Welcome to LookChem.com Sign In|Join Free

CAS

  • or

3211-76-5

Post Buying Request

3211-76-5 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

3211-76-5 Usage

Description

L-(+)-Selenomethionine, also known as Seleno-L-Methionine (SeMet), is an organic form of selenium found in Cupriavidus metallidurans. It is the L-enantiomer of selenomethionine and exists as a solid with unique chemical properties. L-(+)-Selenomethionine has been shown to increase the expression of glutathione peroxidase, which is an essential antioxidant enzyme in the body.

Uses

Used in Antioxidant Applications:
L-(+)-Selenomethionine is used as an antioxidant agent for its ability to increase the expression of glutathione peroxidase, which helps protect cells from oxidative stress and damage.
Used in Toxicity Studies:
L-(+)-Selenomethionine is used as a research compound in toxicity studies, such as those conducted on Japanese Medaka embryos, to understand its effects on various biological systems and potential environmental impacts.
Used in Selenium Status Studies:
L-(+)-Selenomethionine is used as a research compound in studies examining selenium status indicators, such as those conducted on pregnant long-tailed macaques (Macaca Fascicularis), to better understand the role of selenium in health and nutrition.
Used in Protein Labeling for Crystallography:
L-(+)-Selenomethionine is used as a protein labeling agent for single wavelength anomalous dispersion (SAD) phasing in crystallography. This application allows researchers to determine the three-dimensional structure of proteins, which is crucial for understanding their function and potential therapeutic applications.
Used in Pharmaceutical Industry:
L-(+)-Selenomethionine is used as an active pharmaceutical ingredient for the development of drugs targeting various health conditions, leveraging its antioxidant and selenium-related properties.
Used in Nutritional Supplements:
L-(+)-Selenomethionine is used as an ingredient in nutritional supplements to provide the essential trace element selenium, which is important for maintaining proper immune function, thyroid hormone metabolism, and DNA synthesis.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 3211-76-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,1 and 1 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3211-76:
(6*3)+(5*2)+(4*1)+(3*1)+(2*7)+(1*6)=55
55 % 10 = 5
So 3211-76-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

3211-76-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (S0442)  L-Selenomethionine  >98.0%(HPLC)(T)

  • 3211-76-5

  • 1g

  • 1,910.00CNY

  • Detail
  • TCI America

  • (S0442)  L-Selenomethionine  >98.0%(HPLC)(T)

  • 3211-76-5

  • 5g

  • 6,990.00CNY

  • Detail
  • USP

  • (1611955)  Selenomethionine  United States Pharmacopeia (USP) Reference Standard

  • 3211-76-5

  • 1611955-100MG

  • 4,588.74CNY

  • Detail

3211-76-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name L-selenomethionine

1.2 Other means of identification

Product number -
Other names Se-methionine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3211-76-5 SDS

3211-76-5Synthetic route

N-Boc-L-selenomethionine
45172-44-9

N-Boc-L-selenomethionine

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 0.5h; Ambient temperature;96%
sodium methylselenide
37773-10-7

sodium methylselenide

(3S)-(3-amino-3-carboxypropyl)dimethylsulfonium iodide
3493-11-6

(3S)-(3-amino-3-carboxypropyl)dimethylsulfonium iodide

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
In methanol; ethanol at 45℃; for 9h; Solvent; Temperature; Inert atmosphere;82%
dimethyl sulfate
77-78-1

dimethyl sulfate

L,L-selenohomocystine

L,L-selenohomocystine

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
Stage #1: L,L-selenohomocystine With sodium tetrahydroborate; ethanol at 30 - 45℃; for 5h; Inert atmosphere;
Stage #2: dimethyl sulfate at 25 - 30℃; for 3h; Temperature;
81.8%
methyllithium
917-54-4

methyllithium

α-amino-γ-bromobutyric acid methyl ester hydrochloride
15159-66-7

α-amino-γ-bromobutyric acid methyl ester hydrochloride

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
Stage #1: methyllithium; α-amino-γ-bromobutyric acid methyl ester hydrochloride With selenium; boric acid tributyl ester In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide at -78 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With methanol; sodium hydroxide In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide for 0.166667h; Temperature; Reagent/catalyst;
66%
(S)-2-Benzyloxycarbonylamino-4-methylselanyl-butyric acid; compound with dicyclohexyl-amine

(S)-2-Benzyloxycarbonylamino-4-methylselanyl-butyric acid; compound with dicyclohexyl-amine

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
(i) aq. H2SO4, AcOEt, (ii) HBr, HSCH2CH2OH, AcOH; Multistep reaction;
(2S)-2-amino-4-(benzylselanyl)butanoic acid
19635-25-7

(2S)-2-amino-4-(benzylselanyl)butanoic acid

methyl iodide
74-88-4

methyl iodide

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
(i) Na, liq. NH3, (ii) /BRN= 969135/, NH4Cl; Multistep reaction;
Lithium; 2-acetylamino-4-methylselanyl-butyrate

Lithium; 2-acetylamino-4-methylselanyl-butyrate

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
at 39℃; aminoacylase;
2-Acetylamino-4-methylselanyl-butyric acid
174463-50-4

2-Acetylamino-4-methylselanyl-butyric acid

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
With acylase from Aspergillus oryzae; water at 20 - 37℃;
N-Acetylseleno-L-methionine

N-Acetylseleno-L-methionine

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
With pig kidney acylase I In phosphate buffer at 37℃; for 0.166667h; pH=7.4; Enzyme kinetics; Deacetylation;
L-selenohomocysteine
29475-60-3

L-selenohomocysteine

N-[4-[[(2-amino-1,4,5,6,7,8,-hexahydro-4-oxo-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-L-glutamate

N-[4-[[(2-amino-1,4,5,6,7,8,-hexahydro-4-oxo-5-methyl-6-pteridinyl)methyl]amino]benzoyl]-L-glutamate

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
With E. coli cobalamin-independent methionine synthase (2-649) Enzyme kinetics; Methylation;
L-selenohomocysteine
29475-60-3

L-selenohomocysteine

methylcobalamin

methylcobalamin

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
With E. coli cobalamin-dependent methionine synthase (2-649) Enzyme kinetics; Methylation;
seleno-DL-methionine
2578-28-1

seleno-DL-methionine

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84.1 percent / 4 h / 15 - 30 °C
2: H2O, acylase from Aspergillus oryzae / 20 - 37 °C
View Scheme
L-benzyl N-t-butoxycarbonylselenomethioninate
109276-72-4

L-benzyl N-t-butoxycarbonylselenomethioninate

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / NaOH / dioxane; H2O / 0.5 h / Ambient temperature
2: 96 percent / trifluoroacetic acid / CH2Cl2 / 0.5 h / Ambient temperature
View Scheme
L-selenomethionine methyl ester hydrochloride

L-selenomethionine methyl ester hydrochloride

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
In methanol; water at 20℃; for 0.166667h; Alkaline conditions;
L-homoserine lactone hydrochloride
2185-03-7

L-homoserine lactone hydrochloride

sodium methylselenide
37773-10-7

sodium methylselenide

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 2h; Inert atmosphere; Reflux;n/a
C13H17NO4Se

C13H17NO4Se

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
With hydrogen bromide In tetrahydrofuran; 1,4-dioxane Inert atmosphere; Green chemistry;8.99 g
dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

L,L-selenohomocystine

L,L-selenohomocystine

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Conditions
ConditionsYield
Stage #1: L,L-selenohomocystine With sodium tetrahydroborate; ethanol at 35℃; for 5h; Inert atmosphere;
Stage #2: dimethyl sulfoxide at 45℃; for 1.5h; Temperature; Reagent/catalyst; Inert atmosphere;
43.4 g
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

N-Boc-L-selenomethionine
45172-44-9

N-Boc-L-selenomethionine

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine With sodium hydrogencarbonate In 1,4-dioxane; water for 0.333333h; Cooling with ice;
Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 20℃; for 13h; Cooling with ice;
98%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 20h;
With sodium hydrogencarbonate In 1,4-dioxane; water at 25℃;
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 12h;
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

N-(2,4-dinitrophenyl)seleno-L-methionine
919767-00-3

N-(2,4-dinitrophenyl)seleno-L-methionine

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran at 20 - 40℃; for 9h;90%
formic acid
64-18-6

formic acid

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

N-formyl selenomethionine

N-formyl selenomethionine

Conditions
ConditionsYield
With acetic anhydride for 1h;88%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

L-selenomethionine Se-oxide

L-selenomethionine Se-oxide

Conditions
ConditionsYield
With dihydrogen peroxide for 0.25h; cooling;85%
With Sprague-Dawley rat liver microsomes; NADPH; catalase In phosphate buffer for 0.333333h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents;
With dihydrogen peroxide In water
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

2-(acetylmethylseleno)benzoyl chloride

2-(acetylmethylseleno)benzoyl chloride

2-(2-acetonylselenobenzamide)-4-methylselenobutyric acid

2-(2-acetonylselenobenzamide)-4-methylselenobutyric acid

Conditions
ConditionsYield
In acetone at 0℃; for 8.5h;85%
succinic acid anhydride
108-30-5

succinic acid anhydride

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

(S)-4-(1-carboxy-3-(methylselanyl)propylamino)-4-oxobutanoic acid
918887-82-8

(S)-4-(1-carboxy-3-(methylselanyl)propylamino)-4-oxobutanoic acid

Conditions
ConditionsYield
With sulfuric acid In water; ethyl acetate for 1h; Heating / reflux;84.14%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

N-carbamoyl L-selenomethionine

N-carbamoyl L-selenomethionine

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine With potassium cyanate In water at 80 - 94℃; for 2h;
Stage #2: With hydrogenchloride In water at 20℃;
83.65%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

L-selenomethionine methyl ester hydrochloride

L-selenomethionine methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 18h;83%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

Cu(L-selenomethionine)2

Cu(L-selenomethionine)2

Conditions
ConditionsYield
With sodium hydroxide In water pH=6;78%
1-ethoxy-4-iodobenzene
699-08-1

1-ethoxy-4-iodobenzene

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

1-Ethoxy-4-methylselanyl-benzene
86297-06-5

1-Ethoxy-4-methylselanyl-benzene

Conditions
ConditionsYield
With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium dichloride In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 12h;78%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

N-lauroyl-L-selenomethionine

N-lauroyl-L-selenomethionine

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine With potassium hydroxide Sonication; Cooling with ice;
Stage #2: n-dodecanoyl chloride In tetrahydrofuran at 50℃; for 4h; pH=12; Temperature; pH-value; Cooling with ice;
77.34%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

5'-deoxy-5'-chloroadenosine
892-48-8

5'-deoxy-5'-chloroadenosine

Se-adenosyl-L-selenohomocysteine
4053-91-2

Se-adenosyl-L-selenohomocysteine

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine With ammonia; sodium at -35℃; for 1.25h; Inert atmosphere;
Stage #2: 5'-deoxy-5'-chloroadenosine In methanol at 50℃; for 24h; Inert atmosphere;
74%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

5'-chloro-5'-deoxyadenosine

5'-chloro-5'-deoxyadenosine

Selenoadenosylhomocysteine

Selenoadenosylhomocysteine

Conditions
ConditionsYield
at 50℃; for 24h; Cooling with acetone-dry ice; Inert atmosphere;74%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

5'-deoxy-5'-chloroadenosine
892-48-8

5'-deoxy-5'-chloroadenosine

(2R)-2-amino-4-((((2S,3S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)selanyl)butanoic acid

(2R)-2-amino-4-((((2S,3S,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)selanyl)butanoic acid

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine With ammonia; sodium Inert atmosphere; Cooling with acetone-dry ice;
Stage #2: 5'-deoxy-5'-chloroadenosine In methanol at 50℃; for 24h; Inert atmosphere;
74%
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

Seleno-L-methionine
3211-76-5

Seleno-L-methionine

N-oleoyl-L-selenomethionine

N-oleoyl-L-selenomethionine

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine With potassium hydroxide Sonication; Cooling with ice;
Stage #2: (Z)-9-octadecenoyl chloride In tetrahydrofuran at 25℃; for 2h; pH=9 - 10; Cooling with ice;
68.77%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

L-selenohomocysteine
29475-60-3

L-selenohomocysteine

Conditions
ConditionsYield
With ammonia; sodium at -78℃; for 1.33333h;62%
With ammonia; sodium at -80℃; for 0.833333h; demethylation;
With ammonia; sodium at -80℃; for 1h; Inert atmosphere; Darkness;
With ammonia; sodium at -60℃; for 1h;
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

isopropyl alcohol
67-63-0

isopropyl alcohol

L-selenomethionine isopropyl ester

L-selenomethionine isopropyl ester

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine; isopropyl alcohol With sulfuric acid at 0℃; for 48h; Heating / reflux;
Stage #2: With ammonia In water; isopropyl alcohol
52.61%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

tert-butylamine
75-64-9

tert-butylamine

(2S)-2-(((1-(tert-butyl)-1H-tetrazol-5-yl)(4-chlorophenyl)methyl)amino)-4-(methylselanyl)butanoic acid

(2S)-2-(((1-(tert-butyl)-1H-tetrazol-5-yl)(4-chlorophenyl)methyl)amino)-4-(methylselanyl)butanoic acid

Conditions
ConditionsYield
Stage #1: Seleno-L-methionine; 4-chlorobenzaldehyde In methanol at 20℃; for 0.166667h; Ugi Condensation;
Stage #2: tert-butylamine With sodium azide In methanol at 20℃; for 12h; Ugi Condensation;
51%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

methylmercury(II) hydroxide
1184-57-2

methylmercury(II) hydroxide

methylmercury-L-selenomethioninate

methylmercury-L-selenomethioninate

Conditions
ConditionsYield
With HNO3 In water byproducts: Se; Se-compound added to H2O, pH adjusted by HNO3 to 0.5, CH3HgOH added, stirred for 3.5 h; filtered, solvent evapd. in vac., kept under Ar at 4°C; elem. anal.;49%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

benzyl bromide
100-39-0

benzyl bromide

A

(2S)-2-amino-4-(benzylselanyl)butanoic acid
19635-25-7

(2S)-2-amino-4-(benzylselanyl)butanoic acid

B

L-selenohomocysteine
29475-60-3

L-selenohomocysteine

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 12h;A 7%
B 38%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

isopropyl bromide
75-26-3

isopropyl bromide

(2S)-2-amino-4-(propan-2-ylselanyl)butanoic acid
1601474-76-3

(2S)-2-amino-4-(propan-2-ylselanyl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 12h;9%
With hydrogenchloride In water at 100℃; for 12h;9%
Seleno-L-methionine
3211-76-5

Seleno-L-methionine

benzyl bromide
100-39-0

benzyl bromide

(2S)-2-amino-4-(benzylselanyl)butanoic acid
19635-25-7

(2S)-2-amino-4-(benzylselanyl)butanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 100℃; for 12h;7%

3211-76-5Relevant articles and documents

A new efficient synthesis of acetyltelluro- and acetylselenomethionine and their use in the biosynthesis of heavy-atom protein analogs

Karnbrock, Wilhelm,Weyher, Elisabeth,Budisa, Nediljko,Huber, Robert,Moroder, Luis

, p. 913 - 914 (1996)

-

Synthetic method of L-selenomethionine

-

Paragraph 0026-0039, (2020/02/17)

The invention discloses a synthetic method of L-selenomethionine, and belongs to the field of additives. The synthetic method comprises the following steps: A, a compound 1 and a compound 2 react in asolvent, and filtering and drying are carried out after a reaction is completed, and then a green solid compound 3 is obtained; and B, the compound 3 and sodium borohydride react in a protonic solvent for 1-10 h, after a reaction is completed, dimethyl sulfate is dropwise added to continue to react for 1-5 h, then quenching through acetic acid and filtering are conducted, and thus the L-selenomethionine is prepared. The synthetic method has the beneficial effects that 1, it is reported in the literature that the compound 1 is mild in condition and high in yield; 2, the compound 2 is mild in reaction condition, no highly toxic and foul sodium methyl selenide is generated, and labor protection and environmental protection are facilitated; 3, the compound 2 is easy to separate only through centrifugal spinning-filtration, and an obtained product is high in purity; and 4, adopted raw materials and reagents are all commercially available, in the preparation process of the L-selenomethionine, intermediates do not need to be separated, and operation is easy.

Method for synthesizing L L-(+)-selenomethionine (by machine translation)

-

Paragraph 0041; 0050-0052; 0058-0062; 0069-0071; 0078-0080, (2019/12/25)

The synthetic route disclosed L - (+) - by the invention has, L - (+) - the advantages that the raw materials, are easy to obtain, the reaction conditions are, mild, the reaction conditions are mild, the separation, and purification are easy, L - (+) - and the; method L - (+) - is easy, to separate and purify L - (+) - L - (+) - L - (+) . (by machine translation)

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 3211-76-5