Selenomethionine

Base Information

• Chemical Name: Selenomethionine
• CAS No.: 1464-42-2
• Deprecated CAS: 2578-28-1
• Molecular Formula: C₅H₁₁NO₂Se
• Molecular Weight: 196.108
• Hs Code.: 2931909000
• European Community (EC) Number: 215-977-0,678-482-2
• NSC Number: 724226,172801
• UNII: J9V40V4PKZ
• DSSTox Substance ID: DTXSID7040609
• Nikkaji Number: J13.127J
• Wikipedia: Selenomethionine
• Wikidata: Q415925
• NCI Thesaurus Code: C826
• Metabolomics Workbench ID: 123525
• ChEMBL ID: CHEMBL1474517
• Mol file: 1464-42-2.mol

Synonyms:Butanoic acid, 2-amino-4-(methylseleno)-;Radioselenomethionine;Se 75, Selenomethionine;Selenomethionine;Selenomethionine Hydrochloride, (S)-Isomer;Selenomethionine Se 75;Selenomethionine, (+,-)-Isomer;Selenomethionine, (R)-Isomer;Selenomethionine, (S)-Isomer;Sethotope

Chemical Property of Selenomethionine

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 6.45E-05mmHg at 25°C
• Melting Point: 267-269 ºC
• Boiling Point: 320.8°Cat760mmHg
• PKA: 2.26±0.10(Predicted)
• Flash Point: 147.8°C
• PSA: 63.32000
• Density: g/cm³
• LogP: 0.65930
• Storage Temp.: −20°C
• Solubility.: almost transparency in 1mol/L HCl
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 196.99550
• Heavy Atom Count: 9
• Complexity: 97

Purity/Quality:

98%,99%, ^*data from raw suppliers

Selenomethionine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C[Se]CCC(C(=O)O)N
• Recent ClinicalTrials: Seleno-L Methionine (SLM)-Axitinib-Pembrolizumab
• Description: Preparation of 4'-Bromoacetanilide from Acetanilide. Principle: Aromatic compounds can be conveniently brominated by the use of brominating agent, which is normally a solution of bromine in acetic acid. Bromination of activated aromatic compounds usually give 2, 4, 6-tribromo derivatives while moderately activating group like anilide give preferably the para bromo product. Reaction: Procedure: Dissolve 0.5 g acetanilide in 0.6 ml glacial acetic acid and add 2.5 ml bromine solution in acetic acid (25% w/v). Shake the mixture for 1 h. After 1 h, pour the mixture on to crushed ice (20 g) with stirring. Filter the separated product and wash with cold water. Dry the product, record the practical yield and re-crystallize it. Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC (using toluene as a solvent). Selenomethionine is the major form of selenium in plant foods. Selenomethionine is identical to methionine, except that selenium replaces the sulfur atom. The selenium consumed as selenocysteine is broken down to form alanine and hydrogen selenide (H2Se). The breakdown pathway of selenomethion- ine is not clear. Although selenium does not occur to a great extent as selenite in foods, selenite is readily used as a source of the element by humans and animals. Selenium also occurs as selenate in foods such as beet leaves, garlic, and cabbage. DL-Selenomethionine is a selenium (Se) analogue of methionine in which sulfur is replaced with the trace element selenium. Selenomethionine (SeMet) can incorporate into proteins in place of methionine with no effects on protein structure and function, providing a mechanism for reversible Se storage in organs and tissues. Free selenium is incorporated into selenocysteine, an amino acid found in more than thirty selenoproteins including the glutathione peroxidases (GPx) enzymes, thioredoxin reductase (TR) and the iodothyronine deiodinase enzymes.
• Uses: contrast agent Selenium as selenite, DL-selenomethionine, and DL-selenocystine was equally effective in preventing liver necrosis, but factor 3 selenium was three times more effective than these forms (Burk, 1976; Schwarz and Foltz, 1958).
• Biological Functions: Most selenium in animal tissues is present as selenomethionine or selenocysteine. Selenomethionine, which cannot be synthesized by humans and is initially synthesized in plants, is incorporated randomly in place of methionine in a variety of proteins obtained from plant and animal sources. Selenium is present in varying amounts in these proteins, which are called selenium-containing proteins. Selenomethionine is not known to have a physiological function separate from that of methionine. Selenocysteine is present in animal selenoproteins that have been characterized (see below) and is the form of selenium that accounts for the biological activity of the element. In contrast to selenomethionine, there is no evidence that selenocysteine substitutes for cysteine in humans.

Technology Process of Selenomethionine

There total 6 articles about Selenomethionine 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:

dimethyl diselenide (7101-31-7) + (l)α-amino-γ-butyrolactone hydroiodide (127628-31-3,171736-85-9) → (d)selenomethionine (1464-42-2,2578-28-1,3211-76-5,13091-98-0) + (l)selenomethionine (1464-42-2,2578-28-1,3211-76-5,13091-98-0)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 2) DMF, 40 - 50 deg C;

Reference yield:

dimethyl diselenide (7101-31-7) + (l)α-amino-γ-butyrolactone hydroiodide (127628-31-3,171736-85-9) → (d)selenomethionine (1464-42-2,2578-28-1,3211-76-5,13091-98-0) + (l)selenomethionine (1464-42-2,2578-28-1,3211-76-5,13091-98-0)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 2) DMF, 40 - 50 deg C;

Reference yield:

methyl selenide (6486-05-1) + (l)α-amino-γ-butyrolactone (1192-20-7,2185-02-6,7686-01-3,51744-82-2) → (d)selenomethionine (1464-42-2,2578-28-1,3211-76-5,13091-98-0) + (l)selenomethionine (1464-42-2,2578-28-1,3211-76-5,13091-98-0)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 2) DMF, 40 - 50 deg C;

upstream raw materials:

dimethyl diselenide

(l)α-amino-γ-butyrolactone hydroiodide

methyl selenide

(l)α-amino-γ-butyrolactone

Refernces