S-Methylcysteine | CAS#1187-84-4 | antioxidant | decreases oxidative stress

MedKoo Cat#: 540292 | Name: S-Methylcysteine

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Description:

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

S-Methylcysteine is an antioxidant found in Brassicaceae family plants. It decreases oxidative stress and inhibits oil drop formation in white pre-adipose tissue.

Chemical Structure

S-Methylcysteine

CAS#1187-84-4

Theoretical Analysis

MedKoo Cat#: 540292

Name: S-Methylcysteine

CAS#: 1187-84-4

Chemical Formula: C4H9NO2S

Exact Mass: 135.0354

Molecular Weight: 135.18

Elemental Analysis: C, 35.54; H, 6.71; N, 10.36; O, 23.67; S, 23.72

Price and Availability

Size	Price	Availability
5g	USD 315.00	2 weeks
25g	USD 700.00	2 weeks
100g	USD 1,650.00	2 weeks

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Related CAS #

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Synonym

S-Methyl-L-cysteine; NSC 15387; NSC15387; NSC-15387

IUPAC/Chemical Name

S-methyl-L-cysteine

InChi Key

IDIDJDIHTAOVLG-VKHMYHEASA-N

InChi Code

InChI=1S/C4H9NO2S/c1-8-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

SMILES Code

N[C@@H](CSC)C(O)=O

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 water

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:

S-methylcysteine is a natural product that acts as a substrate in the catalytic antioxidant system mediated by methionine sulfoxide reductase A (MSRA), with antioxidative, neuroprotective, and anti-obesity activities.

In vitro activity:

High S-methylcysteine concentrations reduced synaptic responses in rat hippocampal slices, that were partially reversible over time. In organotypic cultures, S-methylcysteine compromised membrane integrity at higher concentrations, while lower concentrations increased population spike amplitudes and neuronal activity without membrane damage. In dissociated neurons, S-methylcysteine acted as a competitive antagonist at GABA(A) receptors, reducing GABA-induced currents. Reference: Neurotoxicology. 2004 Sep;25(5):817-23. https://pubmed.ncbi.nlm.nih.gov/15288512/

In vivo activity:

Oral treatment of S-methylcysteine is effective in improving insulin resistance while attenuating metabolic syndrome, inflammation, and oxidative stress in male rats fed with fructose rich diet. Oral administration of S-methylcysteine for 60 days resulted in significant attenuation of plasma glucose, insulin, tumor necrosis factor-alpha, insulin resistance and improved antioxidant enzyme activities. Reference: Iran J Med Sci. 2015 Jan;40(1):45-50. https://pubmed.ncbi.nlm.nih.gov/25650289/

	Solvent	mg/mL	mM
Solubility
	Water	30.0	221.93

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 135.18 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.

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. Pancetti F, Oyarce M, Aranda M, Parodi J, Aguayo LG, Morales B, Westphal G, Müller M, Hallier E, Zeise ML. S-methylcysteine may be a causal factor in monohalomethane neurotoxicity. Neurotoxicology. 2004 Sep;25(5):817-23. doi: 10.1016/j.neuro.2004.01.008. PMID: 15288512. 2. Elmahallawy EK, Fehaid A, El-Shewehy DMM, Ramez AM, Alkhaldi AAM, Mady R, Nasr NE, Arafat N, Hassanen EAA, Alsharif KF, Abdo W. S-Methylcysteine Ameliorates the Intestinal Damage Induced by Eimeria tenella Infection via Targeting Oxidative Stress and Inflammatory Modulators. Front Vet Sci. 2022 Jan 5;8:754991. doi: 10.3389/fvets.2021.754991. PMID: 35071376; PMCID: PMC8767015. 3. Thomas S, Senthilkumar GP, Sivaraman K, Bobby Z, Paneerselvam S, Harichandrakumar KT. Effect of s-methyl-L-cysteine on oxidative stress, inflammation and insulin resistance in male wistar rats fed with high fructose diet. Iran J Med Sci. 2015 Jan;40(1):45-50. PMID: 25650289; PMCID: PMC4300480.

In vitro protocol:

In vivo protocol:

1. Elmahallawy EK, Fehaid A, El-Shewehy DMM, Ramez AM, Alkhaldi AAM, Mady R, Nasr NE, Arafat N, Hassanen EAA, Alsharif KF, Abdo W. S-Methylcysteine Ameliorates the Intestinal Damage Induced by Eimeria tenella Infection via Targeting Oxidative Stress and Inflammatory Modulators. Front Vet Sci. 2022 Jan 5;8:754991. doi: 10.3389/fvets.2021.754991. PMID: 35071376; PMCID: PMC8767015. 2. Thomas S, Senthilkumar GP, Sivaraman K, Bobby Z, Paneerselvam S, Harichandrakumar KT. Effect of s-methyl-L-cysteine on oxidative stress, inflammation and insulin resistance in male wistar rats fed with high fructose diet. Iran J Med Sci. 2015 Jan;40(1):45-50. PMID: 25650289; PMCID: PMC4300480.

1: Rubino FM, Pitton M, Di Fabio D, Meroni G, Santaniello E, Caneva E, Pappini M, Colombi A. Measurement of S-methylcysteine and S-methyl-mercapturic acid in human urine by alkyl-chloroformate extractive derivatization and isotope-dilution gas chromatography-mass spectrometry. Biomed Chromatogr. 2011 Mar;25(3):330-43. doi: 10.1002/bmc.1451. PubMed PMID: 21110385. 2: Uchino H. [Nutritional value of S-methylcysteine sulfoxide. (IV). Effect of S-methylcysteine sulfoxide supplement on rats fed a high protein-, low protein- and commercial-diet (author's transl)]. Nihon Eiseigaku Zasshi. 1975 Aug;30(3):397-403. Japanese. PubMed PMID: 1238768. 3: Refsvik T. N-acetylpenicillamine potentiated excretion of methyl mercury in rat bile: influence of S-methylcysteine. Acta Pharmacol Toxicol (Copenh). 1984 Aug;55(2):121-5. PubMed PMID: 6496113. 4: Uchino H, Itokawa Y. [Studies on nutritional value of S-methylcysteine sulfoxide. II. Splenic hypertrophy of rats on an increased S-methylcysteine sulfoxide diet and effect of S-methylcysteine sulfoxide administration on splenoectomized rats]. Nihon Eiseigaku Zasshi. 1972 Jun;27(2):253-6. Japanese. PubMed PMID: 4677395. 5: Armstrong MD. N-delta-acetylornithine and S-methylcysteine in blood plasma. Biochim Biophys Acta. 1979 Nov 1;587(4):638-42. PubMed PMID: 508804. 6: Husain A, Sato D, Jeelani G, Mi-ichi F, Ali V, Suematsu M, Soga T, Nozaki T. Metabolome analysis revealed increase in S-methylcysteine and phosphatidylisopropanolamine synthesis upon L-cysteine deprivation in the anaerobic protozoan parasite Entamoeba histolytica. J Biol Chem. 2010 Dec 10;285(50):39160-70. doi: 10.1074/jbc.M110.167304. Epub 2010 Oct 5. PubMed PMID: 20923776; PubMed Central PMCID: PMC2998131. 7: Thompson JF, Gering RK. Biosynthesis of s-methylcysteine in radish leaves. Plant Physiol. 1966 Oct;41(8):1301-7. PubMed PMID: 16656400; PubMed Central PMCID: PMC550522. 8: Zhao J, Ng CM, Chu IK, Siu KW, Hopkinson AC. Methionine, alpha-methylmethionine and S-methylcysteine radical cations: generations and dissociations in the gas phase. Phys Chem Chem Phys. 2009 Sep 21;11(35):7629-39. PubMed PMID: 19950502. 9: Uchino H. [Nutritional value of S-methylcysteine sulfoxide. 3. Comparison of S-methylcysteine sulfoxide, S-allylcysteine sulfoxide and related sulfur containing amino acids (author's transl)]. Nihon Eiseigaku Zasshi. 1973 Oct;28(4):385-91. Japanese. PubMed PMID: 4799999. 10: Yagi N, Takashima M, Itokawa Y. [Nutritional value of S-methylcysteine sulfoxide (methiin): (V). Investigations on effects of S-methylcysteine sulfoxide on methionine-substitution and amino acid imbalance (author's transl)]. Nihon Eiseigaku Zasshi. 1976 Feb;30(6):593-9. Japanese. PubMed PMID: 985941. 11: Nishikawa-Ogawa M, Wanibuchi H, Morimura K, Kinoshita A, Nishikawa T, Hayashi S, Yano Y, Fukushima S. N-acetylcysteine and S-methylcysteine inhibit MeIQx rat hepatocarcinogenesis in the post-initiation stage. Carcinogenesis. 2006 May;27(5):982-8. Epub 2005 Dec 7. PubMed PMID: 16338951. 12: Pancetti F, Oyarce M, Aranda M, Parodi J, Aguayo LG, Morales B, Westphal G, Müller M, Hallier E, Zeise ML. S-methylcysteine may be a causal factor in monohalomethane neurotoxicity. Neurotoxicology. 2004 Sep;25(5):817-23. PubMed PMID: 15288512. 13: Wei M, Wanibuchi H, Yamamoto S, Iwai S, Morimura K, Nomura T, Takayama R, Fukushima S. Chemopreventive effects of S-methylcysteine on rat hepatocarcinogenesis induced by concurrent administration of sodium nitrite and morpholine. Cancer Lett. 2000 Dec 8;161(1):97-103. PubMed PMID: 11078918. 14: Vijayaraghavan M, Wanibuchi H, Takada N, Yano Y, Otani S, Yamamoto S, Fukushima S. Inhibitory effects of S-methylcysteine and cysteine on the promoting potential of sodium phenobarbital on rat liver carcinogenesis. Jpn J Cancer Res. 2000 Aug;91(8):780-5. PubMed PMID: 10965017. 15: Buchwald AL, Müller M. Late confirmation of acute methyl bromide poisoning using S-methylcysteine adduct testing. Vet Hum Toxicol. 2001 Aug;43(4):208-11. PubMed PMID: 11474733. 16: Ro JY, Jensen DE, Kim S. Quantitation of S-methylcysteine formed in O6-methylguanine-DNA:methyltransferase. Cancer Lett. 1984 Jun;23(2):213-21. PubMed PMID: 6744245. 17: Takada N, Yano Y, Wanibuchi H, Otani S, Fukushima S. S-methylcysteine and cysteine are inhibitors of induction of glutathione S-transferase placental form-positive foci during initiation and promotion phases of rat hepatocarcinogenesis. Jpn J Cancer Res. 1997 May;88(5):435-42. PubMed PMID: 9247599. 18: Itokawa Y, Inoue K, Sasagawa S, Fujiwara M. Effect of S-methylcysteine sulfoxide, S-allylcysteine sulfoxide and related sulfur-containing amino acids on lipid metabolism of experimental hypercholesterolemic rats. J Nutr. 1973 Jan;103(1):88-92. PubMed PMID: 4682454. 19: Uchino H, Itokawa Y. [Studies on nutritional value of S-methylcysteine sulfoxide. I. Effect of increased dietary S-methylcysteine sulfoxide on growth and tissues in rats]. Nihon Eiseigaku Zasshi. 1972 Jun;27(2):248-52. Japanese. PubMed PMID: 4677394. 20: Kumari K, Augusti KT. Antidiabetic effects of S-methylcysteine sulphoxide on alloxan diabetes. Planta Med. 1995 Feb;61(1):72-4. PubMed PMID: 7700997.