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MedKoo Cat#: 341269 | Name: Methylmethionine sulfonium chloride

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methylmethionine sulfonium chloride is a biochemical.

Chemical Structure

Methylmethionine sulfonium chloride
Methylmethionine sulfonium chloride
CAS#1115-84-0

Theoretical Analysis

MedKoo Cat#: 341269

Name: Methylmethionine sulfonium chloride

CAS#: 1115-84-0

Chemical Formula: C6H14ClNO2S

Exact Mass: 199.0434

Molecular Weight: 199.69

Elemental Analysis: C, 36.09; H, 7.07; Cl, 17.75; N, 7.01; O, 16.02; S, 16.05

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Synonym
Methylmethionine sulfonium chloride; EINECS 214-231-1; FEMA No. 3445.
IUPAC/Chemical Name
(S)-(3-Amino-3-carboxypropyl)dimethylsulfonium chloride
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
SMILES Code
C[S+](CC[C@H](N)C(O)=O)C.[Cl-]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methylmethionine sulfonium chloride is a biochemical.
In vitro activity:
S-methylmethionine sulfonium chloride was originally called vitamin U because of its inhibition of ulceration in the digestive system. This study was designed to evaluate the anti-obesity effect of vitamin U in 3T3-L1 pre-adipocyte cell lines. There was a gradual decrease in the level of TGs, C/EBP-α, PPAR-γ, adipsin, ADD-1 and GPDH activity with increasing concentrations of vitamin U. In contrast, we observed a significant increase in AMPK activity with increasing levels of vitamin U. Reference: Ann Dermatol. 2012 Feb;24(1):39-44. https://pubmed.ncbi.nlm.nih.gov/22363154/
In vivo activity:
The present study was designed to investigate the protective effects of Vit U (methylmethionine sulfonium chloride) on GalN (galactosamine)-induced stomach injury. Rats were divided into four groups as follows: control (group I), Vit U given animals (50 mg/kg per day; group II), GalN administered animals (500 mg/kg at a single dose; group III), GalN + Vit U given animals (at the same dose and time, group IV). In comparison to the control group, glutathione, total antioxidant capacity levels, catalase, superoxide dismutase, glutathione peroxidase, glutathione reductase, glutathione-S-transferase, and Na+ /K+ -ATPase activities of GalN group were found to be decreased. On the contrary, lipid peroxidation, advanced oxidized protein products, hexose-hexosamine, fucose, sialic acid, reactive oxygen species levels, as well as the activities of myeloperoxidase, xanthine oxidase, and lactate dehydrogenase were elevated. Administration of Vit U reversed these abnormalities in the GalN group. Reference: J Biochem Mol Toxicol. 2022 Sep;36(9):e23124. https://pubmed.ncbi.nlm.nih.gov/35670011/

Preparing Stock Solutions

The following data is based on the product molecular weight 199.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lee NY, Park KY, Min HJ, Song KY, Lim YY, Park J, Kim BJ, Kim MN. 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. doi: 10.5021/ad.2012.24.1.39. Epub 2012 Feb 2. PMID: 22363154; PMCID: PMC3283849. 3. Rácz I, Páldi E, Szalai G, Janda T, Pál M, Lásztity D. S-methylmethionine reduces cell membrane damage in higher plants exposed to low-temperature stress. J Plant Physiol. 2008 Sep 29;165(14):1483-90. doi: 10.1016/j.jplph.2006.03.020. Epub 2008 Feb 19. PMID: 18242766. 1. Topaloglu D, Turkyilmaz IB, Yanardag R. Gastroprotective effect of vitamin U in D-galactosamine-induced hepatotoxi 4. Celik E, Tunali S, Gezginci-Oktayoglu S, Bolkent S, Can A, Yanardag R. 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. doi: 10.1080/15376516.2021.1943089. Epub 2021 Aug 22. PMID: 34420476.city. J Biochem Mol Toxicol. 2022 Sep;36(9):e23124. doi: 10.1002/jbt.23124. Epub 2022 Jun 6. PMID: 35670011.
In vitro protocol:
1. Lee NY, Park KY, Min HJ, Song KY, Lim YY, Park J, Kim BJ, Kim MN. 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. doi: 10.5021/ad.2012.24.1.39. Epub 2012 Feb 2. PMID: 22363154; PMCID: PMC3283849. 2. Rácz I, Páldi E, Szalai G, Janda T, Pál M, Lásztity D. S-methylmethionine reduces cell membrane damage in higher plants exposed to low-temperature stress. J Plant Physiol. 2008 Sep 29;165(14):1483-90. doi: 10.1016/j.jplph.2006.03.020. Epub 2008 Feb 19. PMID: 18242766.
In vivo protocol:
1. Topaloglu D, Turkyilmaz IB, Yanardag R. Gastroprotective effect of vitamin U in D-galactosamine-induced hepatotoxi 2. Celik E, Tunali S, Gezginci-Oktayoglu S, Bolkent S, Can A, Yanardag R. 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. doi: 10.1080/15376516.2021.1943089. Epub 2021 Aug 22. PMID: 34420476.city. J Biochem Mol Toxicol. 2022 Sep;36(9):e23124. doi: 10.1002/jbt.23124. Epub 2022 Jun 6. PMID: 35670011.
1: Oktay S, Bayrak G, Alev B, Ipekci H, Ustundag UV, Turkyilmaz IB, Pisiriciler R, Emekli-Alturfan E, Tunali-Akbay T, Yanardag R, Yarat A. The effect of vitamin U on the lung tissue of pentyleneterazole-induced seizures in rats. Naunyn Schmiedebergs Arch Pharmacol. 2018 Feb;391(2):177-184. doi: 10.1007/s00210-017-1447-3. Epub 2017 Dec 7. PubMed PMID: 29218374. 2: Cohen H, Hacham Y, Panizel I, Rogachev I, Aharoni A, Amir R. Repression of CYSTATHIONINE γ-SYNTHASE in Seeds Recruits the S-Methylmethionine Cycle. Plant Physiol. 2017 Jul;174(3):1322-1333. doi: 10.1104/pp.17.00579. Epub 2017 May 23. PubMed PMID: 28536103; PubMed Central PMCID: PMC5490928. 3: Cohen H, Salmon A, Tietel Z, Hacham Y, Amir R. The relative contribution of genes operating in the S-methylmethionine cycle to methionine metabolism in Arabidopsis seeds. Plant Cell Rep. 2017 May;36(5):731-743. doi: 10.1007/s00299-017-2124-1. Epub 2017 Mar 13. PubMed PMID: 28289884. 4: Kim KT, Kim JS, Kim MH, Park JH, Lee JY, Lee W, Min KK, Song MG, Choi CY, Kim WS, Oh HK, Kim DD. Effect of Enhancers on in vitro and in vivo Skin Permeation and Deposition of S-Methyl-(L)-Methionine. Biomol Ther (Seoul). 2017 Jul 1;25(4):434-440. doi: 10.4062/biomolther.2016.254. PubMed PMID: 28274096; PubMed Central PMCID: PMC5499623. 5: Song JH, Lee HR, Shim SM. Determination of S-methyl-L-methionine (SMM) from Brassicaceae Family Vegetables and Characterization of the Intestinal Transport of SMM by Caco-2 Cells. J Food Sci. 2017 Jan;82(1):36-43. doi: 10.1111/1750-3841.13556. Epub 2016 Nov 24. PubMed PMID: 27883364. 6: Khrystych TN, Gontsaryuk DA. [ABOUT CO-OCCURRENCE OF CRHONIC PANCREATITIS WITH GASTRODUODENAL DISEASES]. Lik Sprava. 2015 Apr-Jun;(3-4):87-94. Review. Russian. PubMed PMID: 26827446. 7: Son YR, Choi EH, Kim GT, Park TS, Shim SM. Bioefficacy of Graviola leaf extracts in scavenging free radicals and upregulating antioxidant genes. Food Funct. 2016 Feb;7(2):861-71. doi: 10.1039/c5fo01258a. PubMed PMID: 26674326. 8: Kim WS, Seo HM, Kim WK, Choi JS, Kim I, Sung JH. The Photoprotective Effect of S-Methylmethionine Sulfonium in Skin. Int J Mol Sci. 2015 Jul 28;16(8):17088-100. doi: 10.3390/ijms160817088. PubMed PMID: 26225962; PubMed Central PMCID: PMC4581185. 9: Gezginci-Oktayoglu S, Turkyilmaz IB, Ercin M, Yanardag R, Bolkent S. Vitamin U has a protective effect on valproic acid-induced renal damage due to its anti-oxidant, anti-inflammatory, and anti-fibrotic properties. Protoplasma. 2016 Jan;253(1):127-35. doi: 10.1007/s00709-015-0796-3. Epub 2015 Mar 24. PubMed PMID: 25802006. 10: Tunali S, Kahraman S, Yanardag R. Vitamin U, a novel free radical scavenger, prevents lens injury in rats administered with valproic acid. Hum Exp Toxicol. 2015 Sep;34(9):904-10. doi: 10.1177/0960327114561665. Epub 2014 Dec 9. PubMed PMID: 25504687. 11: Frank A, Cohen H, Hoffman D, Amir R. Methionine and S-methylmethionine exhibit temporal and spatial accumulation patterns during the Arabidopsis life cycle. Amino Acids. 2015 Mar;47(3):497-510. doi: 10.1007/s00726-014-1881-1. Epub 2014 Dec 10. PubMed PMID: 25488426. 12: Morisaki A, Yamada N, Yamanaka S, Matsui K. Dimethyl sulfide as a source of the seaweed-like aroma in cooked soybeans and correlation with its precursor, S-methylmethionine (vitamin U). J Agric Food Chem. 2014 Aug 20;62(33):8289-94. doi: 10.1021/jf501614j. Epub 2014 Aug 12. PubMed PMID: 25090616. 13: Juhász C, Dwivedi S, Kamson DO, Michelhaugh SK, Mittal S. Comparison of amino acid positron emission tomographic radiotracers for molecular imaging of primary and metastatic brain tumors. Mol Imaging. 2014;13. doi: 10.2310/7290.2014.00015. Review. PubMed PMID: 24825818; PubMed Central PMCID: PMC4199087. 14: Sato D, Sugimoto M, Akashi H, Tomita M, Soga T. Comparative metabolite profiling of foxglove aphids (Aulacorthum solani Kaltenbach) on leaves of resistant and susceptible soybean strains. Mol Biosyst. 2014 Apr;10(4):909-15. doi: 10.1039/c3mb70595a. Epub 2014 Feb 11. PubMed PMID: 24514152. 15: Lee HR, Cho SD, Lee WK, Kim GH, Shim SM. Digestive recovery of sulfur-methyl-L-methionine and its bioaccessibility in Kimchi cabbages using a simulated in vitro digestion model system. J Sci Food Agric. 2014 Jan 15;94(1):109-12. doi: 10.1002/jsfa.6205. Epub 2013 May 29. PubMed PMID: 23633413. 16: Patananan AN, Palmer JM, Garvey GS, Keller NP, Clarke SG. A novel automethylation reaction in the Aspergillus nidulans LaeA protein generates S-methylmethionine. J Biol Chem. 2013 May 17;288(20):14032-45. doi: 10.1074/jbc.M113.465765. Epub 2013 Mar 26. PubMed PMID: 23532849; PubMed Central PMCID: PMC3656261. 17: Barding GA Jr, Béni S, Fukao T, Bailey-Serres J, Larive CK. Comparison of GC-MS and NMR for metabolite profiling of rice subjected to submergence stress. J Proteome Res. 2013 Feb 1;12(2):898-909. doi: 10.1021/pr300953k. Epub 2012 Dec 27. PubMed PMID: 23205590. 18: Sokmen BB, Tunali S, Yanardag R. Effects of vitamin U (S-methyl methionine sulphonium chloride) on valproic acid induced liver injury in rats. Food Chem Toxicol. 2012 Oct;50(10):3562-6. doi: 10.1016/j.fct.2012.07.056. Epub 2012 Aug 4. PubMed PMID: 22889891. 19: Flores-Mireles AL, Eberhard A, Winans SC. Agrobacterium tumefaciens can obtain sulphur from an opine that is synthesized by octopine synthase using S-methylmethionine as a substrate. Mol Microbiol. 2012 Jun;84(5):845-56. doi: 10.1111/j.1365-2958.2012.08061.x. Epub 2012 May 2. PubMed PMID: 22486934; PubMed Central PMCID: PMC3359404. 20: Lee NY, Park KY, Min HJ, Song KY, Lim YY, Park J, Kim BJ, Kim MN. 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. doi: 10.5021/ad.2012.24.1.39. Epub 2012 Feb 2. PubMed PMID: 22363154; PubMed Central PMCID: PMC3283849.