(2S)-2-amino-4-(methylsulfanyl)butanoic acid

• ChemBase ID: 20
• Molecular Formular: C5H11NO2S
• Molecular Mass: 149.21134
• Monoisotopic Mass: 149.0510496
• SMILES: S(CC[C@H](N)C(=O)O)C
• Canonical SMILES: CSCC[C@@H](C(=O)O)N
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(methylsulfanyl)butanoic acid
• IUPAC Traditional name: L-methionine
• Brand Name: Acimethin; Cymethion
• Synonyms: (S)-2-Amino-4-(methylthio)butanoic acid; L-2-Amino-4-(methylthio)butanoic acid; (S)-2-Amino-4-(methylthio)butyric acid; Cymethion; S-Methyl-L-momocysteine; L-α-Amino-γ-methylthiobutyric Acid; NSC 22946; S-Methionine; S-Methyl-L-homocysteine; h-Met-oh; l-Methionine; α-Amino-γ-methylmercaptobutyric Acid; γ-Methylthio-α-aminobutyric Acid; (S)-2-Amino-4-(methylmercapto)butyric acid; L-Methionine; L-METHIONINE, USP GRADE; L-2-Amino-4-methyl<->thiobutanoic acid; (S)-2-Amino-4-(methylthio)butanoic acid; 2-Amino-4-(methylthio)butyric acid; a-Amino-g-methylmercaptobutyric acid; g-Methylthio-a-aminobutyric acid; L-(-)-Methionine; L-a-Amino-g-methylthiobutyric acid; Methionine; L-Methionine; L-蛋氨酸; (S)-2-氨基-4-(甲硫基)丁酸; L-2-氨基-4-(甲硫基)丁酸; L-甲硫氨酸

Database IDs

• CAS Number: 63-68-3
• EC Number: 200-562-9
• MDL Number: MFCD00063097
• Beilstein Number: 1722294
• Merck Index: 145975
• PubChem SID: 24883259; 24896818; 24897258; 24897343; 46505750; 160963483
• PubChem CID: 6137

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.531921
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.1895034
• LogD (pH = 7.4): -2.1923122
• Log P: -2.1893265
• Molar Refractivity: 37.586 cm^3
• Polarizability: 15.069385 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.85
• LOG S: -0.8
• Solubility (Water): 2.39e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble0.5 M at 20 °C, clear, colorless; 56.6 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; H2O: soluble25 mg/mL; H2O: soluble50 mg/mL; Water
• Apperance: powder; White Solid
• Melting Point: 273-275°C (dec.); 284 °C (dec.)(lit.); ca 280°C dec.
• Optical Rotation: [α]20/D +23.7±0.5°, c = 5% in 5 M HCl; +23 (c=2 in 2N HCl)
• Absorption Wavelength: λ: 260 nm Amax: 0.40; λ: 280 nm Amax: 0.05
• Hydrophobicity(logP): -1.9

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: PD0457000
• German water hazard class: 1
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 20-25°C

Pharmacology Properties

• Gene Information: rat ... Ggt1(116568)

Product Information

• Purity: ≥99%; ≥98% (TLC); ≥98.5%; ≥99%; ≥99.0% (NT); ≥99.5% (NT); 95+%; 97%; 98%; 98+%; 99.0-101.0%
• Grade: certified reference material; EP; JP; PharmaGrade; reagent grade; SAJ special grade; TraceCERT®; USP
• Suitability: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.1%; ≤0.1% (as SO4)
• Impurities: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤100 mg/kg; Na: ≤50 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.1% loss on drying, 110 °C; ≤0.1% loss on drying, 20 °C (HV)
• Quality Level: GMP-COMPENDIA
• λ: 0.5 M in 1 M HCl
• Product Line: BioUltra
• Linear Formula: CH3SCH2CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02102291

Crystalline
Purity: 99+%

MP Biomedicals - 02194707

Cell Culture Reagent
Crystalline
Purity: 99+%

DrugBank - DB00134

• Drug Groups: approved; nutraceutical
• Description: A sulfur containing essential amino acid that is important in many body functions. It is a chelating agent for heavy metals. [PubChem]
• Indication: Used for protein synthesis including the formation of SAMe, L-homocysteine, L-cysteine, taurine, and sulfate.
• Pharmacology: 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.
• Toxicity: Doses of L-methionine of up to 250 mg daily are generally well tolerated. Higher doses may cause nausea, vomiting and headache. Healthy adults taking 8 grams of L-methionine daily for four days were found to have reduced serum folate levels and leucocytosis. Healthy adults taking 13.9 grams of L-methionine daily for five days were found to have changes in serum pH and potassium and increased urinary calcium excretion. Schizophrenic patients given 10 to 20 grams of L-methionine daily for two weeks developed functional psychoses. Single doses of 8 grams precipitated encephalopathy in patients with cirrhosis.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorbed from the lumen of the small intestine into the enterocytes by an active transport process.
• External Links: PDRhealth

Sigma Aldrich - 64319

Other Notes
Synthesis of labels for protonation studies by Fourier Transform Infrared Methods for L-glutaric-513C acid1; Spacer in isotachophoresis of serum proteins2; Essential in culture media for some malignant human cell lines3,4; Growth requirement of various microorganisms5

Sigma Aldrich - M5308

包装
10 mg in autosmp vl

Sigma Aldrich - M8439

Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - 39496

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - M9625

包装
1 kg in poly bottle
5, 25, 100, 500 g in poly bottle

Toronto Research Chemicals - M260440

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

REFERENCES

• Benevenga, N.J., et al.: J. Agric. Food Chem., 22, 2 (1974)
• Fleisher, L.D., et al.: Clin. Endocrinol. Metab., 3, 37 (1974)
• Meinnel, T., et al.: Biochimie, 75, 1061 (1974)