59-51-8

Basic information

• Product Name: DL-Methionine
• Synonyms: Methilonin;Methionine, amorphous;Methionine, DL-;Hmet;Meonine;DL-Methioninum;Pedameth;2-amino-4-(methylsulfanyl)butanoic acid;(2S)-2-azaniumyl-4-methylsulfanyl-butanoate;(2R)-2-azaniumyl-4-methylsulfanyl-butanoate;Urimeth;Metione;2-amino-4-(methylthio)butanoic acid;Cynaron;Dyprin;Lobamine;(+-)-Methionine;Racemethionine [USAN];Neston;alpha-Amino-gamma-(methylthio)butyric acid;DL-2-Amino-4-(methylthio)-butyric acid;Acimetion;Banthionine;alpha-amino-gamma-methylmercaptobutyric acid;DL-2-Amino-4-(methylthio)butanoic acid;DL-2-Amino-4-methylthiobutyric acid;H-DL-Met-OH;Racemethionine
• CAS NO: 59-51-8
• Molecular Formula: C₅H₁₁NO₂S
• Molecular Weight: 149.21134
• EINECS: 200-432-1
• Mol File: 59-51-8.mol
• Article Data: 168

Chemical Properties

• Melting Point: 270-273℃
• Boiling Point: 306.9 °C at 760 mmHg
• Flash Point: 139.4 °C
• Appearance: white crystalline powder with a faint odor
• Density: 1.206 g/cm³
• Solubility: Sparingly soluble in water, very slightly soluble in alcohol. It dissolves in dilute acids and in dilute solutions of the alkali hydroxides
• Water Solubility: 2.9 g/100 mL (20℃)
• CAS DataBase Reference: DL-Methionine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Methionine(59-51-8)
• EPA Substance Registry System: DL-Methionine(59-51-8)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 59-51-8(Hazardous Substances Data)

Usage

General Description

DL-Methionine is an essential amino acid that is important for the synthesis of proteins and other organic molecules. It is used as a dietary supplement in animal feed to ensure adequate levels of methionine, which is essential for growth and development. DL-Methionine is a sulfur-containing amino acid that serves as a precursor for various important metabolites, including the antioxidant glutathione and the neurotransmitter precursor S-adenosylmethionine. It is commonly added to poultry and swine diets to maintain proper growth, feathering, and egg production. DL-Methionine is also used in the human food industry and in various pharmaceutical and cosmetic products.

InChI:InChI=1/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

Synthetic route

2-hydroxy-4-(methylthio)butyronitrile (17773-41-0) → DL-methionine (59-51-8)

Conditions	Yield
Stage #1: 2-hydroxy-4-(methylthio)butyronitrile With ammonia In water at 50℃; for 0.5h; Sealed tube; Stage #2: With cerium(IV) oxide In water at 75℃; for 2h; Reagent/catalyst; Temperature; Sealed tube;	100%
Multi-step reaction with 2 steps 1: NH3 / unter Druck 2: aqueous H2SO4 View Scheme
Multi-step reaction with 2 steps 1: ethanol; NH3 / 80 °C 2: aqueous H2SO4 View Scheme

O-acetyl homoserine → DL-methionine (59-51-8)

Conditions	Yield
	100%

DL-methionine amide (19298-72-7) → DL-methionine (59-51-8)

Conditions	Yield
With zirconium containing nickel oxide In water at 130℃; for 1h; Reagent/catalyst; Temperature;	100%
With water; potassium hydroxide at 120℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave;	100 %Chromat.

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione (13253-44-6) → DL-methionine (59-51-8)

Conditions	Yield
Stage #1: 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione With water; potassium carbonate at 120 - 160℃; Sonication; Stage #2: at 80 - 120℃; Reagent/catalyst; Sonication;	99.9%
Stage #1: 5-[2-(methylthio)ethyl]imidazolidine-2,4-dione With water; potassium hydroxide at 173 - 178℃; for 1h; Stage #2: With carbon dioxide; water at 20℃; Crystallization; Presence of polyvinyl alcohol;	97%
With water; potassium hydroxide at 120 - 173℃; pH=10.5;	53.6%

α-amino-γ-methylmercapto-butyronitrile (3198-47-8) → DL-methionine (59-51-8)

Conditions	Yield
With cerium(IV) oxide; water at 75℃; for 2h; Concentration; Reagent/catalyst;	97%
With ammonium hydroxide In water at 200℃; under 7500.75 Torr; for 20h; Pressure; Temperature; Inert atmosphere; Autoclave;	88.1%
Stage #1: α-amino-γ-methylmercapto-butyronitrile With ammonia; tetra(n-butyl)ammonium hydrogensulfate; calcium oxide In water at 180 - 190℃; under 18751.9 - 22502.3 Torr; for 5h; Stage #2: With carbon dioxide In water at 20℃; pH=8; Reagent/catalyst;	79.4%

methionine barium → DL-methionine (59-51-8)

Conditions	Yield
With carbon dioxide In water at 80 - 100℃; under 1500.15 Torr; for 0.5h; pH=6; Autoclave;	97%

Upstream product

• 454-29-5 2-amino-4-mercaptobutyric acid 
• 4727-41-7 dimethylsulfonioacetate 
• 408350-94-7 2-(2-methylsulfanyl-ethyl)-acetoacetic acid ethyl ester 
• 859200-50-3 (2-methylsulfanyl-ethyl)-malonic acid 
• 130629-26-4 ethyl 2-cyano-4-(methylthio)butyrate 
• 74-93-1 methylthiol 
• 5809-59-6 3-cyano-3-hydroxy-1-propene 
• 70982-53-5 (S)-2-amino-3-butenoic acid 
• 3198-47-8 α-amino-γ-methylmercapto-butyronitrile 
• 7647-01-0 hydrogenchloride 
• 17773-41-0 2-hydroxy-4-(methylthio)butyronitrile 
• 1017-76-1 S-benzyl homocysteine 
• 82102-39-4 acetylamino-(2-methylsulfanyl-ethyl)-malonic acid diethyl ester 
• 722497-10-1 2-acetylamino-2-cyano-4-methylsulfanyl-butyric acid ethyl ester 

Downstream Products

• 10332-17-9 DL-methionine methyl ester 
• 16118-36-8 methionine methyl ester hydrochloride 
• 5840-77-7 DL-methionine N-carboxyanhydride 
• 369-16-4 N-trifluoroacetyl-DL-methionine 
• 100568-90-9 N-[(2,4,5-trichloro-phenoxy)-acetyl]-DL-methionine 
• 4703-31-5 N-(N-benzoyl-glycyl)-methionine 
• 65055-24-5 N-salicyloyl-dl-methionine 
• 92702-71-1 optically inactive N-(2-phenyl-butyryl)-methionine 
• 5540-05-6 N-(N-benzyloxycarbonyl-glycyl)-methionine 
• 56830-84-3 5-(2-(methylthio)ethyl)-2-thioxoimidazolidin-4-one 
• 74-93-1 methylthiol 
• 348-67-4 D-methionine 
• 63-68-3 L-methionine 
• 1982-67-8 2-amino-4-(S-methylsulfonimidoyl)butanoic acid 

Relevant articles and documents

STORAGE-STABLE FORM OF 3-METHYLTHIOPROPIONALDEHYDE

A chemical compound of formula (I), and specific compositions including 3-methylthiopropionaldehyde, 3-methylthiopropane-1,1-diol, a compound of formula I and water, and processes for producing same and also the use of same may be used for the production of 2-hydroxy-4-(methylthio)butyronitrile, methionine hydantoin, methionine. Protected forms may be used for the storage and/or transport of 3-methylthiopropionaldehyde.

METHOD FOR MANUFACTURING METHIONINE

An object of the present invention is to provide a method for manufacturing methionine capable of achieving an improvement in ammonia removal efficiency. The manufacturing method of the present invention comprises a removal step of supplying a liquid containing a methionine salt, which is obtained by reacting 3-methylmercaptopropionaldehyde and hydrocyanic acid, or a compound obtained by reacting 3-methylmercaptopropionaldehyde and hydrocyanic acid, with carbon dioxide and ammonia to obtain a liquid containing 5-(2-methylmercaptoethyl)hydantoin and then hydrolyzing the 5-(2-methylmercaptoethyl)hydantoin, to a diffusion tower from an upper portion thereof while supplying a stripping gas to the diffusion tower from a lower portion thereof to remove ammonia contained in the liquid through stripping, and the stripping gas contains a process gas generated in a process of manufacturing methionine.

METHOD FOR PRODUCING METHIONINE

The present invention pertains to a method for producing methionine or salts or derivatives thereof from hydrogen cyanide (HCN), the method comprising a step of producing 2-hydroxy-4-(methylthio)butyronitrile (MMP-CN), or a crude product mixture comprising MMP-CN, by contacting a hydrogen cyanide (HCN) process gas mixture prepared according to the Andrussow process from methane, ammonia and oxygen, with 3-methylmercaptopropionaldehyde (MMP), wherein the HCN process gas mixture is obtained from the crude HCN process gas mixture by adjusting the amount of ammonia to between 20 % (v/v) and 60% (v/v) of the amount of the ammonia in the crude HCN process gas mixture.