S-adenosylmethionine

Base Information

• Chemical Name: S-adenosylmethionine
• CAS No.: 29908-03-0
• Deprecated CAS: 23095-97-8,28378-99-6,5134-37-2,86522-35-2,86866-89-9,2613-02-7,2613-02-7,28378-99-6,86522-35-2,86866-89-9
• Molecular Formula: C₁₅H₂₂N₆O₅S
• Molecular Weight: 398.443
• Hs Code.: 29349990
• European Community (EC) Number: 249-946-8
• UNII: 7LP2MPO46S,6EZ5466ZUX,K093C397UL
• DSSTox Substance ID: DTXSID6032019
• Wikipedia: S-Adenosyl_methionine
• Wikidata: Q27135598,Q27264758,Q27281766
• NCI Thesaurus Code: C100098
• RXCUI: 9504
• Metabolomics Workbench ID: 121951
• ChEMBL ID: CHEMBL1235831,CHEMBL1088977
• Mol file: 29908-03-0.mol

Synonyms:Ademetionine;AdoMet;FO 1561;FO-1561;FO1561;Gumbaral;S Adenosyl L Methionine;S Adenosylmethionine;S Adenosylmethionine Sulfate Tosylate;S Amet;S-Adenosyl-L-Methionine;S-Adenosylmethionine;S-Adenosylmethionine Sulfate Tosylate;SAM-e;Samyr

Chemical Property of S-adenosylmethionine

Chemical Property:

• Melting Point: 247-249oC
• PSA: 547.02000
• LogP: -0.26280
• Storage Temp.: -20°C
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 398.13723900
• Heavy Atom Count: 27
• Complexity: 527

Purity/Quality:

99%, ^*data from raw suppliers

S-Adenosyl-L-methionine ^*data from reagent suppliers

Safty Information:

• Statements: 49-23-34
• Safety Statements: 53-23-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[S+](CCC(C(=O)[O-])N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O
• Isomeric SMILES: C[S+](CC[C@@H](C(=O)[O-])N)C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)O
• Recent ClinicalTrials: S-Asenosyl-L-Methionine vs Placebo for Osteoarthritis of the Hands
• Recent EU Clinical Trials: SAMe as an epigenetic treatment of depression in people with childhood trauma, a double blind placebo-controlled trial
• description: S-Adenosyl-L-methionine (also called S-adenosyl methionine, S-adenosylmethionine, SAMe, or SAM-e in the United States or ademetionine in Europe, and also often abbreviated as SAM and AdoMet) is a chemical that is found naturally in the body. SAMe is sold in the United States as a dietary supplement. S-Adenosyl-L-methionine was discovered in the early 1950s. It’s made in the body from methionine, an amino acid found in foods. It has been found to regulate key functions in living cells. Abnormal levels of S-Adenosyl-L-methionine in the body have been reported in liver diseases and depression. This prompted researchers to investigate whether S-Adenosyl-L-methionine might be helpful in treating these conditions. The idea that S-Adenosyl-L-methionine might be helpful for osteoarthritis came from studies of S-Adenosyl-L-methionine for depression. Some of the participants in the depression studies who also had osteoarthritis said their joint symptoms improved when they took S-Adenosyl-L-methionine.
• Uses: white powder LOD 0.2%
• Therapeutic Function: Metabolic, Antiinflammatory

Technology Process of S-adenosylmethionine

There total 10 articles about S-adenosylmethionine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

L-methionine (63-68-3,26062-47-5,58576-49-1) + ATP (56-65-5,896506-78-8) → S-Adenosyl-L-methionine (14031-35-7,17176-17-9,29908-03-0,75044-81-4,78548-84-2,79647-17-9,91279-78-6) + 5'-Deoxy-5'-methylthioadenosine (2457-80-9)

Guidance literature:

With recombinant Methanocaldococcus jannaschii methionine adenosyltransferase; potassium chloride; magnesium chloride; In aq. buffer; at 65 ℃; for 4h; pH=8; Temperature; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/anie.201308272

Reference yield:

1-methylhexahydropyrylium tetrafluoroborate (6914-65-4) + S-(5'-adenosyl)-L-homocysteine (979-92-0) → S-Adenosyl-L-methionine (14031-35-7,17176-17-9,29908-03-0,75044-81-4,78548-84-2,79647-17-9,91279-78-6)

Guidance literature:

1-methylhexahydropyrylium tetrafluoroborate; S-(5'-adenosyl)-L-homocysteine; With sulfuric acid; trifluoroacetic acid; at 0 ℃;

In dichloromethane; water; Product distribution / selectivity;

Reference yield:

1-methyloxiranium tetrafluoroborate (20725-78-4) + S-(5'-adenosyl)-L-homocysteine (979-92-0) → S-Adenosyl-L-methionine (14031-35-7,17176-17-9,29908-03-0,75044-81-4,78548-84-2,79647-17-9,91279-78-6)

Guidance literature:

1-methyloxiranium tetrafluoroborate; S-(5'-adenosyl)-L-homocysteine; With sulfuric acid; trifluoroacetic acid; at 0 ℃;

In dichloromethane; water; Product distribution / selectivity;

upstream raw materials:

methyl iodide

S-(5'-adenosyl)-L-homocysteine

D-Glucose

L-methionine

Downstream raw materials:

N-Methylnicotinium

R-(+)-N'-methylnicotinium ion

R-(+)-N-methylnicotinium ion

retusin

Refernces

• 1、 Zhang, Zhengan,Mahanta, Nilkamal,Hudson, Graham A.,Mitchell, Douglas A.,Van Der Donk, Wilfred A.. "Mechanism of a Class C Radical S-Adenosyl- l -methionine Thiazole Methyl Transferase". . p. 18623 - 18631. Retrieved 2017/12/26.
• 2、 -. "Chemical Synthesis Of S-Adenosyl-L-Methionine With Enrichment Of (S,S)-Isomer". Page/Page column 4; 5. . Retrieved 2008/06/13.