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(2S)-2-ammonio-4-(methylsulfanyl)butanoate

HCID 6992087
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
63-68-3
Standard SMILES
CSCC[C@H]([NH3+])C(=O)[O-]
InChIKey
FFEARJCKVFRZRR-BYPYZUCNSA-N
Molecular formula
C5H11NO2S
Average molar mass
149.21 g/mol
Monoisotopic mass
149.05104977

Overview

L-methionine zwitterion is zwitterionic form of L-methionine having a anionic carboxy group and a cationic amino group; major species at pH 7.3. It is a tautomer of a L-methionine.

Names & identifiers

Preferred name
(2S)-2-ammonio-4-(methylsulfanyl)butanoate
IUPAC
(2S)-2-azaniumyl-4-methylsulfanylbutanoate
English name
L-Methionine
Molecular formula
C5H11NO2S
Molecular weight
149.21

Names & synonyms

(2S)-2-ammonio-4-(methylsulfanyl)butanoate3tun4egaL-methionine zwitterion3f3d4eg44eg54eg64eg7CHEBI:57844(2S)-2-azaniumyl-4-(methylsulfanyl)butanoateMETHIONINE
Show more names
METH-MET-OHL-METL-Met-OHl-methioninMethioneH-L-MET-OHMethionine CRSL-Methionine, Animal-Free

Database identifiers

CAS
63-68-3
PubChem CID
6992087
ChEBI
CHEBI:57844

Properties

Computed structural properties

XLogP
-1.2
Topological polar surface area
93.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
9
Formal charge
0
Complexity
91.4

Experimental & physicochemical properties

LogP-1.87
Solubility56.6 mg/mL
Melting Point284 °C
Physical DescriptionSolid
Dissociation Constants2.28 (at 25 °C)

Physicochemical properties

Melting point
284 °C · 284 °C (dec.)(lit.)
alpha
23.25 · 23.25 º (c=2, 6N HCl)
Boiling point
393.91 °C · 393.91°C (estimate)
Density
1 · 1,34g/cm
bulk density
550 kg/m3 · 550kg/m3
refractive index
1.5216 · 1.5216 (estimate)
FLAVIS Number
17.027 · 17.027 | L-Methionine
storage temp.
20 · 20-25°C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

F
10-23
PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
tsca
TSCA listed
rtecs
PD0457000
hs_code
29304010
Toxicity
LD50 oral in rat: 36gm/kg
risk_code
33
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302
REACH Registrations
Active
Precautionary statements
P501-P270-P264-P301+P312+P330
Hazardous Substances Data
63-68-3(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

L-Methionine is a principle supplier of sulfur which prevents disorders of the hair, skin and nails; helps lower cholesterol levels by increasing the liver's production of lecithin; reduces liver fat and protects the kidneys; a natural chelating agent for heavy metals; regulates the formation of ammonia and creates ammonia-free urine which reduces bladder irritation; influences hair follicles and promotes hair growth. L-methionine may protect against the toxic effects of hepatotoxins, such as acetaminophen. Methionine may have antioxidant activity.

Mechanism of Action · 1 item

The mechanism of the possible anti-hepatotoxic activity of L-methionine is not entirely clear. It is thought that metabolism of high doses of acetaminophen in the liver lead to decreased levels of hepatic glutathione and increased oxidative stress. L-methionine is a precursor to L-cysteine. L-cysteine itself may have antioxidant activity. L-cysteine is also a precursor to the antioxidant glutathione. Antioxidant activity of L-methionine and metabolites of L-methionine appear to account for its possible anti-hepatotoxic activity. Recent research suggests that methionine itself has free-radical scavenging activity by virtue of its sulfur, as well as its chelating ability.

Metabolism/MetabolitesHepatic
Absorption, Distribution and ExcretionAbsorbed from the lumen of the small intestine into the enterocytes by an active transport process.
Tissue LocationsFibroblasts
Cellular LocationsExtracellular
Metabolite Pathways3-Phosphoglycerate dehydrogenase deficiency
Applications · 7 items

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
solubility
1 M · 1 M HCl: 0.5 M at 20 °C, clear, colorless
pka
2.13 · 2.13(at 25℃)
form
Solid
color
White
Odor
Slight characteristic
PH
5 · 5-7 (10g/l, H2O, 20℃)
biological source
synthetic
optical activity
20 · [α]20/D +23.7±0.5°, c = 5% in 5 M HCl
Water Solubility
Soluble
λmax
260 nm · λ: 260 nm Amax: 0.40λ: 280 nm Amax: 0.05
Merck
14 · 14,5975
BRN
1722294 · 1722294
Stability
Stable. Incompatible with strong oxidizing agents.
Major Application
peptide synthesispharmaceutical (small molecule)
InChI
1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
InChIKey
FFEARJCKVFRZRR-BYPYZUCNSA-N
SMILES
CSCC[C@H](N)C(O)=O
LogP
0.217 · 0.217 (est)
CAS DataBase Reference
63 · 63-68-3(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
L-METHIONINE
FDA 21 CFR
172.32 · 172.320; 310.545
EWG's Food Scores
1 · 1
FDA UNII
28 F7PNPL · AE28F7PNPL
ATC code
3 AB26 · V03AB26
NIST Chemistry Reference
L-Methionine(63-68-3)
EPA Substance Registry System
L-Methionine (63-68-3)
UNSPSC Code
41116107 · 41116107
NACRES
26 · NA.26
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
501 · P501-P270-P264-P301+P312+P330
PPE
95 · Eyeshields, Gloves, type N95 (US)
Risk Statements
33 · 33
Safety Statements
24 · 24/25
WGK Germany
2 · 2
RTECS
457000 · PD0457000
F
10 · 10-23
TSCA
TSCA listed
HS Code
29304010 · 29304010
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
63 · 63-68-3(Hazardous Substances Data)
Toxicity
50 oral · LD50 oral in rat: 36gm/kg
REACH Registrations
Active

DescriptionL-methionine is a sulfur-containing essential L-amino acid that is important in many body functions. Methionine is a dietary indispensable amino acid required for normal growth and development of humans, other mammals, and avian species. In addition to being a substrate for protein synthesis, it is an intermediate in transmethylation reactions, serving as the major methyl group donor.It must be obtained from diet and food sources since it is unable to be biosynthesized in the body. The minimum daily requirement of L-methionine for an adult male is 13 milligrams per kilogram of body weight. This quantity is normally easy to obtain from a complete diet. Methionine is accepted as the metabolic precursor for cysteine. Only the sulfur atom from methionine is transferred to cysteine; the carbon skeleton of cysteine is donated by serine. (PMID: 16702340).It helps the body produce SAMe (S-Adenosyl-L-methionine), which has been used to treat psychiatric illnesses, infertility, liver problems, premenstrual disorders, and musculoskeletal conditions. Studies on SAMe have shown that it is as effective as tricyclic antidepressants in alleviating depression. Ongoing studies that show promise are also being conducted to determine how effective L-Methionine may be for treating HIV/AIDS, liver damage, Parkinson's disease, and urinary tract infections.

UsesAmino acid drugs, nutritional supplements. Used for fatty liver and cirrhosis. Also widely used as feed additives to improve feed quality, improve the utilization of the native protein and promote animal growth. Such as DL-methionine can increase egg production of chickens, pigs make weight gain, more milk cows and so on. Adverse reaction: hepatic coma hanged. Nutritional supplements. One of the essential amino acids of the human body. Because the price is higher than DL-methionine and the results are equal, so commonly used DL-methionine. For biochemical studies and nutritional supplements, and as adjunctive treatment for pneumonia, liver cirrhosis and fatty liver.

DescriptionColorless or white lustrous plates, or a white crystalline powder. It has a slight, characteristic odor. It is soluble in water, in alkali solutions, and in dilute mineral acids. It is slightly soluble in alcohol and practically insoluble in ether.

UsesL-Methionine is used as an essential amino acid for human development and therapeutically acts as an antidote for acetaminophen poisoning. It serves as a chelating agent for heavy metals, as a flavoring agent and nutritional supplement for foods. It acts as a feed additive, vegetable oil enrichment and as a single cell protein. In addition to this, it is used as a hepatoprotectant and also acts as a lipotropic agent and prevents excess fat buildup in the liver.

Usesmethionine is slows down and normalizes oil gland sebum production. Methionine is also used as a texturizer in cosmetic creams. It is an essential amino acid found in a number of proteins and obtained by means of fermentation.

UsesEssential aminoacid for human development. Hepatoprotectant; antidote (acetominophen poisoning); urinary acidifier.

General DescriptionMinute hexagonal plates from dilute alcohol.

Preparation methods · 1 item

PreparationThe production method of choice for L-methionine is still the enzymatic resolution of racemic N-acetyl-methionine using acylase from Aspergillus oryzae. The production is carried out in a continuously operated fixed-bed or enzyme membrane reactor.

Upstream & downstream products

Upstream raw materials

AcroleinCopper (II) acetate monohydrateStorage tankMethyl mercaptanAcetyl DL-methionineAmmonium bicarbonatePotassium bisulfatePotassium sulfateSodium hydroxideAmmonium chlorideSodium cyanide(S)-2-[{(allyloxy)carbonyl}amino]-4-(methylthio)butanoic acid5'-deoxy-5'-fluoroadenosineBOC-L-Methioninemethyl methionateFMOC-L-MethionineL-Methionine sulfoxide

Downstream products

N-Acetyl-L-methionineH-Tyr-Gly-Gly-Phe-Met-OHDL-MethionineL-SelenomethionineL-LeucineD-Methionine

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
河北创之源生物科技有限公司13012111162 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
河北鸿韬生物工程有限公司15512737321 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
张家港市思普生化有限公司512-0512-58992291,58992287 18606280718 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
南京美博生物科技有限公司025-58619198 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
Abblis Chemicals LLC+1-832-373-8299 · [email protected]
大赛璐药物手性技术(上海)有限公司021-50460086-9 15921403865 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
台州市裕欣生物科技有限公司+86-0576--88902229 +86-13968687450 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
青岛保税区鲁联国际贸易有限公司0532-83893697 18561902820 · [email protected]
上海明褀化学有限公司86-21-60936353
上海思域化工科技有限公司86-21-34053660 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
北京伊诺凯科技有限公司400-810-7969 010-59572699 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
深圳康特腾科技有限公司86-0755-86635001 · [email protected]
Additional notes · 1 item

DefinitionChEBI: L-methionine is the L-enantiomer of methionine. It has a role as a nutraceutical, a micronutrient, an antidote to paracetamol poisoning, a human metabolite and a mouse metabolite. It is an aspartate family amino acid, a proteinogenic amino acid, a methionine and a L-alpha-amino acid. It is a conjugate base of a L-methioninium. It is a conjugate acid of a L-methioninate. It is an enantiomer of a D-methionine. It is a tautomer of a L-methionine zwitterion.