63-68-3 Usage
Description
L-Methionine is a sulfur-containing essential L-amino acid that is important in many body functions. It is a colorless or white lustrous plate or a white crystalline powder with a slight, characteristic odor. L-Methionine is soluble in water, alkali solutions, and dilute mineral acids, slightly soluble in alcohol, and practically insoluble in ether. It is indispensable for normal growth and development of humans, other mammals, and avian species, and must be obtained from diet and food sources since it is unable to be biosynthesized in the body.
Used in Human Development and Therapy:
L-Methionine is used as an essential amino acid for human development and therapeutically acts as an antidote for acetaminophen poisoning.
Used in Chelating and Nutritional Supplements:
L-Methionine serves as a chelating agent for heavy metals, a flavoring agent, and a nutritional supplement for foods.
Used in Feed Additives and Animal Growth:
L-Methionine acts as a feed additive, improving feed quality, the utilization of native protein, and promoting animal growth. For example, DL-methionine can increase egg production in chickens, weight gain in pigs, and milk production in cows.
Used in Cosmetics:
L-Methionine is used as a texturizer in cosmetic creams and helps slow down and normalize oil gland sebum production.
Used in Biochemical Studies and Treatments:
L-Methionine is used for biochemical studies and nutritional supplements, and as adjunctive treatment for pneumonia, liver cirrhosis, and fatty liver.
Used in Hepatoprotection and Lipotropic Agent:
L-Methionine is used as a hepatoprotectant and acts as a lipotropic agent, preventing excess fat buildup in the liver.
Used in Vegetable Oil Enrichment and Single Cell Protein:
L-Methionine is also used in vegetable oil enrichment and as a single cell protein.
Used in Amino Acid Drugs and Nutritional Supplements:
L-Methionine is used in amino acid drugs and nutritional supplements, with the minimum daily requirement for an adult male being 13 milligrams per kilogram of body weight.
Used in Metabolic Precursor for Cysteine:
L-Methionine is accepted as the metabolic precursor for cysteine, with only the sulfur atom from methionine being transferred to cysteine.
Used in Treating Psychiatric Illnesses, Infertility, Liver Problems, Premenstrual Disorders, and Musculoskeletal Conditions:
L-Methionine helps the body produce SAMe (S-Adenosyl-L-methionine), which has been used to treat various conditions, including psychiatric illnesses, infertility, liver problems, premenstrual disorders, and musculoskeletal conditions.
Used in Ongoing Studies for Treating HIV/AIDS, Liver Damage, Parkinson's Disease, and Urinary Tract Infections:
Ongoing studies are being conducted to determine the effectiveness of L-Methionine for treating HIV/AIDS, liver damage, Parkinson's disease, and urinary tract infections.
Feed additives
L-Methionine is mainly used as feed nutritional supplements and one of the essential amino acids in the growth of animals, which is the "skeleton" amino acid in protein biosynthesis and main donor of methyl in animal body. L-Methionineplays a certain role in the process of synthesis of choline by adrenal hormone and fatty liver phospholipids during the process of metabolism of the animal in vivo. Lacking of L-Methioninein livestock and poultry will lead to poor development, weight loss, liver and kidney function decline, muscle atrophy, fur deterioration, etc.
L-Methionine is a sulfur amino acid and the second limiting essential amino acids for pigs. The utilization ratio of feed protein can be improved effectively if lysine and L-Methioninewere added in the feed appropriately. So the lysine and L-Methionineare called enhancer for protein feed. Naturally occurring L-Methioninehas two types: D type and L type two and their biological utilization rate is identical. Synthetic L-Methionineis a type DL compound of type D and type L. The biological potency of compound is the same as that of the single D or L-methionine. The appearance of DL methionine additive is white to pale yellow crystal or crystalline powder and insoluble in water and has slightly sweetness haste. The content of L-Methioninein feed of pig is generally from 0.05% to 0.1%.
L-Methionineas a nutritional supplement, the effect of the type L is the same as that of the type of DL (due to the type L transformed from the type DL). Feed additives; as the product and cysteine both belong to sulfur-containing amino acids, so a large amount of them exist in animal proteins. However, it belongs to limiting amino acids in plant proteins such as oats, rye, rice, corn, wheat, peanuts, soybeans, potatoes, spinach and other vegetable foods and the content is less than animal proteins.So it can be added to the above food to improve the balance of amino acids. In the past, sulphur-containing amino acids were thought to be only suitable for non-ruminants. But now the experiment has been proved that it is applicable to the non-ruminants. It is more suitable for chicken and pig feed. On the medical side, it can be used for infusion together with other amino acids. Also used as a culture medium during fermentation.
Pharmacodynamics
L-Methionineis a sulfur-containing amino acid. Choline is synthesized in vivo by the L-Methioninesupplying the required methyl. And choline is a component of lecithin. Lecithin is an essential material for the removal of fat from the liver and the deposition of fat in the liver. So L-Methioninealso has an effect in choline lipotropic. In addition, L-Methioninein vivo supplies sulfur to synthesize non-exogenous amino acid Cys. The latter has the function of detoxification. Therefore, this medicine is used for the liver lipotropic in clinical , which is Suitable for fatty liver and chronic hepatitis and liver cirrhosis with fat infiltration. Clinical L-Methioninecan also be used as an adjuvant therapy drug for alcohol and poisoning.
Amino acids
Amino acids are the constituent units of the protein and are the material basis of life. From as large as human beings to as small as microorganism, they are both made up of proteins. Proteins are composed of peptides and peptide chains of peptides are composed of amino acids. Different proteins are made of peptide chains which are composed of amino acids in a different order and length. Genetically related genes are actually different sequences of amino acid chains. At present, there are total 28 kinds of amino acids related to the human body. These 28 amino acids are arranged in a different order and different length of the chain to compose the various parts proteins of the body. Of these 28 kinds of amino acids, nine species (about 32%) are required by the direct supply of dietary protein amino acids. They cannot be synthesized by other amino acids in the proteins that are taken in by the human body. They are leucine, isoleucine, valine, lysine, methionine, tryptophan, threonine, phenylalanine and histidine.
L-Methionineis an essential amino acid. It can help break down fat. So it can prevent fatty liver, heart disease, cerebrovascular disease and renal disease. The synthesis of amino acids, such as cysteine and taurine, requires the assistance of methionine.
This amino acid can help to remove harmful substances, such as lead and other heavy metals. It can prevent muscle weakness and brittle hair. It is also good for the prevention and treatment of osteoporosis or chemical allergies. It is good for the treatment of rheumatic fever and pregnancy toxemia.
L-Methionineis still a potent antioxidant. The sulfur L-Methioninewhich contains can eliminate free radicals. The synthesis of nucleic acids, collagen and protein in the body all require methionine. It is also good to take L-Methioninefor women taking contraceptives. Because the level of histamine in the blood of patients with schizophrenia is much higher than that of normal people, it can reduce the level of histamine in the body. Therefore, it is effective for the treatment of schizophrenia. If the body's toxic substances increase, the need for L-Methioninealso increases. As the body can change the L-Methionineinto cysteine, and cysteine is the precursor of glutathione; and glutathione is the main toxic liver neutralizers. So it will be able to protect the liver from harm toxic substances.
Methionine-rich foods: beans, other legumes, eggs, fish, garlic, meat, onions and yogurt.
Toxicity
LD50 36g/kg (rat, oral)
Safe for food (FDA§172.320,2000)
Originator
Meonine ,Ives,US,1944
Production Methods
Numerous methods have been described for manufacture of
methionine, including hydrolysis of methionine amide )and 5-(bmethylmercaptoethyl)-
hydantoin.
Manufacturing Process
A 3-necked flask fitted with a stirrer, thermometer, gas inlet, dropping funnel, and brine-cooled reflux condenser was charged with 53 g (1.1 mol) methyl mercaptan and 0.35 g mercuric methyl mercaptide. After admitting 56 g (1.0mol) of acrolein during the course of 15 minutes with an inside temperature of
about 10°C, the temperature was allowed to rise spontaneously to 75°C, at
which point an ice bath was applied. There was no indication of further
reaction one hour after the addition of the acrolein. Distillation of the product
gave 71 g (yield 68%) of β-methylmercaptopropionaldehyde, as described in
US Patent 2,584,496.Then as described in US Patent 2,732,400, β-methylmercaptopropionaldehyde
(0.60 M) (56.5 g) is added to a stirred solution of sodium cyanide (0.66 M)
(32.4 g) and ammonium chloride (0.63 M) (33.7 g) in water (140 ml). The
temperature of the mixture rises to 49°C and is maintained at this point by
heat evolution for about 5 minutes when it slowly begins to fall. Methanol (50
ml) is added and the mixture is stirred for 4 hours as the temperature falls to
28°C (room temperature).After chilling to +12°C, additional methanol (35 ml) and a concentrated
aqueous ammoniun hydroxide solution (1.4 M) (100 ml) are added and
stirring is continued for 2 hours at a temperature maintained at from +5° to
+15°C. The organic layer is separated and solvent is stripped from the
aqueous layer at water aspirator pressure at a temperature below 40°C. The
residue is extracted several times with chloroform and the chloroform extracts
are combined with the separated oil. Chloroform is removed at water aspirator
pressure at a temperature below 35°C to leave crude α-amino-γmethylmercaptobutyronitrile (methionine nitrile) in 88% yield (68 g) as a
clear, somewhat viscous oil.The methionine nitrile (20 g) is dissolved in a solution prepared from 50 ml of
aqueous 5 N sodium hydroxide solution and 65 ml of ethanol. The solution is
then refluxed for 24 hours; ammonia is evolved. The solution is treated with
activated carbon, filtered, acidified with glacial acetic acid (17 ml), chilled to -
10°C and filtered to give crude product. This crude product is then slurried
with a solution made up of 20 ml of water and 20 ml of methanol, filtered at -
5° to +10°C and dried to give dl-methionine as white platelets.
Therapeutic Function
Lipotropic
Synthesis Reference(s)
Canadian Journal of Chemistry, 47, p. 3271, 1969 DOI: 10.1139/v69-542Synthetic Communications, 26, p. 3619, 1996 DOI: 10.1080/00397919608003774
Air & Water Reactions
Reacts with water, steam, and/or acids to produce toxic and flammable vapors of hydrogen sulfide . Water soluble . pH of 1% aqueous solution is 5.6-6.0.
Reactivity Profile
An organosulfide and amine derivative, carboxylic acid. Look at Reactive Groups 20 (organosulfides), 7 (amines), and 3 (carboxylic acids) may give indications about reactive tendencies. L-Methionine is an amino acid essential in human nutrition.
Health Hazard
ACUTE/CHRONIC HAZARDS: L-Methionine is dangerous when heated to decomposition; it emits dangerous and highly toxic fumes.
Fire Hazard
Flash point data for L-Methionine is not available, but L-Methionine is probably combustible.
Pharmaceutical Applications
Methionine is used in oral pharmaceutical formulations as a
flavoring agent.It has been included in parenteral formulations as
a pH controlling agent,and it has also been used experimentally
as an antioxidant with antibodies.Methionine is also used
therapeutically in oral tablets
Biochem/physiol Actions
L-Methionine serves as precursor for transmethylation and transsulphuration. Methionine adenosylation results in the formation of S-adenosyl-L-methionine (SAM). SAM serves as a methyl donor to a number of substances. This methylation is significantly associated with the immune system functioning. Thus, SAM deficiency causes severe combined immunodeficiencies. L-Methionine′s metabolic product, glutathione, is known to regulate immune response and has antiviral action.
Safety Profile
Mildly toxic by
ingestion and intraperitoneal routes. Human
mutation data reported. An experimental
teratogen. Experimental reproductive
effects. An essential sulfur-containing amino
acid. When heated to decomposition it emits
very toxic fumes of NOx and SOx.
Safety
Methionine is used in oral pharmaceutical formulations. The pure
form of methionine is mildly toxic by ingestion and by the IP route.
LD50 (rat, IP): 4.328 g/k
LD50 (rat, oral): 36 g/kg
storage
Methionine is sensitive to light and should be stored in a cool, dark
place.
Purification Methods
Crystallise L-methionine from aqueous EtOH. Also purify it by dissolving ~0.5g of amino acid in ~10mL of hot H2O, filtering, adjusting the pH to 5.8 with 5N HCl, collecting the solid after addition of ~20mL of EtOH. It is recrystallised by dissolving in H2O and adding EtOH. It sublimes at 197-208o/0.3mm with 99.8% recovery and unracemised [Gross & Gradsky J Am Chem Soc 77 1678 1955]. [Milne & Peng J Am Chem Soc 79 647 1957, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2125-2152 1961, Beilstein 4 IV 3189.]
Incompatibilities
Methionine is incompatible with strong oxidizing agents.
Regulatory Status
Included in the FDA Inactive Ingredients Database (oral tablets).
Included in parenteral preparations (injection solutions; powders
for reconstitution) licensed in the UK.
Check Digit Verification of cas no
The CAS Registry Mumber 63-68-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 3 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 63-68:
(4*6)+(3*3)+(2*6)+(1*8)=53
53 % 10 = 3
So 63-68-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
63-68-3Relevant articles and documents
Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography
Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong
supporting information, p. 390 - 398 (2021/01/13)
Separation of racemic mixtures is of great importance and interest in chemistry and pharmacology. Porous materials including metal-organic frameworks (MOFs) have been widely explored as chiral stationary phases (CSPs) in chiral resolution. However, it remains a challenge to develop new CSPs for reversed-phase high-performance liquid chromatography (RP-HPLC), which is the most popular chromatographic mode and accounts for over 90% of all separations. Here we demonstrated for the first time that highly stable Zr-based MOFs can be efficient CSPs for RP-HPLC. By elaborately designing and synthesizing three tetracarboxylate ligands of enantiopure 1,1′-biphenyl-20-crown-6, we prepared three chiral porous Zr(IV)-MOFs with the framework formula [Zr6O4(OH)8(H2O)4(L)2]. They share the same flu topological structure but channels of different sizes and display excellent tolerance to water, acid, and base. Chiral crown ether moieties are periodically aligned within the framework channels, allowing for stereoselective recognition of guest molecules via supramolecular interactions. Under acidic aqueous eluent conditions, the Zr-MOF-packed HPLC columns provide high resolution, selectivity, and durability for the separation of a variety of model racemates, including unprotected and protected amino acids and N-containing drugs, which are comparable to or even superior to several commercial chiral columns for HPLC separation. DFT calculations suggest that the Zr-MOF provides a confined microenvironment for chiral crown ethers that dictates the separation selectivity.
Motobamide, an Antitrypanosomal Cyclic Peptide from a Leptolyngbya sp. Marine Cyanobacterium
Iwasaki, Arihiro,Jeelani, Ghulam,Kurisawa, Naoaki,Matsubara, Teruhiko,Nozaki, Tomoyoshi,Sato, Toshinori,Suenaga, Kiyotake,Suzuki, Ryota,Takahashi, Hiroki
, p. 1649 - 1655 (2021/05/29)
Motobamide (1), a new cyclic peptide containing a C-prenylated cyclotryptophan residue, was isolated from a marine Leptolyngbya sp. cyanobacterium. Its planar structure was established by spectroscopic and MS/MS analyses. The absolute configuration was elucidated based on a combination of chemical degradations, chiral-phase HPLC analyses, spectroscopic analyses, and computational chemistry. Motobamide (1) moderately inhibited the growth of bloodstream forms of Trypanosoma brucei rhodesiense (IC50 2.3 μM). However, it exhibited a weaker cytotoxicity against normal human cells (IC50 55 μM).
Safe and Effective Method of Treating Ulcerative Colitis with Anti-IL12/IL23 Antibody
-
, (2020/04/10)
Described are methods and compositions for clinical proven safe and effective treatment of ulcerative colitis, particularly moderately to severely active ulcerative colitis in patients who have had an inadequate response to or are intolerant of a conventional or existing therapy by intravenous and/or subcutaneous administration of an anti-IL-12/IL-23p40 antibody.