6098. S-Methylmethionine

Nomenclature

CAS number: 4727-40-6
[(3S)-3-Amino-3-carboxypropyl]dimethyl sulfonium inner salt; S-methyl-l-methionine; MeMet; vitamin U.
C6H13NO2S; mol wt 163.24.
C 44.15%, H 8.03%, N 8.58%, O 19.60%, S 19.64%.

Description and 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.

Chemical structure

Derivative

Bromide.

Nomenclature

CAS number: 33515-32-1
Methylmethioninesulfonium bromide.
C6H14BrNO2S; mol wt 244.15.
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).

Derivative

dl-Form chloride.

Nomenclature

CAS number: 3493-12-7; 1115-84-0 (l-form chloride)
Methylmethioninesulfonium chloride; MMSC; Cabagin-U (Kowa); Vitas-U (Kaken).
C6H14ClNO2S; mol wt 199.70.
C 36.09%, H 7.07%, Cl 17.75%, N 7.01%, O 16.02%, S 16.06%.

Description and 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.

Therapeutic Category

Antiulcerative.

Keywords

Antiulcerative