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S-methyl methioninium chloride

Chemical Structure

General Material Information

Preferred name S-methyl methioninium chloride
Trivial Name Vitamin U
Short Description L-methylmethioninesulphonium chloride
Formula C6 H14 Cl N O2 S
CAS Number 1115-84-0
ECHA Number 214-231-1
FDA UNII G9CUR2204U
NMR Predictor External link
Synonyms
  • (S)-(3-amino-3-carboxypropyl) dimethyl sulfonium chloride
  • laevo-(3-amino-3-carboxypropyl) dimethyl sulfonium chloride
  • laevo-(S)-(3-amino-3-carboxypropyl) dimethyl sulfonium chloride
  • L-(3-amino-3-carboxypropyl)dimethylsulfonium chloride
  • L-(3-amino-4-hydroxy-4-oxobutyl)-dimethylsulfanium chloride
  • laevo-(3-amino-4-hydroxy-4-oxobutyl)-dimethylsulfanium chloride
  • ardesyl
  • cabagin
  • epadyn-U
  • merastom
  • laevo- methyl methionine sulfonum chloride
  • S- methylmethionine
  • L- methylmethioninesulfonum chloride
  • L- methylmethioninesulphonium chloride
  • S- methylmethioninesulphonium chloride
  • S- methylmethioninium chloride
  • S- methymethionine chloride
  • u-vit
  • vitamin U
  • yucron
  • [(3S)-3-amino-3-carboxypropyl](dimethyl)sulfonium chloride
  • [(3S)-3-amino-3-carboxypropyl](dimethyl)sulfonium chloride
  • Sulfonium, [(3S)-3-amino-3-carboxypropyl]dimethyl-, chloride (1:1)
  • Sulfonium, (3-amino-3-carboxypropyl)dimethyl-, chloride, L-
  • Sulfonium, (3-amino-3-carboxypropyl)dimethyl-, chloride, (S)-
  • Sulfonium, [(3S)-3-amino-3-carboxypropyl]dimethyl-, chloride
  • Methylmethioninesulfonium chloride
  • L-Methylmethionine sulfonium chloride
  • S-Methylmethionine sulfonium chloride
  • L-Methionine methylsulfonium chloride
  • S-Methylmethionine chloride
  • Epadyn U
  • Cabagin U
  • Methionine-S-methyl sulfonium chloride
  • MMSC
  • Vitas U

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Literature & References

[(3S)-3-amino-3-carboxypropyl](dimethyl)sulfonium chloride
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1115-84-0
Pubchem (cid):16217806
Pubchem (sid):134979450
Publications by PubMed
Vitamin U has a protective effect on valproic acid-induced renal damage due to its anti-oxidant, anti-inflammatory, and anti-fibrotic properties.
Vitamin U, a novel free radical scavenger, prevents lens injury in rats administered with valproic acid.
Dimethyl sulfide as a source of the seaweed-like aroma in cooked soybeans and correlation with its precursor, S-methylmethionine (vitamin U).
Comparison of amino acid positron emission tomographic radiotracers for molecular imaging of primary and metastatic brain tumors.
Comparative metabolite profiling of foxglove aphids (Aulacorthum solani Kaltenbach) on leaves of resistant and susceptible soybean strains.
Digestive recovery of sulfur-methyl-L-methionine and its bioaccessibility in Kimchi cabbages using a simulated in vitro digestion model system.
A novel automethylation reaction in the Aspergillus nidulans LaeA protein generates S-methylmethionine.
Comparison of GC-MS and NMR for metabolite profiling of rice subjected to submergence stress.
Effects of vitamin U (S-methyl methionine sulphonium chloride) on valproic acid induced liver injury in rats.
Agrobacterium tumefaciens can obtain sulphur from an opine that is synthesized by octopine synthase using S-methylmethionine as a substrate.
Inhibitory Effect of Vitamin U (S-Methylmethionine Sulfonium Chloride) on Differentiation in 3T3-L1 Pre-adipocyte Cell Lines.
Vitamin U-bonded stationary phase in capillary ion chromatography.
S-methylmethionine is involved in the salinity tolerance of Arabidopsis thaliana plants at germination and early growth stages.
Effects of Zn(II) complex with vitamins C and U, and carnitine on metabolic syndrome model rats.
Increased phloem transport of S-methylmethionine positively affects sulfur and nitrogen metabolism and seed development in pea plants.
Changes in saccharide, amino acid and S-methylmethionine content during malting of barley grown with different nitrogen and sulfur status.
Accelerated wound healing by S-methylmethionine sulfonium: evidence of dermal fibroblast activation via the ERK1/2 pathway.
An integrative genomic analysis identifies Bhmt2 as a diet-dependent genetic factor protecting against acetaminophen-induced liver toxicity.
Quantitation of S-methylmethionine in raw vegetables and green malt by a stable isotope dilution assay using LC-MS/MS: comparison with dimethyl sulfide formation after heat treatment.
Effects of combination treatment with famotidine and methylmethionine sulfonium chloride on the mucus barrier of rat gastric mucosa.
Identification of S-methylmethionine in Petit Manseng grapes as dimethyl sulphide precursor in wine.
S-methylmethionine reduces cell membrane damage in higher plants exposed to low-temperature stress.
Betaine-homocysteine S-methyltransferase-2 is an S-methylmethionine-homocysteine methyltransferase.
Effect of s-methylmethionine sulphonium chloride on oesophagogastric ulcers in pigs.
[Positron emission tomography with L-[S-methyl-11C]-methioine and its biodistribution].
[Studying the anti-ulcer activity of gastrobiol].
Comparative species utilization and toxicity of sulfur amino acids.
The expression level of threonine synthase and cystathionine-gamma-synthase is influenced by the level of both threonine and methionine in Arabidopsis plants.
Dietary S-methylmethionine, a component of foods, has choline-sparing activity in chickens.
Ability of possible DMS precursors to release DMS during wine aging and in the conditions of heat-alkaline treatment.
Unusual accumulation of S-methylmethionine in aerobic-etiolated and in anoxic rice seedlings: an 1H-NMR study.
S-methylmethionine is both a substrate and an inactivator of 1-aminocyclopropane-1-carboxylate synthase.
Insertional inactivation of the methionine s-methyltransferase gene eliminates the s-methylmethionine cycle and increases the methylation ratio.
The activation of c-Jun NH2-terminal kinase (JNK) by DNA-damaging agents serves to promote drug resistance via activating transcription factor 2 (ATF2)-dependent enhanced DNA repair.
S-adenosylmethionine conformations in solution and in protein complexes: conformational influences of the sulfonium group.
The N-terminal region of Arabidopsis cystathionine gamma-synthase plays an important regulatory role in methionine metabolism.
Constitutive overexpression of cystathionine gamma-synthase in Arabidopsis leads to accumulation of soluble methionine and S-methylmethionine.
[The effect of cobavit on glutathione system in patients with bleeding gastroduodenal ulcer].
The S-methylmethionine cycle in angiosperms: ubiquity, antiquity and activity.
Mechanisms to account for maintenance of the soluble methionine pool in transgenic Arabidopsis plants expressing antisense cystathionine gamma-synthase cDNA.
Reverse methionine biosynthesis from S-adenosylmethionine in eukaryotic cells.
Differential labelling of sphingolipids by [3H]serine and ([3H]methyl)-methionine in fish leukocytes.
Augmentative effects of L-cysteine and methylmethionine sulfonium chloride on mucin secretion in rabbit gastric mucous cells.
S-methylmethionine plays a major role in phloem sulfur transport and is synthesized by a novel type of methyltransferase.
A family of S-methylmethionine-dependent thiol/selenol methyltransferases. Role in selenium tolerance and evolutionary relation.
S-methylmethionine metabolism in Escherichia coli.
[The anti-ulcer action of dibunol (Tonarol)].
Dimethylsulfoniopropionate biosynthesis in Spartina alterniflora1. Evidence that S-methylmethionine and dimethylsulfoniopropylamine are intermediates.
Salinity promotes accumulation of 3-dimethylsulfoniopropionate and its precursor S-methylmethionine in chloroplasts.
Late-infantile ceroid-lipofuscinosis: lysine methylation of mitochondrial ATP synthase subunit c from lysosomal storage bodies.
[Radiation-protective effect of S-methylmethionine (vitamin U)].
S-methylmethionine sulfonium in fruits of citrus hybrids.
Methionine derivatives diminish sulphide damage to colonocytes--implications for ulcerative colitis.
Mechanisms for cytoprotection by vitamin U from ethanol-induced gastric mucosal damage in rats.
Purification and properties of S-adenosyl-L-methionine:L-methionine S-methyltransferase from Wollastonia biflora leaves.
Effect of hammer mill screen size and addition of fibre or S-methylmethionine-sulphonium chloride to the diet on the occurrence of oesophagogastric lesions in fattening pigs.
[Determination of taurine, L-glutamine, vitamin U and L-aspartic acid in pharmaceuticals by high-performance liquid chromatography with pre-column derivatization].
Biosynthesis of 3-dimethylsulfoniopropionate in Wollastonia biflora (L.) DC. Evidence that S-methylmethionine is an intermediate.
Sulfhydryl-containing agents in the treatment of gastric bleeding induced by nonsteroidal anti-inflammatory drugs.
Protection against chronic gastric ulceration in the rat with sulfhydryl-containing agents.
[The nutritional prevention of postradiation effects].
Role of sulfhydryl-containing agents in the healing of erosive gastritis and chronic gastric ulceration in the rat.
Sulphydryl-containing agents: a new approach to the problem of refractory peptic ulceration.
Sulphydryl-containing agents stimulate the healing of duodenal ulceration in man.
Role of sulphydryl-containing agents in the management of recurrent attacks of ulcerative colitis. A new approach.
Administration of sulfhydryls to stimulate the healing of ischemia-induced acute gastric mucosal injury in the rat.
Clinical value of PET with 18F-fluorodeoxyglucose and L-methyl-11C-methionine for diagnosis of recurrent brain tumor and radiation injury.
[Metabolism of S-methylmethionine (vitamin U) in animals].
[The effect of methylation on the carnitine synthesis].
[Increase of the functional activity of natural killers under the effects of the pharmacological correction of the sympathoadrenal system state in patients with lung cancer].
Role of oxygen-derived free radicals in mechanism of acute and chronic duodenal ulceration in the rat.
Determination of vitamin U and its degradation products by high- performance liquid chromatography with fluorescence detection.
[Effect of vitamin U on the colony formation of oral epithelial cells in vitro].
[Effect of various factors on the methylation of DNAse I].
[Effect of quaterin and S-methylmethionine on the intensity of chromatin protein methylation].
[S-methyl methionine (vitamin U) pharmacokinetics in rat and man].
[Effect of sea buckthorn oil on various pathophysiologic mechanisms and the course of peptic ulcer].
Analysis of S-methylmethionine and S-adenosylmethionine in plant tissue by a dansylation, dual-isotope method.
[Use of vitamin U electrophoresis with duodenal peptic ulcer patients].
[Anti-ulcer action of the sodium salt of N-(4-sulfolanol-3-yl) methionine].
[Ulcer-fiber-cabbage and vitamin U].
Modulation of phospholipid methylation in rabbit leukocytes by indomethacin.
Oesophagogastric ulcer in swine and vitamin U. IV. Efficiency of the Hungarian vitamin U preparation in reduction of economic losses.
Oesophagogastric ulcer in swine and vitamin U. III. Reduction of economic losses by vitamin U.
[Correction of the function of the sympathoadrenal system in the surgical and combined treatment of patients with cancer of the esophagus and stomach].
Therapeutic and preventive effects of saponin of ginseng fruit on experimental gastric ulcers.
Relationships between phosphoenolpyruvate synthesis and glutamine formation in isolated chicken liver mitochondria.
Nerve growth factor stimulates phospholipid methylation in target ganglionic neurons independently of the cyclic AMP and sodium pump responses.
The effect of cholesterol on ubiquinone and tetrahymanol biosynthesis in Tetrahymena pyriformis.
Myofibrillar protein turnover. Synthesis of protein-bound 3-methylhistidine, actin, myosin heavy chain and aldolase in rat skeletal muscle in the fed and starved states.
Gas-liquid and column liquid chromatography for studying vitamin U metabolism in humans and animals.
Mutagenic action of S-methylmethionine in bacteria.
Oesophagogastric ulcer in swine and vitamin U. II. Nature of vitamin U.
Oesophagogastric ulcer in swine and vitamin U. I. Relative incidence of the syndrome in Hungary.
Preparation of 11C-methyl iodide and L-[S-methyl-11C]methionine by an automated continuous flow process.
A new radioactive drug selectively accumulating in Melanoma cells.
[DNA methylation in the cells of Escherichia coli MRE 600 in the presence of S-methylmethionine].
[Vitamin U and RNA metabolism in prokaryotes].
[Natural sources of vitamin U and its retention in nutritional products].
Preparation and 13C NMR characterization of [[epsilon-13C] methionine-192]-alpha-chymotrypsin. The demethylation of [S-[13C] methylmethionine-192]-alpha-chymotrypsin by an active site-directed thiol.
[Influence of S-methylmethionine on the metabolism of nucleic acids in Escherichia coli].
[Treatment of depressive conditions with S-methylmethionine (vitamin U)].
Hypolipidemic effect of L-form S-methylmethionine sulfonium chloride in man.
[Gastrointestinal bleeding complicating burn injuries and its prevention (author's transl)].
[tRNA methyltransferase activity in Escherichia coli growing on a medium with methionine and S-methylmethionine].
Toxicology of glucosinolates, related compounds (nitriles, R-goitrin, isothiocyanates) and vitamin U found in Cruciferae.
A possible activation of cholesterol 7-hydroxylation by S-methylmethionine (vitamin U).
Comparative effects of S-methylmethionine (vitamin U) and methionine on choline-deficient fatty liver in rats.
Hypolipidemic effects of S-methylmethionine (vitamin U) using various experimental procedures.
Protein methylation: cytochrome c methylation as a model system.
Effects of S-methylmethionine (vitamin U) on experimental nephrotic hyperlipidemia.
Mode of hypocholesterolemic action of S-methylmethionine (vitamin U) in mice.
Normalizing effects of S-methylmethionine (vitamin U) on lipoprotein disorder in rats.
[The mechanism of action of S-methylmethionine].
[Therapeutic use of vitamin U in gastroenterological practice].
[Kraurosis vulvae (problems of pathogenesis and therapy)].
Hypolipidemic effects of S-methylmethionine (vitamin U) using various experimental procedures.
[Gas chromatographic determination of S-methylmethionine (vitamin U) in plants].
[Use of methylmethioninesulfonium chloride in active forms of rheumatism].
[Anti-inflammatory effect of methylmethionine sulfonium chloride (vitamin U)].
[Clinical effect and an analysis of the mechanism of action of vitamin U (S-methylmethioninesulfonium chloride) in peptic ulcer of the stomach and duodenum].
[Method of electrophoretic determination of S-methyl methionine in plants].
[Therapeutic effectiveness of methylmethioninesulfonium chloride (vitamin U) in patients with chronic enterocolitis].
[Therapeutic effect of MMSC1 (vitamin U) on gastric and intestinal function in the treatment of patients with chronic gastritis].
[Effect of complex treatment including casein hydrolysate and vitamin U on the protein-amino acid spectrum of the blood in patients with peptic ulcer].
[Data on the therapeutic use of vitamin U].
[Methylmethioninesulfonium chloride (vitamin U)].
[Methylmethionine (vitamin U) metabolism in mammals].
[The effect of S-methylmethionine (vitamin U) on the acid-forming function of the stomach in peptic ulcer].
[From ancient brassicotherapy to vitamin U].
[Clinical results of the experimentation of vitamin U].
[The therapeutic value of so-called vitamin "U" in the treatment of ulcers--a clinical judgment].
[A new therapy of peptic ulcer: "the anti-ulcer factor of cabbage" ("vitamin U")].
[ON THE SYNTHESIS OF METHIONINE METHYL SULFONIUM SALTS (VITAMIN U)].
[On a case of ulcer treated with a new preparation with a base of "vitamin U" and urogastrone].
[Vitamin U-1 (anti-ulcer factor)].
[Study of the mechnism of action of so-called "vitamin U" with histochemical reactions].
[Is the pharmacological property of vitamin U specific? II. The effect of quercetin on experimental gastric ulcer induced by histamine and antihistaminics].
[Vitamin U, a hypothetic anti-ulcer factor].
[Contribution to the knowledge of the ulcer-preventive factor (so-called vitamin U) intestinal activity of vitamin U-containing dry extracts of cabbage. II].
[A contribution to ulcer prevention factors, so-called vitamin U. I].
[Histological effect of vitamin U on ulcers induced on the stomach of dogs].
[Vitamin U (anti-ulcer factor), contained in cabbage juice, etc., as a possible means of correcting late dumping syndrome].
[Treatment of peptic ulcer disease of stomach & duodenum with vitamin U].
Vitamin U therapy of peptic ulcer; experience at San Quentin Prison.
The medical management of gastric ulcers with vitamin U therapy.
[The present state of so-called vitamin U therapy of peptic ulcer].
Vitamin U concentrate therapy of peptic ulcer.
[Treatment of peptic ulcer with cabbage juice and banana frappé (anti-ulcus factor, Vitamin U)].
Vitamin U therapy of peptic ulcer.
Anti-peptic ulcer dietary factor (vitamin "U") in the treatment of peptic ulcer.
Rapid healing of peptic ulcers in patients receiving fresh cabbage juice.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
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KEGG (GenomeNet):C04078
HMDB (The Human Metabolome Database):Search
FooDB:FDB018071
Export Tariff Code:2936.90.0000
FDA Listing of Food Additive Status:View
VCF-Online:VCF Volatile Compounds in Food
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Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 199.69998168945
Melting Point 134 to 139°C @ 760 mm Hg
Flash Point TCC Value N/a
logP (o/w) 0.28
Solubility
alcohol Yes
water Yes
water, 215.8 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Malty
malty, tomato, potato, sulfurous, green
General comment At 100.00 %. malty tomato potato sulfury green
Mosciano, Gerard P&F 17, No. 6, 41, (1992) Malty, tomato, methional, sulfureous, with a green nuance
Flavor Type: Sulfurous
sulfurous, creamy, tomato, malty, vegetable
Mosciano, Gerard P&F 17, No. 6, 41, (1992) At 5.00 ppm. Sulfureous creamy, tomato, malty, vegetable like

Occurrences

Potential Uses

Applications
Flavoring purposes Corn , Potato , Tomato , Vegetable

Safety Information

Safety information

Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 > 6000 mg/kg
Drugs in Japan Vol. 6, Pg. 835, 1982.

intravenous-mouse LD50 259 mg/kg
Drugs in Japan Vol. 6, Pg. 835, 1982.

intravenous-rat LD50 432 mg/kg
Drugs in Japan Vol. 6, Pg. 835, 1982.

oral-rat LD50 > 6000 mg/kg
Drugs in Japan Vol. 6, Pg. 835, 1982.

Dermal Toxicity:
subcutaneous-mouse LD50 > 6000 mg/kg
Drugs in Japan Vol. 6, Pg. 835, 1982.

subcutaneous-rat LD50 > 6000 mg/kg
Drugs in Japan Vol. 6, Pg. 835, 1982.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
antioxidants and preservatives for fragrance and flavor
Recommendation for S-methyl methioninium chloride usage levels up to:
not for fragrance use.
Recommendation for S-methyl methioninium chloride flavor usage levels up to:
not for flavor use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 350.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 75.00 (μg/capita/day)
Structure Class: III

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 79, (FGE.79)[1] - Consideration of amino acids and related substances evaluated by JECFA (63rd meeting) structurally related to amino acids from chemical group 34 evaluated by EFSA in FGE.26Rev1 (2008)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 96 (FGE.96): Consideration of 88 flavouring substances considered by EFSA for which EU production volumes / anticipated production volumes have been submitted on request by DG SANCO. Addendum to FGE. 51, 52, 53, 54, 56, 58, 61, 62, 63, 64, 68, 69, 70, 71, 73, 76, 77, 79, 80, 83, 84, 85 and 87.
View page or View pdf

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EPA Substance Registry Services (TSCA):1115-84-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :16217806
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
[(3S)-3-amino-3-carboxypropyl](dimethyl)sulfonium chloride
Chemidplus:0001115840