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Methylmethionine sulfonium chloride

Alias: FEMA No. 3445; EINECS 214-231-1; Methylmethionine sulfonium chloride
Cat No.:V15911 Purity: ≥98%
Vitamin U (S-Methylmethionine sulfonium) chloride is an oral antiulcer agent with anti-oxidant effect.
Methylmethionine sulfonium chloride
Methylmethionine sulfonium chloride Chemical Structure CAS No.: 1115-84-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Vitamin U (S-Methylmethionine sulfonium) chloride is an oral antiulcer agent with anti-oxidant effect. Vitamin U chloride inhibits adipocyte differentiation. Vitamin U chloride promotes skin wound healing. Vitamin U chloride may be utilized in the research/study of gastrointestinal ulcers.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Human dermal fibroblasts (hDF) are encouraged to proliferate and migrate when exposed to 100 μM of vitamin U chloride for 24 hours [1]. For a 24-hour period, vitamin U chloride (0–1 mM) activates ERK1/2 in hDF[1]. Higher plants subjected to low temperature stress can benefit from the reduction of cell membrane damage caused by chlorinated vitamin U (0.1 g/L in nutritional solution) [2]. Adipocyte development is inhibited by vitamin U chloride (10–100 mM, 7 days) through the upregulation of AMPK activation and the downregulation of adipogenic factors [3].
ln Vivo
In rats, valproic acid-induced liver damage can be avoided by administering 50 mg/kg of vitamin U chloride orally [4]. Rats exposed to 50 mg/kg of vitamin U chloride orally for three days show antioxidant benefits and are less likely to develop stomach injury from GalN [5].
Cell Assay
Cell proliferation experiment [1]
Cell Types: human dermal fibroblasts (hDFs)
Tested Concentrations: 100 μM
Incubation Duration: 24 h
Experimental Results: Promote the proliferation of hDFs.

Western Blot Analysis[3]
Cell Types: 3T3-L1 Cell
Tested Concentrations: 50, 70, 90 mM
Incubation Duration: 7 days
Experimental Results: Increased AMPK phosphorylation and diminished PPAR-γ levels.
Animal Protocol
Animal/Disease Models: Valproic acid (VPA) induced liver injury in rats [4]
Doses: 50 mg/kg
Route of Administration: po (oral gavage)
Experimental Results: Blocked catalase (CAT), glutathione reductase (GR) ), glutathione peroxidase (GPx), and superoxide dismutase (SOD) activities. IL-1β, active caspase-3, and cytoplasmic cytochrome c levels were increased. The number of proliferating cell nuclear antigen (PCNA)-positive hepatocytes increased.
References

[1]. Accelerated wound healing by S-methylmethionine sulfonium: evidence of dermal fibroblast activation via the ERK1/2 pathway. Pharmacology. 2010;85(2):68-76.

[2]. S-methylmethionine reduces cell membrane damage in higher plants exposed to low-temperature stress. J Plant Physiol. 2008 Sep 29;165(14):1483-90.

[3]. Inhibitory Effect of Vitamin U (S-Methylmethionine Sulfonium Chloride) on Differentiation in 3T3-L1 Pre-adipocyte Cell Lines. Ann Dermatol. 2012 Feb;24(1):39-44.

[4]. Vitamin U prevents valproic acid-induced liver injury through supporting enzymatic antioxidant system and increasing hepatocyte proliferation triggered by inflammation and apoptosis. Toxicol Mech Methods. 2021 Oct;31(8):600-608.

[5]. Gastroprotective effect of vitamin U in D-galactosamine-induced hepatotoxicity. J Biochem Mol Toxicol. 2022 Sep;36(9):e23124.

Additional Infomation
Methylmethionine sulfonium salt is an organic molecular entity.
Methylmethionine chloride may be useful in helping the healing of gastric ulcers. In Japan, it is used as an over the counter product for gastrointestinal health support. It is also called "Vitamin U", but it is not a true vitamin.
A vitamin found in green vegetables. It is used in the treatment of peptic ulcers, colitis, and gastritis and has an effect on secretory, acid-forming, and enzymatic functions of the intestinal tract.
See also: Cabbage (annotation moved to).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C6H14CLNO2S
Molecular Weight
199.693
Exact Mass
199.043
CAS #
1115-84-0
PubChem CID
16217806
Appearance
Off-white to light yellow solid powder
Melting Point
134ºC
LogP
1.168
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
11
Complexity
116
Defined Atom Stereocenter Count
1
SMILES
C[S+](C)CC[C@@H](C(=O)O)N.[Cl-]
InChi Key
MYGVPKMVGSXPCQ-JEDNCBNOSA-N
InChi Code
InChI=1S/C6H13NO2S.ClH/c1-10(2)4-3-5(7)6(8)9;/h5H,3-4,7H2,1-2H3;1H/t5-;/m0./s1
Chemical Name
[(3S)-3-amino-3-carboxypropyl]-dimethylsulfanium;chloride
Synonyms
FEMA No. 3445; EINECS 214-231-1; Methylmethionine sulfonium chloride
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.0078 mL 25.0388 mL 50.0776 mL
5 mM 1.0016 mL 5.0078 mL 10.0155 mL
10 mM 0.5008 mL 2.5039 mL 5.0078 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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