Merck
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A2408

Sigma-Aldrich

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt

≥80% (HPLC), ≥80% (spectrophotometric assay)

Synonym(s):
AdoMet, SAM p-toluenesulfonate salt
Empirical Formula (Hill Notation):
C15H23N6O5S · C7H7O3S · xC7H8O3S
CAS Number:
Molecular Weight:
570.64 (free base basis)
PubChem Substance ID:
NACRES:
NA.32

Quality Level

biological source

synthetic (Organic)

assay

≥80% (HPLC)
≥80% (spectrophotometric assay)

form

powder

composition

p-Toluenesulfonate content, 1.6-4.4 mol/mol

color

white to off-white

solubility

H2O: 100 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(O[H])[C@](N([H])[H])([H])C([H])([H])C([H])([H])[S@+](C([H])([H])[H])C([H])([H])[C@@]([C@](O[H])([H])[C@@]1([H])O[H])([H])O[C@]1([H])N2C3=C(N=C2[H])C(N([H])[H])=NC([H])=N3.O=S(C4=C([H])C([H])=C(C([H])([H])[H])C([H])=C4[H])([O-])=O

InChI

1S/C15H22N6O5S.C7H8O3S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;1-6-2-4-7(5-3-6)11(8,9)10/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);2-5H,1H3,(H,8,9,10)/t7-,8+,10+,11+,14+,27?;/m0./s1

Inchi Key

VHPOFDUCFKOUHV-XKGORWRGSA-N

General description

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt is used for the treatment of depression, liver cirrhosis, cholestasis and degenerative joint disease.

Application

S-(5′-Adenosyl)-L-methionine p-toluenesulfonate salt has been used for cell proliferation assay. It has also been used for methylation assay.

Packaging

25, 100, 500 mg in poly bottle

Biochem/physiol Actions

Methyl donor; cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. It is also involved in regulating liver function, growth, and response to injury.
S-(5′-Adenosyl)-L-methionine (SAM) is anti-apoptotic in normal hepatocytes and normal colon epithelial cells but pro-apoptotic in liver human hepatocellular carcinoma (HCC), HepG2 cells and colon cancer cells.

Caution

This material is unstable at room temperature.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More documents

Quotes and Ordering

Le Thanh Mai Pham et al.
Enzyme and microbial technology, 82, 66-73 (2015-12-18)
Using bioinformatic homology search tools, this study utilized sequence phylogeny, gene organization and conserved motifs to identify members of the family of O-methyltransferases from lignin-degrading fungus Phanerochaete chrysosporium. The heterologous expression and characterization of O-methyltransferases from P. chrysosporium were studied.
Allison B Norvil et al.
Nucleic acids research, 48(7), 3761-3775 (2020-03-04)
We have previously shown that the highly prevalent acute myeloid leukemia (AML) mutation, Arg882His, in DNMT3A disrupts its cooperative mechanism and leads to reduced enzymatic activity, thus explaining the genomic hypomethylation in AML cells. However, the underlying cause of the
Dietary supplement S-adenosyl-L-methionine (AdoMet) effects on plasma homocysteine levels in healthy human subjects: a double-blind, placebo-controlled, randomized clinical trial
Thompson MA, et al.
Journal of Alternative and Complementary Medicine (New York, N.Y.), 15(5), 523-529 (2009)
Lupus autoimmunity altered by cellular methylation metabolism
Yang ML, et al.
Autoimmunity, 46(1), 21-31 (2013)
Negative regulation of interferon-induced transmembrane protein 3 by SET7-mediated lysine monomethylation
Shan Z, et al.
The Journal of biological chemistry, 288(49), 35093-35103 (2013)

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