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

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

Uses

Used in Animal Feed Industry:
DL-Methionine is used as a dietary supplement in animal feed to ensure adequate levels of methionine, which is essential for the growth and development of animals. It helps in maintaining proper growth, feathering, and egg production in poultry and swine.
Used in Human Food Industry:
DL-Methionine is utilized in the human food industry to enhance the nutritional value of various food products. Its presence in the diet contributes to the synthesis of proteins and other organic molecules required for optimal health.
Used in Pharmaceutical Industry:
DL-Methionine is employed in the pharmaceutical industry for its role as a precursor to important metabolites, such as glutathione, an antioxidant that helps protect cells from oxidative stress, and S-adenosylmethionine, a precursor for neurotransmitters that play a crucial role in brain function and mood regulation.
Used in Cosmetic Products:
In the cosmetic industry, DL-Methionine is used for its potential benefits to skin health. Its antioxidant properties may help protect the skin from environmental damage, and its role in the synthesis of proteins can contribute to the maintenance of healthy skin structure and function.

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

• 53751-63-6 Carbonyl-bis(L-methionin) 
• 7349-78-2 DD/LL/LD/DL-methionylmethionine 
• 3198-47-8 α-amino-γ-methylmercapto-butyronitrile 
• 81085-35-0 (E)-4-methylsulfanylbut-2-enoic acid 
• 110637-61-1 N-allyloxycarbonyl-methionine 
• 17773-41-0 2-hydroxy-4-(methylthio)butyronitrile 
• 74-90-8 hydrogen cyanide 
• 3268-49-3 3-(methylsulfenyl)propanal 
• 19298-72-7 DL-methionine amide 
• 74-93-1 methylthiol 
• 56512-51-7 2-amino-3-butenoic acid 
• 4471-04-9 N-carboxyl-2-aminobutyrolactone 
• 5188-07-8 sodium thiomethoxide 
• 1192-20-7 2-aminobutyrolactone 

Downstream Products

• 5464-44-8 1,3-dihydro-1,3-dioxo-α(CH2CH2SCH3)-2H-isoindole-2-acetate 
• 2766-51-0 (3-amino-3-carboxy-propyl)-dimethyl sulfonium ; bromide 
• 1655-53-4 N-(2,4-dinitro-phenyl)-methionine 
• 1017-76-1 S-benzyl homocysteine 
• 123-41-1 cholin hydroxide 
• 36963-02-7 3,6-bis[2-(methylthio)ethyl]-2,5-piperazinedione 
• 123529-85-1 N-phenoxyacetyl-DL-methionine 
• 31414-30-9 N-[(4-chloro-phenoxy)-acetyl]-DL-methionine 
• 73927-14-7 (+/-)-(3-amino-3-carboxy-propyl)-dimethyl sulfonium ; methyl sulfate 
• 62625-13-2 NSC87887 
• 369-16-4 N-trifluoroacetyl-DL-methionine 
• 65054-84-4 4-Methylsulfanyl-2-(3-trifluoromethyl-benzoylamino)-butyric acid 
• 93737-08-7 N'-(N-Methoxycarbonyl-DL-methionyl)-N,N-diaethyl-p-phenylendiamin 
• 27844-10-6 TMS-DL-Met-OTMS 

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 PRODUCING METHIONINE

An object of the present invention to provide a method for producing methionine with consideration given to the environment. The production method of the present invention comprises a removal step of blowing an inert gas into a liquid containing 5-(2-methylmercaptoethyl)hydantoin and thereby diffusing ammonia remaining in the liquid to obtain an emission gas containing the ammonia, and a recovery step of bringing the emission gas into contact with a washing liquid to recover ammonia contained in the emission gas.

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.

PROCESS FOR THE PREPARATION OF METHIONINE

The present invention relates to a process for the preparation of methionine comprising the step of contacting a solution or suspension comprising 2-amino-4-(methylthio)butanenitrile and/or 2-amino- 4-(methylthio)butaneamide with water in the presence of a catalyst to give a methionine comprising mixture, wherein the catalyst comprises CeO2 comprising particles, wherein the CeO2 comprising particles have a BET surface area of from 175 to 300 +/- 10% m2/g measured according to DIN ISO 9277-5 (2003), a mean maximum Feret diameter xFmax, mean of from 3 +/- 10% to 40 +/- 10% nm and a mean minimum Feret diameter xFmin, mean of from 2 +/- 10% to 30 +/- 10% nm, both measured according to DIN ISO 9276-6 (2012).

SALT-FREE PRODUCTION OF METHIONINE FROM METHIONINE NITRILE

The invention refers to the use of a particulate catalyst containing 60.0 to 99.5 wt.% ZrO2 stabilised with an oxide of the element Hf and at least one oxide of the element M, wherein M = Ce, Si, Ti, or Y, for the hydrolysis reaction of methionine amide to methionine, wherein the median particle size x50 of the particulate catalyst is in the range of from 0.8 to 9.0 mm, preferably of from 1.0 to 7.0 mm. The invention also refers to a process for preparing methionine comprising a step of contacting a solution or suspension comprising methionine amide and water with said particulate catalyst to provide a reaction mixture comprising methionine and/or its ammonium salt from which methionine can be isolated.

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.

PROCESS FOR THE PREPARATION OF D,L-METHIONINE

The invention relates to a single cycle process for preparing D,L-methionine from an alkali methioninate solution obtained by alkaline hydrolysis of 5-(2-methylmercaptoethyl)hydantoin, in which the D,L-methionine is obtained by neutralizing the alkali methioninate solution with carbon dioxide at elevated temperature and subsequently crystallizing D,L-methionine in the presence of seed crystals.

METHOD FOR PRODUCING alpha-AMINO ACID

The present invention relates to a method for producing a specified α-amino acid, the method including allowing a specified α-amino acid amide and water to react with each other in the presence of a zirconium compound which contains zirconium and at least one metal element selected from the group consisting of lithium, nickel, copper, zinc, cesium, barium, hafnium, tantalum, cerium, and dysprosium.

METHOD FOR PRODUCING METHIONINE AND/OR 2-HYDROXY-4-(METHYLTHIO) BUTANOIC ACID

An object of the invention is to provide a simple method for producing methionine and/or 2-hydroxy-4-(methylthio)butanoic acid at a high yield using 3-(methylthio)propionaldehyde as a raw material. An oxide catalyst containing cerium, 3-(methylthio)propionaldehyde, a compound containing cyanide ion, ammonia or a compound containing ammonium ion, and water are contacted with each other to produce methionine and/or 2-hydroxy-4-(methylthio)butanoic acid.

Economic and high-efficiency methionine preparation method

The invention provides an economic and high-efficiency methionine preparation method. The economic and high-efficiency methionine preparation method comprises the process of hydrolyzing of hydantoin intermediate, such as 5-(beta-methylthio-ethyl)hydantoin, and comprises the following specific steps of (1) mixing the hydantoin intermediate and a small amount of alkaline, sending into a reactor in phase I, and performing loop-open hydrolyzing reaction under the conditions of constant-power low-frequency ultrasonic wave and certain temperature; (2) continuously treating the liquid material in step (1) in a reactor in phase II, thoroughly hydrolyzing under the conditions of power same with the power in step (1) and higher-frequency ultrasonic wave and lower-temperature atmosphere, so as to obtain a saponification liquid of methionine; acidifying, so as to obtain the methionine. The economic and high-efficiency methionine preparation method has the advantages that the hydrolysis reaction efficiency of the hydantoin intermediate in the preparation process of the methionine is improved, and the reaction time is shortened by one time; the reaction temperature is greatly reduced, the hydrolysis yield rate is increased while the generation of side effect is reduced, and the requirement on the material of the reactor is lower.