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63-68-3 molecular structure
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(2S)-2-amino-4-(methylsulfanyl)butanoic acid

ChemBase ID: 20
Molecular Formular: C5H11NO2S
Molecular Mass: 149.21134
Monoisotopic Mass: 149.0510496
SMILES and InChIs

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

Cite this record

CBID:20 http://www.chembase.cn/molecule-20.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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-2-Amino-4-(methylthio)butanoic acid
L-2-Amino-4-methyl<->thiobutanoic acid
L-METHIONINE, USP GRADE
L-Methionine
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
(S)-2-Amino-4-(methylmercapto)butyric acid
(S)-2-Amino-4-(methylthio)butyric acid
γ-Methylthio-α-aminobutyric Acid
(S)-2-Amino-4-(methylthio)butanoic acid
(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
L-蛋氨酸
CAS Number
63-68-3
EC Number
200-562-9
MDL Number
MFCD00063097
Beilstein Number
1722294
Merck Index
145975
PubChem SID
24897258
24883259
24896818
46505750
160963483
24897343
PubChem CID
6137

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.531921  H Acceptors
H Donor LogD (pH = 5.5) -2.1895034 
LogD (pH = 7.4) -2.1923122  Log P -2.1893265 
Molar Refractivity 37.586 cm3 Polarizability 15.069385 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -1.85  LOG S -0.8 
Solubility (Water) 2.39e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble0.5 M at 20 °C, clear, colorless expand Show data source
56.6 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
H2O: soluble25 mg/mL expand Show data source
H2O: soluble50 mg/mL expand Show data source
Water expand Show data source
Apperance
powder expand Show data source
White Solid expand Show data source
Melting Point
273-275°C (dec.) expand Show data source
284 °C (dec.)(lit.) expand Show data source
ca 280°C dec. expand Show data source
Optical Rotation
[α]20/D +23.7±0.5°, c = 5% in 5 M HCl expand Show data source
+23 (c=2 in 2N HCl) expand Show data source
Absorption Wavelength
λ: 260 nm Amax: 0.40 expand Show data source
λ: 280 nm Amax: 0.05 expand Show data source
Hydrophobicity(logP)
-1.9 expand Show data source
Storage Condition
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
PD0457000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
1 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
20-25°C expand Show data source
Gene Information
rat ... Ggt1(116568) expand Show data source
Purity
≥99% expand Show data source
≥98% (TLC) expand Show data source
≥98.5% expand Show data source
≥99% expand Show data source
≥99.0% (NT) expand Show data source
≥99.5% (NT) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98+% expand Show data source
99.0-101.0% expand Show data source
Grade
certified reference material expand Show data source
EP expand Show data source
JP expand Show data source
PharmaGrade expand Show data source
reagent grade expand Show data source
SAJ special grade expand Show data source
TraceCERT® expand Show data source
USP expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Suitability
meets EP, JP, USP testing specifications expand Show data source
suitable for cell culture expand Show data source
suitable for manufacturing use expand Show data source
Ignition Residue
≤0.1% expand Show data source
≤0.1% (as SO4) expand Show data source
Impurities
≤0.5% foreign amino acids expand Show data source
endotoxin, tested expand Show data source
insoluble matter, passes filter test expand Show data source
Cation Traces
Al: ≤5 mg/kg expand Show data source
As: ≤0.1 mg/kg expand Show data source
Ba: ≤5 mg/kg expand Show data source
Bi: ≤5 mg/kg expand Show data source
Ca: ≤10 mg/kg expand Show data source
Cd: ≤5 mg/kg expand Show data source
Co: ≤5 mg/kg expand Show data source
Cr: ≤5 mg/kg expand Show data source
Cu: ≤5 mg/kg expand Show data source
Fe: ≤5 mg/kg expand Show data source
K: ≤50 mg/kg expand Show data source
Li: ≤5 mg/kg expand Show data source
Mg: ≤5 mg/kg expand Show data source
Mn: ≤5 mg/kg expand Show data source
Mo: ≤5 mg/kg expand Show data source
Na: ≤100 mg/kg expand Show data source
Na: ≤50 mg/kg expand Show data source
NH4+: ≤100 mg/kg expand Show data source
Ni: ≤5 mg/kg expand Show data source
Pb: ≤5 mg/kg expand Show data source
Sr: ≤5 mg/kg expand Show data source
Zn: ≤5 mg/kg expand Show data source
Antion Traces
chloride (Cl-): ≤50 mg/kg expand Show data source
sulfate (SO42-): ≤100 mg/kg expand Show data source
sulfate (SO42-): ≤50 mg/kg expand Show data source
Biological Source
from non-animal source expand Show data source
Loss on Drying
≤0.1% loss on drying, 110 °C expand Show data source
≤0.1% loss on drying, 20 °C (HV) expand Show data source
Quality Level
GMP-COMPENDIA expand Show data source
λ
0.5 M in 1 M HCl expand Show data source
Product Line
BioUltra expand Show data source
Linear Formula
CH3SCH2CH2CH(NH2)CO2H expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC MP Biomedicals MP Biomedicals
DrugBank - DB00134 external link
Item Information
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 - M5308 external link
包装
10 mg in autosmp vl
Sigma Aldrich - M9625 external link
包装
1 kg in poly bottle
5, 25, 100, 500 g in poly bottle
Sigma Aldrich - M8439 external link
Packaging
Manufactured and Packaged under cGMP
Sigma Aldrich - 64319 external link
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 - 39496 external link
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
Toronto Research Chemicals - M260440 external link
Essential aminoacid for human development. Hepatoprotectant; antidote (acetominophen poisoning); urinary acidifier.
MP Biomedicals - 02194707 external link
Cell Culture Reagent
Crystalline
Purity: 99+%
MP Biomedicals - 02102291 external link
Crystalline
Purity: 99+%

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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