S-Methylmethionine
Title: S-Methylmethionine
CAS Registry Number: 4727-40-6
CAS Name: [(3S)-3-Amino-3-carboxypropyl]dimethyl sulfonium inner salt
Additional Names: S-methyl-L-methionine; MeMet; vitamin U
Molecular Formula: C6H13NO2S
Molecular Weight: 163.24
Percent Composition: C 44.15%, H 8.03%, N 8.58%, O 19.60%, S 19.64%
Literature References: Naturally occurring sulfonium compound found in a large number of plants. Identification of antiulcer vitamin in cabbage leaves: G. Cheney, Calif. Med. 77, 248 (1952). Isoln from cabbage juice: R. A. McRorie et al., J. Am. Chem. Soc. 76, 115 (1954). Activity: V. Z. Szabo, G. Vargha, Arzneim.-Forsch. 10, 23 (1960). Determn in plant tissue: P. K. Macnicol, Anal. Biochem. 158, 93 (1986). Review of biosynthesis and physiological role in plants: J. Giovanelli et al., "Sulfur Amino Acids in Plants " in The Biochemistry of Plants 5, B. J. Miflin, Ed. (Academic Press, New York, 1980) pp 453-505.
 
Derivative Type: Bromide
CAS Registry Number: 33515-32-1
Additional Names: Methylmethioninesulfonium bromide
Molecular Formula: C6H14BrNO2S
Molecular Weight: 244.15
Percent Composition: C 29.52%, H 5.78%, Br 32.73%, N 5.74%, O 13.11%, S 13.13%
Properties: White platelets from ethanol, mp 139° (dec).
Melting point: mp 139° (dec)
 
Derivative Type: DL-Form chloride
CAS Registry Number: 3493-12-7; 1115-84-0 (L-form chloride)
Additional Names: Methylmethioninesulfonium chloride; MMSC
Trademarks: Cabagin-U (Kowa); Vitas-U (Kaken)
Molecular Formula: C6H14ClNO2S
Molecular Weight: 199.70
Percent Composition: C 36.09%, H 7.07%, Cl 17.75%, N 7.01%, O 16.02%, S 16.06%
Literature References: Prepn: R. O. Atkinson, F. Poppelsdorf, J. Chem. Soc. 1951, 1378. HPLC determn in pharmaceutical prepns: C. P. Leung, W. K. H. Leung, J. Chromatogr. 479, 361 (1989). Clinical evaluation in ulcerative colitis: A. S. Salim, Pharmacology 45, 307 (1992).
Properties: Crystals from hot ethanol, mp 134° (dec). Very hygroscopic; hydrolysed rapidly in alkaline media.
Melting point: mp 134° (dec)
 
Therap-Cat: Antiulcerative.
Keywords: Antiulcerative.

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