L-(+)-Selenomethionine supplier

Name
L-(+)-Selenomethionine
EINECS 608-705-0
CAS No. 3211-76-5
Article Data16
CAS DataBase
Density
Solubility H₂O: 50 mg/mL
Melting Point 265 °C
Formula C₅H₁₁NO₂Se
Boiling Point 320.78 °C at 760 mmHg
Molecular Weight 196.108
Flash Point 147.803 °C
Transport Information UN 3283 6.1/PG 2
Appearance white to off-white powder
Safety 20/21-28-45-60-61-28A
Risk Codes 23/25-33-50/53
Molecular Structure
Hazard Symbols T, N
Synonyms Butanoic acid,2-amino-4-(methylseleno)-, (S)-;Butyric acid, 2-amino-4-(methylselenyl)-, L-(8CI);L-Selenomethionine;Seleno-L-methionine;Selenomethionine;
PSA 63.32000
LogP 0.65930

Synthetic route

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

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.5h; Ambient temperature;	96%

: 37773-10-7
sodium methylselenide

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

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
In methanol; ethanol at 45℃; for 9h; Solvent; Temperature; Inert atmosphere;	82%

: 77-78-1
dimethyl sulfate

: L,L-selenohomocystine

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
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%

: 917-54-4
methyllithium

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

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
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

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
(i) aq. H2SO4, AcOEt, (ii) HBr, HSCH2CH2OH, AcOH; Multistep reaction;

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

: 74-88-4
methyl iodide

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
(i) Na, liq. NH3, (ii) /BRN= 969135/, NH4Cl; Multistep reaction;

: Lithium; 2-acetylamino-4-methylselanyl-butyrate

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
at 39℃; aminoacylase;

: 174463-50-4
2-Acetylamino-4-methylselanyl-butyric acid

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
With acylase from Aspergillus oryzae; water at 20 - 37℃;

: N-Acetylseleno-L-methionine

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
With pig kidney acylase I In phosphate buffer at 37℃; for 0.166667h; pH=7.4; Enzyme kinetics; Deacetylation;

: 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

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
With E. coli cobalamin-independent methionine synthase (2-649) Enzyme kinetics; Methylation;

: 29475-60-3
L-selenohomocysteine

methylcobalamin: methylcobalamin

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
With E. coli cobalamin-dependent methionine synthase (2-649) Enzyme kinetics; Methylation;

: 2578-28-1
seleno-DL-methionine

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
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

: 109276-72-4
L-benzyl N-t-butoxycarbonylselenomethioninate

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
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

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
In methanol; water at 20℃; for 0.166667h; Alkaline conditions;

: 2185-03-7
L-homoserine lactone hydrochloride

: 37773-10-7
sodium methylselenide

: 3211-76-5
Seleno-L-methionine

Conditions

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

: C13H17NO4Se

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
With hydrogen bromide In tetrahydrofuran; 1,4-dioxane Inert atmosphere; Green chemistry;	8.99 g

: 67-68-5
dimethyl sulfoxide

: L,L-selenohomocystine

: 3211-76-5
Seleno-L-methionine

Conditions

Conditions	Yield
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

: 24424-99-5
di-tert-butyl dicarbonate

: 3211-76-5
Seleno-L-methionine

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

Conditions

Conditions	Yield
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;

: 3211-76-5
Seleno-L-methionine

: 70-34-8
2,4-Dinitrofluorobenzene

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

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran at 20 - 40℃; for 9h;	90%

: 64-18-6
formic acid

: 3211-76-5
Seleno-L-methionine

: N-formyl selenomethionine

Conditions

Conditions	Yield
With acetic anhydride for 1h;	88%

: 3211-76-5
Seleno-L-methionine

: L-selenomethionine Se-oxide

Conditions

Conditions	Yield
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

: 3211-76-5
Seleno-L-methionine

: 2-(acetylmethylseleno)benzoyl chloride

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

Conditions

Conditions	Yield
In acetone at 0℃; for 8.5h;	85%

: 108-30-5
succinic acid anhydride

: 3211-76-5
Seleno-L-methionine

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

Conditions

Conditions	Yield
With sulfuric acid In water; ethyl acetate for 1h; Heating / reflux;	84.14%

: 3211-76-5
Seleno-L-methionine

: N-carbamoyl L-selenomethionine

Conditions

Conditions	Yield
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%

: 3211-76-5
Seleno-L-methionine

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

: L-selenomethionine methyl ester hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 18h;	83%

: copper(II) nitrate trihydrate

: 3211-76-5
Seleno-L-methionine

: Cu(L-selenomethionine)2

Conditions

Conditions	Yield
With sodium hydroxide In water pH=6;	78%

: 699-08-1
1-ethoxy-4-iodobenzene

: 3211-76-5
Seleno-L-methionine

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

Conditions

Conditions	Yield
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%

: 112-16-3
n-dodecanoyl chloride

: 3211-76-5
Seleno-L-methionine

: N-lauroyl-L-selenomethionine

Conditions

Conditions	Yield
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%

: 3211-76-5
Seleno-L-methionine

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

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

Conditions

Conditions	Yield
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%

: 3211-76-5
Seleno-L-methionine

: 5'-chloro-5'-deoxyadenosine

: Selenoadenosylhomocysteine

Conditions

Conditions	Yield
at 50℃; for 24h; Cooling with acetone-dry ice; Inert atmosphere;	74%

: 3211-76-5
Seleno-L-methionine

: 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

Conditions

Conditions	Yield
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%

: 112-77-6
(Z)-9-octadecenoyl chloride

: 3211-76-5
Seleno-L-methionine

: N-oleoyl-L-selenomethionine

Conditions

Conditions	Yield
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%

: 3211-76-5
Seleno-L-methionine

: 29475-60-3
L-selenohomocysteine

Conditions

Conditions	Yield
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;

: 3211-76-5
Seleno-L-methionine

: 67-63-0
isopropyl alcohol

: L-selenomethionine isopropyl ester

Conditions

Conditions	Yield
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%

: 3211-76-5
Seleno-L-methionine

: 104-88-1
4-chlorobenzaldehyde

: 75-64-9
tert-butylamine

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

Conditions

Conditions	Yield
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%

...Expand

: 3211-76-5
Seleno-L-methionine

: 1184-57-2
methylmercury(II) hydroxide

: methylmercury-L-selenomethioninate

Conditions

Conditions	Yield
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%

: 3211-76-5
Seleno-L-methionine

: 100-39-0
benzyl bromide

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

B: 29475-60-3
L-selenohomocysteine

Conditions

Conditions	Yield
With hydrogenchloride In water at 100℃; for 12h;	A 7% B 38%

...Expand

: 3211-76-5
Seleno-L-methionine

: 75-26-3
isopropyl bromide

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

Conditions

Conditions	Yield
With hydrogenchloride In water at 100℃; for 12h;	9%
With hydrogenchloride In water at 100℃; for 12h;	9%

: 3211-76-5
Seleno-L-methionine

: 100-39-0
benzyl bromide

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

Conditions

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

L-(+)-Selenomethionine Specification

The IUPAC name of L-(+)-Selenomethionine is (2S)-2-amino-4-methylselanylbutanoic acid. With the CAS registry number 3211-76-5, it is also named as Selenomethionine. The product's categories are Amino Acid Derivatives; Methionine [Met, M]; Amino Acids; Antioxidant; Biochemistry; Biological-modified Amino Acids; Classes of Metal Compounds; Se (Selenium) Compounds; Semimetal Compounds. Besides, it is white to off-white powder, which should be stored in closed, cool and dry place at -20 °C. In addition, its molecular formula is C₅H₁₁NO₂Se and molecular weight is 196.11.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5):; (4)ACD/LogD (pH 7.4):; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.32 Å²; (13)Flash Point: 147.803 °C; (14)Melting Point: 265 °C; (15)Solubility: H₂O: 50 mg/mL; (16)alpha: 18 °(c=1, 1N HCl); (17)Enthalpy of Vaporization: 61.843 kJ/mol; (18)Boiling Point: 320.78 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of L-(+)-Selenomethionine: this chemical can be prepared by 2-tert-Butoxycarbonylamino-4-methylselanyl-butyric acid.

This reaction needs trifluoroacetic acid and CH₂Cl₂ at ambient temperature for 30 min. The yield is 96 %.

Uses of L-(+)-Selenomethionine: this chemical can be used to incorporate into proteins in place of methionine aids the structure elucidation of proteins by X-ray crystallography using multi-wavelength anomalous diffraction (MAD). It also can be used as food additive.

When you are using this chemical, please be cautious about it as the following: it is toxic by inhalation and if swallowed. It is also danger of cumulative effects. When using, do not smoke, eat or drink. And after contact with skin, wash immediately with plenty of soap-suds. Moreover, it is very toxic to aquatic organisms that may cause long-term adverse effects in the aquatic environment. This material and its container must be disposed of as hazardous waste. Additionally, please avoid release to the environment. Refer to special instructions / safety data sheets. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: C[Se]CC[C@@H](C(=O)O)N
(2)InChI: InChI=1/C5H11NO2Se/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
(3)InChIKey: RJFAYQIBOAGBLC-BYPYZUCNBA

Product Name

L-(+)-Selenomethionine

Synthetic route

L-(+)-Selenomethionine Specification

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