3493-12-7

Basic information

• Product Name: DL-METHIONINE METHYLSULFONIUM CHLORIDE
• Synonyms: VITAMIN U;VITAMIN U CHLORIDE;(3-amino-3-carboxypropyl)dimethyl-,chloride,(+/-)-sulfoniu;S-METHYL-DL-METHIONINE-SULFONIUMCHLORIDE;S-METHYLMETHIONINESULFONIUM CHLORIDE;METHYL-METHIONINE SULPHONIUM CHLORIDE;DL-METHYLMETHIONINE SULFONIUMCHLORIDE;DL-METHIONINE METHYLSULFONIUM CHLORIDE
• CAS NO: 3493-12-7
• Molecular Formula: C₆H₁₄NO₂S*Cl
• Molecular Weight: 199.7
• EINECS: 222-484-4
• Product Categories: Iodonium Sulfonium & Oxonium Compounds;Sulfonium Compounds;Vitamin series
• Mol File: 3493-12-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 139-140 °C (dec.)
• Appearance: /
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: H2O: soluble100mg/mL, clear, colorless
• Stability: Hygroscopic
• Merck: 14,6098
• BRN: 4163617
• CAS DataBase Reference: DL-METHIONINE METHYLSULFONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-METHIONINE METHYLSULFONIUM CHLORIDE(3493-12-7)
• EPA Substance Registry System: DL-METHIONINE METHYLSULFONIUM CHLORIDE(3493-12-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 3493-12-7(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 3493-12-7 differently. You can refer to the following data:
1. DL-Methionine Methylsulfonium Chloride is a compound comprised of γ-glutamyl peptide and amino acid that have a sucrose-like taste.
2. Vitamin U (DL-methionine methylsulfonium chloride) is a natural methionine-derivative, found as an active component in the methionine cycle of plants where it serves as a substrate for methyl transferases (Augspurger et al., 2005). Historically this compound has been utilized as either a cure or preventative against gastric and duodenal ulcers (Nakamura et al., 1981).

Biochem/physiol Actions

S-Methionine methylsulfonium (SMMS) chloride is a derivative of methionine metabolism in some plants. SMMS has potent therapeutic effects on gastrointestinal ulceration potentially via its ability to promote dermal fibroblast migration and growth.

InChI:InChI=1/C6H13NO2S.ClH/c1-10(2)4-3-5(7)6(8)9;/h5H,3-4,7H2,1-2H3;1H

Synthetic route

DL-methionine-S-methylsulfonium chloride (3493-12-7) + glycine (56-40-6) + zinc(II) oxide → (diaquachloro-S-methylmethioniato)(glycinato)zinc

Conditions	Yield
In water reaction of ZnO with ligands in H2O (equimolar amounts); elem. anal.;	96%

DL-methionine-S-methylsulfonium chloride (3493-12-7) + aspartic Acid (617-45-8) + zinc(II) oxide → (diaquachloro-S-methylmethioninato)(asparaginato)-O,O'-zinc

Conditions	Yield
In ethanol reaction of ZnO with ligands in H2O (equimolar amounts); elem. anal.;	96%

DL-methionine-S-methylsulfonium chloride (3493-12-7) + rac-Ala-OH (302-72-7) + zinc(II) oxide → (aquachloro-S-methylmethioniato)(alaninato)zinc

Conditions	Yield
In water reaction of ZnO with ligands in H2O (equimolar amounts); elem. anal.;	95%

Glutamic acid (617-65-2) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + zinc(II) oxide → (aquachloro-S-methylmethionato)(glutaminato)-O,O'-zinc (132032-38-3)

Conditions	Yield
In water reaction of ZnO with ligands in H2O (equimolar amounts); elem. anal.;	93%

chloride (16887-00-6) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + chloroperoxidase → methyl bromide (74-83-9) + methylene chloride (74-87-3) + methyl iodide (74-88-4)

Conditions	Yield
With sea salt; dihydrogen peroxide; potassium carbonate In phosphate buffer Methylation;

bromide (10097-32-2) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + chloroperoxidase → methyl bromide (74-83-9) + methyl iodide (74-88-4)

Conditions	Yield
With sea salt; dihydrogen peroxide; potassium carbonate In phosphate buffer Methylation;

iodide (14362-44-8) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + chloroperoxidase → methyl bromide (74-83-9) + methyl iodide (74-88-4)

Conditions	Yield
With sea salt; dihydrogen peroxide; potassium carbonate In phosphate buffer Methylation;

DL-methionine-S-methylsulfonium chloride (3493-12-7) → (3-carboxy-3-chloro-propyl)-dimethyl sulfonium + <3-carboxy-3-hydroxy-propyl>-dimethyl sulfonium

Conditions	Yield
With hydrogenchloride; sodium nitrite

cobalt(III) hydroxide + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Co{(CH3)2S(Cl)(CH2)2CH(NH2)COO}3*2H2O

Conditions	Yield
In not given room temp.;

cobalt(III) hydroxide + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Co{(CH3)2S(Cl)(CH2)2CH(NH2)COO}3*4H2O

Conditions	Yield
In not given heating (67-70°C, 3 h);

DL-methionine-S-methylsulfonium chloride (3493-12-7) + cobalt(II) chloride (7646-79-9) → 2(CH3)2S(CH2)2CH(NH3)COO(1+)*CoCl4(2-)={(CH3)2S(CH2)2CH(NH3)COO}2CoCl4 + (CH3)2S(CH2)2CH(NH3)COO(1+)*CoCl3(1-)={(CH3)2S(CH2)2CH(NH3)COO}CoCl3

Conditions	Yield
In acetone

nickel(II) chloride hexahydrate + Glutamic acid (617-65-2) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → {NiCl3(H2O)3}(1-)*(CH3)2SC3H5NH2COOH(1+)*COOHCHNH2C2H4COOH*8H2O={NiCl3(H2O)3}(CH3)2SC3H5NH2COOH(COOHCHNH2C2H4COOH)*8H2O

Conditions	Yield
In ethanol addn. of an equimolar quantity of NiCl2*6H2O to satd. solns. of the ligands in ethanol; purifn. with ethanol, isolation from the mother soln. with acetone, elem. anal.;

copper(II) choride dihydrate + Glutamic acid (617-65-2) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Cu(2+)*2Cl(1-)*HOOCC2H4CH(NH2)COO(1-)*H2O*HO2CCH(NH2)CH2CH2S(CH3)2(1+)={CuCl2(C5H8O4N)(H2O)}{HO2CCH(NH2)CH2CH2S(CH3)2}

Conditions	Yield
In ethanol; water addn. of Cu-salt in EtOH to saturated aq. soln. of ligands, stirred until no further decolourisation of the supernatant liquid; sepn. of the mother-liquor, residue treated two or three times with EtOH and with acetone until the organic solvent gave negative test for Cl(1-), powdered product washed three times with ether; elem. anal.;

nickel(II) carbonate (719261-06-0) + Glutamic acid (617-65-2) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Ni((CH3)2SCH2CH2CH(NH2)COO)(COOCH(NH2)(CH2)2COOH)(H2O)2(1+)*Cl(1-)=Ni((CH3)2S(Cl)C3H5(NH2)COO)(COOCH(NH2)C2H4COOH)*2H2O

Conditions	Yield
In water addn. of basic NiCO3 to equimolar quantities of the ligands dissolved in water; filtration, salting-out by repeated treating with acetone, elem. anal.;

nickel(II) chloride hexahydrate + DL-methionine-S-methylsulfonium chloride (3493-12-7) + glycine (56-40-6) → {NiCl3(H2O)3}(1-)*(CH3)2SCH2CH2CH(NH2)COOH(1+)*CH2(NH2)COOH*2H2O={NiCl3(H2O)3}((CH3)2SC3H5(NH2)COOH)(CH2(NH2)COOH)*2H2O

Conditions	Yield
In ethanol addn. of an equimolar quantity of NiCl2*6H2O to satd. solns. of the ligands in ethanol; purifn. with ethanol, isolation from the mother soln. with acetone, elem. anal.;

nickel(II) chloride hexahydrate + DL-methionine-S-methylsulfonium chloride (3493-12-7) + aspartic Acid (617-45-8) → {NiCl3(H2O)3}(1-)*(CH3)2SC3H5NH2COOH(1+)*COOHCHNH2CH2COOH*5H2O={NiCl3(H2O)3}(CH3)2SC3H5NH2COOH(COOHCHNH2CH2COOH)*5H2O

Conditions	Yield
In ethanol addn. of an equimolar quantity of NiCl2*6H2O to satd. solns. of the ligands in ethanol; purifn. with ethanol, isolation from the mother soln. with acetone, elem. anal.;

nickel(II) chloride hexahydrate + DL-methionine-S-methylsulfonium chloride (3493-12-7) + rac-Ala-OH (302-72-7) → {NiCl3(H2O)3}(1-)*(CH3)2SCH2CH2CH(NH2)COOH(1+)*CH3CH(NH2)COOH*3H2O={NiCl3(H2O)3}(CH3)2SC3H5(NH2)COOH(CH3CHNH2COOH)*3H2O

Conditions	Yield
In ethanol addn. of an equimolar quantity of NiCl2*6H2O to satd. solns. of the ligands in ethanol; purifn. with ethanol, isolation from the mother soln. with acetone, elem. anal.;

copper(II) choride dihydrate + DL-methionine-S-methylsulfonium chloride (3493-12-7) + glycine (56-40-6) → CuCl2(H2NCH2COO)(H2O)2(1-)*HO2CCH(NH2)CH2CH2S(CH3)2(1+)*2H2O={CuCl2(H2NCH2COO)(H2O)2}(HO2CCH(NH2)CH2CH2S(CH3)2)*2H2O

Conditions	Yield
In ethanol; water addn. of Cu-salt in EtOH to saturated aq. soln. of ligands, stirred until no further decolourisation of the supernatant liquid; sepn. of the mother-liquor, residue treated two or three times with EtOH and with acetone until the organic solvent gave negative test for Cl(1-), powdered product washed three times with ether; elem. anal.;

copper(II) choride dihydrate + DL-methionine-S-methylsulfonium chloride (3493-12-7) + aspartic Acid (617-45-8) → CuCl2(HOOCCH2CHNH2COO)(H2O)2(1-)*HO2CCHNH2CH2CH2S(CH3)2(1+)={CuCl2(HOOCCH2CHNH2COO)(H2O)2}{HO2CCHNH2CH2CH2S(CH3)2}

Conditions	Yield
In ethanol; water addn. of Cu-salt in EtOH to saturated aq. soln. of ligands, stirred until no further decolourisation of the supernatant liquid; sepn. of the mother-liquor, residue treated two or three times with EtOH and with acetone until the organic solvent gave negative test for Cl(1-), powdered product washed three times with ether; elem. anal.;

copper(II) choride dihydrate + DL-methionine-S-methylsulfonium chloride (3493-12-7) + rac-Ala-OH (302-72-7) → Cu(2+)*2Cl(1-)*CH3CH(NH2)COO(1-)*H2O*HO2CCH(NH2)CH2CH2S(CH3)2(1+)={CuCl2(CH3CH(NH2)COO)(H2O)}(HO2CCH(NH2)CH2CH2S(CH3)2)

Conditions	Yield
In ethanol; water addn. of Cu-salt in EtOH to saturated aq. soln. of ligands, stirred until no further decolourisation of the supernatant liquid; sepn. of the mother-liquor, residue treated two or three times with EtOH and with acetone until the organic solvent gave negative test for Cl(1-), powdered product washed three times with ether; elem. anal.;

iron(III) chloride hexahydrate + S-methyl-L-cysteine (1187-84-4) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Fe(3+)*O2CCH(NH2)CH2CH2S(CH3)2*Cl(1-)*2O2CCH(NH2)CH2SCH3(1-)*3H2O=Fe(O2CCH(NH2)CH2CH2S(CH3)2Cl)(O2CCH(NH2)CH2SCH3)2*3H2O

Conditions	Yield
In water addn. of FeCl3*6H2O to a mixt. of vitamin U and S-methyl-L-cysteine in water (molar ratio 1:1:2), addn. of LiCO3 in small portions, liberation of CO2; complex isolated from the soln. by addn. of a 1:1 mixt. of acetone and alcohol, oily ppt., treated with acetone to give a powder, washed with ether; elem. anal.;

α-ketoglutaric acid (328-50-7) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + zinc(II) oxide → Zn(O2CC(O)CH2CH2CO2H)(O2CCH(NH2)(CH2)2S(CH3)2)(H2O)(1+)*Cl(1-)=Zn(O2CC(O)CH2CH2CO2H)(O2CCH(NH2)(CH2)2S(CH3)2Cl)*H2O

Conditions	Yield
In water react. with ZnO with stirring until dissolution of the ZnO; salting-out with acetone, elem. anal.;

nickel(II) carbonate (719261-06-0) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + glycine (56-40-6) → Ni((CH3)2SCH2CH2CH(NH2)COO)(CH2(NH2)COO)(1+)(H2O)2*Cl(1-)=Ni((CH3)2S(Cl)CH2CH2CH(NH2)COO)(CH2(NH2)COO)*2H2O

Conditions	Yield
In water addn. of basic NiCO3 to equimolar quantities of the ligands dissolved in water; filtration, salting-out by repeated treating with acetone, elem. anal.;

nickel(II) carbonate (719261-06-0) + DL-methionine-S-methylsulfonium chloride (3493-12-7) + aspartic Acid (617-45-8) → Ni((CH3)2SCH2CH2CH(NH2)COO)(COOCH(NH3)CH2COO)(H2O)2(1+)*Cl(1-)*H2O=Ni((CH3)2S(Cl)C3H5(NH2)COO)(COOCH(NH3)CH2COO)*3H2O

Conditions	Yield
In water addn. of basic NiCO3 to equimolar quantities of the ligands dissolved in water; filtration, salting-out by repeated treating with acetone, elem. anal.;

ferric hydroxide + S-methyl-L-cysteine (1187-84-4) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Fe(3+)*2O2CCHNH2CH2CH2S(CH3)2*2Cl(1-)*O2CCH(NH2)CH2SCH3(1-)*2H2O=Fe(O2CCH(NH2)CH2CH2S(CH3)2Cl)2(O2CCH(NH2)CH2SCH3)*2H2O

Conditions	Yield
In water addn. of vitamin U and S-methyl-L-cysteine to metal hydroxide in water (molar ratio 2:1:1), stirred to give a soln.; addn. of acetone; elem. anal.;

ferric hydroxide + S-methyl-L-cysteine (1187-84-4) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Fe(3+)*O2CCH(NH2)CH2CH2S(CH3)2*Cl(1-)*2O2CCH(NH2)CH2SCH3(1-)=Fe(O2CCH(NH2)CH2CH2S(CH3)2Cl)(O2CCH(NH2)CH2SCH3)2

Conditions	Yield
In water addn. of Fe(OH)3 to a mixt. of vitamin U and S-methyl-L-cysteine in water (molar ratio 1:1:2); complex isolated from the soln. by addn. of a 1:1 mixt. of acetone and alcohol, oily ppt., treated with acetone to give a powder, washed with ether; elem. anal.;

ferric hydroxide + rac-cysteine (921-01-7, 3374-22-9, 4371-52-2, 40143-64-4, 40143-66-6, 40143-69-9, 52-90-4) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Fe(3+)*(O2CCH(NH2)CH2CH2S(CH3)2Cl)(1-)*2(O2CCH(NH2)CH2SH)(1-)*4H2O=Fe(O2CCH(NH2)CH2CH2S(CH3)2Cl)(O2CCH(NH2)CH2SH)2*4H2O

Conditions	Yield
In water addn. of vitamin U and cysteine to metal hydroxide in water (molar ratio 1:2:1), stirred (6 d), loose ppt.; sepn. of the ppt. from the supernatant liquid, treated with acetone, when it became viscous, treated with acetone to give a powder, washed with ether; elem. anal.;

ferric hydroxide + rac-cysteine (921-01-7, 3374-22-9, 4371-52-2, 40143-64-4, 40143-66-6, 40143-69-9, 52-90-4) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Fe(O2CCH(NH2)CH2CH2S(CH3)2)2(O2CCH(NH3)CH2S)(2+)*2Cl(1-)*3H2O=Fe(O2CCH(NH2)CH2CH2S(CH3)2Cl)2(O2CCH(NH3)CH2S)*3H2O

Conditions	Yield
In water addn. of vitamin U and cysteine to metal hydroxide in water (molar ratio 2:1:1), stirred (6 d), loose ppt.; sepn. of the ppt. from the supernatant liquid, treated with acetone, when it became viscous, treated with acetone to give a powder, washed with ether; elem. anal.;

chromium(III) hydroxide + rac-cysteine (921-01-7, 3374-22-9, 4371-52-2, 40143-64-4, 40143-66-6, 40143-69-9, 52-90-4) + DL-methionine-S-methylsulfonium chloride (3493-12-7) → Cr(O2CCH(NH2)CH2CH2S(CH3)2)(O2CCH(NH2)CH2S)(H2O)(1+)*Cl(1-)*H2O=Cr(O2CCH(NH2)CH2CH2S(CH3)2Cl)(O2CCH(NH2)CH2S)(H2O)*H2O

Conditions	Yield
In water addn. of vitamin U and cysteine to metal hydroxide in water (molar ratio 1:1:1), stirred (4 d), pptn.; treatment with acetone; elem. anal.;

Upstream product

• 63-68-3 L-methionine 
• 74-88-4 methyl iodide 

Downstream Products

• 74-83-9 methyl bromide 
• 74-87-3 methylene chloride 
• 74-88-4 methyl iodide 
• 75-18-3 dimethylsulfide 
• 672-15-1 L-homoserine 

Relevant articles and documents

Double-headed sulfur-linked amino acids as first inhibitors for betaine-homocysteine S -methyltransferase 2

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.