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Home > Encyclopedia > L-Selenomethionine

L-Selenomethionine

L-Selenomethionine structure

L-Selenomethionine 

structure
  • CAS No:

    3211-76-5

  • Formula:

    C5H11NO2Se

  • Chemical Name:

    L-Selenomethionine

  • Synonyms:

    Butanoic acid,2-amino-4-(methylseleno)-,(2S)-;Butyric acid,2-amino-4-(methylselenyl)-,L-;Butanoic acid,2-amino-4-(methylseleno)-,(S)-;(2S)-2-Amino-4-(methylseleno)butanoic acid;Seleno-L-methionine;Selenomethionine;L-Selenomethionine;SelenoSource AF 2000;Selenomax;SelenoSource AF 600;SelenoSource AF;Vitaselenium;Prince Se Yeast 2000;(2S)-2-Azaniumyl-4-methylselanylbutanoate

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Description

L-SelenoMethionine is a major natural food-form of selenium.Target:The median lethal dose (LD50) of L-SelenoMethionine in rats given an intraperitoneal injection was determined to 4.25 mg Se/kg body and thus is comparable to that of selenite or selenate. In mice, the LD50 of L-SelenoMethionine was 8.8 ± 1.37 mg Se/kg, and the minimal lethal dose, 4.0 mg Se/kg, after intravenous injection.


Solid


L-selenomethionine is the L-enantiomer of selenomethionine. It is an enantiomer of a D-selenomethionine. It is a tautomer of a L-selenomethionine zwitterion.|Selenomethionine is a naturally occuring amino acid in some plant materials such as cereal grains, soybeans and enriched yeast but it cannot be synthesized from animals or humans. It can be produced from post-structural modifications. *In vivo*, selenomethionine plays an essential role in acting as an antioxidant, where it depletes reactive oxygen species (ROS) and aids in the formation and recycling of glutathione, another important antioxidant. In comparison to selenite, which is the inorganic form of selenium, the organic form of selenomethionine is more readily absorbed in the human body. Selenomethionin is used in biochemical laboratories where its incorporation into proteins that need to be visualized enhances the performance of X-ray crystallography.|L-Selenomethionine is the amino acid methionine with selenium substituting for the sulphur moiety. Methionine is an essential amino acid in humans, whereas selenium is a free-radical scavenging anti-oxidant, essential for the protection of various tissues from the damages of lipid peroxidation. As a trace mineral that is toxic in high doses, selenium is a cofactor for glutathione peroxidase, an anti-oxidant enzyme that neutralizes hydrogen peroxide. L-Selenomethionine is considered a safe, efficacious form of selenium and is readily bioavailable. Selenium may be chemoprotective for certain cancers, particularly prostate cancer. (NCI04)|Diagnostic aid in pancreas function determination.

L-Selenomethionine Basic Attributes

196.11

196.11

2017-001-1

964MRK2PEL

760370

DTXSID8046824

C2833

2922499990

Characteristics

63.3

0.65930

white to off-white powder

275 °C (decomp)

320.78°C at 760 mmHg

147.8±26.5 °C

18 ° (C=0.5, 2mol/L HCl)

H2O: 50 mg/mL

−20°C

18 º (c=1, 1N HCl)

137.67 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]|150 Ų [M-H]-

Safety Information

I; II; III

6.1

UN 3283 6.1/PG 2

3

23/25-33-50/53

20/21-28-45-60-61-28A

EK7713840

T,N

Stable under normal temperatures and pressures.

Missing Phrase - N15.00950417-P260-P304 + P340 + P312-P403 + P233

H301 + H331-H373-H410

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P314, P321, P330, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 95 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Butanoic acid, 2-amino-4-(methylseleno)-

L-Selenomethionine Use and Manufacturing

Methods of Manufacturing

Under a nitrogen atmosphere, 13.75 g of α-amino-γ-butyrolactone hydrochloride was mixed with 40 mL of DMF, Stir evenly. 15.2 g of sodium methyl selenate was dissolved in 20 mL of DMF, added to the above system and refluxed for 2 h. After the reaction was completed, the pH of the system was adjusted to 6.0 with an aqueous acetic acid solution to give a white solid, Solid water and ethanol mixed solution recrystallization, both L-selenomethionine. The total yield was 72.11percentChemical purity> 99percent, ee> 99percent.

Uses

A compound shown to increase expression of glutathione peroxidase

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:196.12
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:196.99550
Monoisotopic Mass:196.99550
Topological Polar Surface Area:63.3
Heavy Atom Count:9
Complexity:97
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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