L-Selenomethionine Chemical Properties

Melting point:

265 °C

alpha 

18 º (c=1, 1N HCl)

Boiling point:

320.8±37.0 °C(Predicted)

refractive index 

18 ° (C=0.5, 2mol/L HCl)

storage temp. 

-20°C

solubility 

H₂O: 50 mg/mL

form 

powder

pka

2.26±0.10(Predicted)

color 

white to off-white

Water Solubility 

soluble

Merck 

14,8441

InChI

InChI=1S/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

InChIKey

RJFAYQIBOAGBLC-BYPYZUCNSA-N

SMILES

C(O)(=O)[C@@H](N)CC[Se]C

LogP

0.152 (est)

CAS DataBase Reference

3211-76-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,N

Risk Statements 

23/25-33-50/53

Safety Statements 

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

RIDADR 

UN 3283 6.1/PG 2

WGK Germany 

3

RTECS 

EK7713840

F 

10

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309090

MSDS

• Language:English Provider:L-(+)-Selenomethionine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

L-Selenomethionine Usage And Synthesis

Chemical Properties

Solid

Uses

A compound shown to increase expression of glutathione peroxidase

Uses

L-Selenomethionine has been used:

• in toxicity studies in Japanese Medaka embryos
• to study its effects on selenium status indicators in pregnant long-tailed macaques (Macaca Fascicularis)
• to label proteins for single wavelength anomalous dispersion (SAD) phasing

Definition

ChEBI: The L-enantiomer of selenomethionine.

General Description

Seleno-L-Methionine (SeMet), an organic form of selenium is found in Cupriavidus metallidurans.

Biochem/physiol Actions

Seleno-L-Methionine (SeMet) is capable of repressing atopic dermatitis (AD)-like skin lesions. It can also prevent the expression of total immunoglobulin E (IgE) and interleukin 4 (IL-4). It can cause ecotoxicity as it is absorbed by fish through diet.

Synthesis

Under nitrogen protection, 13.75 g of L-homoserine lactone hydrochloride was mixed with 40 mL of N,N-dimethylformamide (DMF) and stirred until completely dissolved. Subsequently, 15.2 g of methyl selenate (CAS:37773-10-7) was dissolved in 20 mL of DMF and slowly added to the above reaction system. The reaction was heated and refluxed for 2 hours. Upon completion of the reaction, the pH of the reaction system was adjusted to 6.0 with aqueous acetic acid and a white solid was precipitated. The resulting solid was dissolved in a mixed solvent of water and ethanol for recrystallization to obtain L-selenomethionine. The total yield of this synthetic route was 72.11%, the chemical purity of the product was greater than 99% and the enantiomeric excess value (ee) was greater than 99%.

References

[1] Patent: CN106928110, 2017, A. Location in patent: Paragraph 0028; 0030

L-Selenomethionine(3211-76-5)Related Product Information

• Fmoc-Selenomethionine
• Selenomethionine[75Se]
• DL-Selenomethionine
• L-Selenomethionine
• D L-SELENOMETHIONINE 99+%,DL-SELENOMETHIONINE,DL-SELENOMETHIONINE-13C1 (METHYL-13C) 99
• BOC-DL-SELENOMETHIONINE
• N-ALPHA-FMOC-L-SELENOMETHIONINE,FMOC-L-SELENOMETHIONINE
• BOC-L-SELENOMETHIONINE
• FMOC-DL-SELENOMETHIONINE
• N-ACETYL-L-SELENOMETHIONIN
• D-SELENOMETHIONINE
• L-SELENOMETHIONINE BLEND
• DL-Selenomethionine-13C1 (methyl-13C1),DL-SELENOMETHIONINE-METHYL-13C1
• Selenium (as Selenomethionine)
• SELENOMETHIONINE, L-(+)-(RG)
• SELENOMETHIONINE-ENRICHEDSALMON
• L-Selenomethionine Blend, 5,000 μg/g
• SELENOMETHIONINE USP(CRM STANDARD)