1115-84-0 Usage
Chemical Properties
Naturally occurs as the L-form in a variety of vegetables. Although used in food as a flavoring ingredient in fish products, it has also been used therapeutically in the treatment of peptic ulcers, colitis and gastritis.
Originator
Cabagin-U,Kowa
Occurrence
Reported found in asparagus, cabbage, cabbage juice, celery, sweet corn, milk, potato, tea, green tea and
tomato.
Uses
A derivative of L-Methionine (M260440). Naturally occurring sulfonium compound found in a large number of plants. Identification of antiulcer vitamin in cabbage leaves. Antiulcerative.
Manufacturing Process
298 g dl-methionine, 2000 ml water and 151.1 methyl chloride were put into autoclave (volume 3 L) made from V4-a steel. The mixture was heated at temperature 50°-55°C for 8 hours and pressure 12-13 atmospheres. On cooling an excess of methyl chloride was evaporated, the slightly yellow residue was mixed with 0.2% activated coal and filtered. Water was evaporated in vacuum at 45°-55°C. 2 L methanol was poured into an almost colorless syrup obtained, cooled to -5°-(-10°)C. The methylmethioninesulfonium chloride crystallized. It was filtered off to give 340 g (85.3%) of desired product 99.5 % purity (data of thin-layer chromatography).
Therapeutic Function
Hepatoprotectant
Taste threshold values
Taste characteristics at 5 ppm: sulfureous creamy, tomato, malty, vegetable like
Purification Methods
Likely impurities are methionine, methionine sulfoxide and methionine sulfone. Crystallise Vitamin U from water by adding a large excess of EtOH. It is hygroscopic. It should be stored in a cool, dry place and protected from light. It has also been purified on a column of Dowex 50 H+ form, washed with H2O and eluted with 6N ammonia, lyophilised, the residue is dissolved in dilute HCl, lyophilised again and then it is obtained as colourless prisms by vapour diffusion of Et2O in a 1:1 (v/v) mixture of MeOH/EtOH in which the hydrochloride is dissolved [Del Re Acta Cryst B 33 3289 1977]. The iodide salt, m ~ 150o(dec), is obtained by dissolving it in 50% aqueous EtOH and adding ~3.5 volumes of absolute EtOH. The bromide salt has m 140o(dec) [Toennies & Kolb J Amer Chem Soc 67 849 1945].
Check Digit Verification of cas no
The CAS Registry Mumber 1115-84-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 5 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1115-84:
(6*1)+(5*1)+(4*1)+(3*5)+(2*8)+(1*4)=50
50 % 10 = 0
So 1115-84-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO2S.ClH/c1-10(2)4-3-5(7)6(8)9;/h5H,3-4,7H2,1-2H3;1H/t5-;/m0./s1
1115-84-0Relevant articles and documents
Double-headed sulfur-linked amino acids as first inhibitors for betaine-homocysteine S -methyltransferase 2
Mládková, Jana,Vaněk, Václav,Budě?ínsky, Milo?,Elbert, Tomá?,Demianová, Zuzana,Garrow, Timothy A.,Jirá?ek, Ji?í
experimental part, p. 6822 - 6831 (2012/10/07)
Betaine-homocysteine S-methyltransferase 2 (BHMT-2) catalyzes the transfer of a methyl group from S-methylmethionine to l-homocysteine, yielding two molecules of l-methionine. It is one of three homocysteine methyltransferases in mammals, but its overall contribution to homocysteine remethylation and sulfur amino acid homeostasis is not known. Moreover, recombinant BHMT-2 is highly unstable, which has slowed research on its structural and catalytic properties. In this study, we have prepared the first series of BHMT-2 inhibitors to be described, and we have tested them with human recombinant BHMT-2 that has been stabilized by copurification with human recombinant BHMT. Among the compounds synthesized, (2S,8RS,11RS)-5-thia-2,11-diamino-8-methyldodecanedioic acid (11) was the most potent (Kiapp ～77 nM) and selective inhibitor of BHMT-2. Compound 11 only weakly inhibited human BHMT (IC 50 about 77 μM). This compound (11) may be useful in future in vivo studies to probe the physiological significance of BHMT-2 in sulfur amino acid metabolism.
