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64306

Sigma-Aldrich

S-Methyl methanethiosulfonate

purum, ≥98.0% (GC)

Synonym(s):

S-Methyl thiomethanesulfonate, MMTS

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About This Item

Linear Formula:
CH3SO2SCH3
CAS Number:
Molecular Weight:
126.20
Beilstein:
1446059
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

Assay

≥98.0% (GC)

refractive index

n20/D 1.513 (lit.)
n20/D 1.513

bp

69-71 °C/0.4 mmHg (lit.)

solubility

chloroform: 750mg + 5 ml Chloroform mg/mL, colorless to light greenish-yellow

density

1.337 g/mL at 20 °C
1.337 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CSS(C)(=O)=O

InChI

1S/C2H6O2S2/c1-5-6(2,3)4/h1-2H3

InChI key

XYONNSVDNIRXKZ-UHFFFAOYSA-N

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Related Categories

Application


  • Modification of Thiol Enzymes: S-methyl methanethiosulfonate (MMTS) offers a unique method for the modification of thiol enzymes and redox-regulated proteins, providing potential applications in biochemical research focused on enzyme regulation and redox biology (Makarov et al., 2019).

  • Sensor Development for Protease Activity: S-methyl methanethiosulfonate is used as a blocking reagent on the structural transitions of papain-like cysteine proteases, which supports its utility in sensor development, allowing for the detection and analysis of protease activity in various biological processes (Markovic et al., 2023).

  • Agricultural Pathogen Control: Research evaluating S-methyl methanethiosulfonate as a late blight inhibitor highlights its potential as a broad-range toxin against plant pathogens, suggesting applications in agriculture for the management of crop diseases (Joller et al., 2020).

Caution

may discolor to yellow on storage

Other Notes

Methylsulfenylating agent with many applications; For the α-methylsulfenylation of cyclic ketones; Methyl disulfides from thiols; selective, reversible inactivation of enzymes

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Lot/Batch Number

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    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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  5. What is the solubility of Product 64306, S-Methyl methanethiosulfonate?

    Product 64306, S-Methyl methanethiosulfonate, is practically insoluble in water. It is soluble in methylene chloride. Several references do report that S-Methyl methanethiosulfonate is soluble in isopropanol at a 200mM concentration.  References are provided below: 1.  Yan, W., et al., "Quantitative Proteomic Analysis to Profile Dynamic Changes in the Spatial Distribution of Cellular Proteins", in Methods in Molecular Biology, Vol. 432: Organelle Proteomics, pp. 389-401 (Humana Press, 2008).2.  Sadowski, P.G., et al., Quantitative proteomic approach to study subcellular localization of membrane proteins.  Nature Protocols, 1, 1778-1789 (2006).

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P. Laszlo et al.
The Journal of Organic Chemistry, 49, 2281-2281 (1984)
D. Scholz
Synthesis, 944-944 (1983)
Anna-Riikka Karala et al.
Antioxidants & redox signaling, 9(4), 527-531 (2007-02-07)
S-Methyl methanethiosulfonate (MMTS) is a reagent used to trap the natural thiol-disulfide state of the proteins. The efficiency of trapping mixed disulfides in vivo has been found to be higher for MMTS than for the more commonly used N-ethylmaleimide. MMTS
W H Briggs et al.
Journal of agricultural and food chemistry, 48(11), 5731-5735 (2000-11-23)
Thiosulfinates (TSs) have been implicated as a principle source of the antiplatelet property of raw onion and garlic juice. The in vitro responses of human platelets to dosages of four TSs were measured using whole blood aggregometry and compared by
D J Smith et al.
Biochemistry, 14(4), 766-771 (1975-02-25)
New reagents for the temporary blocking of active or accessible sulfhydryl groups of enzymes have been developed. These reagents, which are either alkyl alkanethiolsulfonates or alkoxycarbonylalkyl disulfides, rapidly and quantitatively place various RS- groups on the sulfhydryls to generate mixed

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