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

• ChemBase编号: 20
• 分子式: C5H11NO2S
• 平均质量: 149.21134
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-4-(methylsulfanyl)butanoic acid
• IUPAC传统名: L-methionine
• 商标名: Acimethin; Cymethion
• 别名: 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; (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

登记号

• CAS号: 63-68-3
• EC号: 200-562-9
• MDL号: MFCD00063097
• Beilstein号: 1722294
• 默克索引号: 145975
• PubChem SID: 160963483; 24897258; 24897343; 46505750; 24883259; 24896818
• PubChem CID: 6137

理论计算性质

JChem

• Acid pKa: 2.531921
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -2.1895034
• LogD (pH = 7.4): -2.1923122
• Log P: -2.1893265
• 摩尔折射率: 37.586 cm^3
• 极化性: 15.069385 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.85
• LOG S: -0.8
• 溶解度: 2.39e+01 g/l

分子性质

理化性质

• 溶解度: 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
• 外观: powder; White Solid
• 熔点: 273-275°C (dec.); 284 °C (dec.)(lit.); ca 280°C dec.
• 比旋光度: [α]20/D +23.7±0.5°, c = 5% in 5 M HCl; +23 (c=2 in 2N HCl)
• 紫外吸收波长: λ: 260 nm Amax: 0.40; λ: 280 nm Amax: 0.05
• 疏水性(logP): -1.9

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: PD0457000
• 德国WGK号: 1
• TSCA收录: false; 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 20-25°C

药理学性质

• 相关基因信息: rat ... Ggt1(116568)

产品相关信息

• 纯度: ≥99%; ≥98% (TLC); ≥98.5%; ≥99%; ≥99.0% (NT); ≥99.5% (NT); 95+%; 97%; 98%; 98+%; 99.0-101.0%
• 级别: certified reference material; EP; JP; PharmaGrade; reagent grade; SAJ special grade; TraceCERT®; USP
• 适用性: meets EP, JP, USP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.1%; ≤0.1% (as SO4)
• 杂质: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• 痕量阳离子: 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
• 痕量阴离子: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤100 mg/kg; sulfate (SO42-): ≤50 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.1% loss on drying, 110 °C; ≤0.1% loss on drying, 20 °C (HV)
• 产品质量级别: GMP-COMPENDIA
• λ: 0.5 M in 1 M HCl
• 产品线: BioUltra
• 线性分子式: CH3SCH2CH2CH(NH2)CO2H

详细说明

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

包装
按照 cGMP 制造和包装

Sigma Aldrich - 39496

Analysis Note
该有证标准物质 (CRM) 根据 ISO/IEC 17025 和 ISO 指南 34 生产和认证。该有证标准物质可溯源到 NIST 标准参考物质。
General description
证书上给出了含不确定度的认证含量（定量 NMR 法测定）和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 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.

参考文献

• 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)