ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Other amino acid derivatives L-Selenomethionine

L-Selenomethionine

Product NameL-Selenomethionine
CAS3211-76-5
MFC5H11NO2Se
MW196.11
EINECS608-705-0
MOL File3211-76-5.mol

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
Cosmetics Ingredients Functions	ANTIOXIDANT
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
Storage Class	6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials
Hazard Classifications	Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 STOT RE 2

MSDS

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

Usage And Synthesis

Chemical Properties

Solid

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

Uses

A compound shown to increase expression of glutathione peroxidase

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

2185-03-7

37773-10-7

3211-76-5

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

Preparation Products And Raw materials