Chem. 21, 563 (1915); Caverly, US 2720540 (1955 to du Pont); Leake, Brakebill, US 3009954 (1961 to Allied Chem.). Synthesis: M. Ebata et al., Bull. Chem. Soc. Jpn. 39, 2535 (1966). Review of syntheses: T. Shirai, Synthetic Production and Utilization of Amino Acids, T. Kaneko et al., Eds. (Wiley, New York, 1974) pp 184-186.
Properties: Orthorhombic, deliquescent crystals from dil methanol. Dec 212°. Sweetish taste. pK1¢ 2.23; pK2¢ 10.01. Sol in water: 5 ml of a satd aq soln contain 2.1412 g sarcosine. Slightly sol in alc.
pKa: pK1¢ 2.23; pK2¢ 10.01
 
Derivative Type: Sodium salt
Properties: Usually sold as aq soln, pH 12.0.
 
Derivative Type: Hydrochloride
Molecular Formula: C3H7NO2.HCl
Molecular Weight: 125.55
Percent Composition: C 28.70%, H 6.42%, N 11.16%, O 25.49%, Cl 28.24%
Properties: Needles from alcohol, dec 171°. Freely sol in water; slightly sol in alcohol, ether.
 
Use: Intermediate in the synthesis of antienzyme agents for toothpaste.

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