(2S)-2-amino-3-methylbutanoic acid

• ChemBase编号: 47
• 分子式: C5H11NO2
• 平均质量: 117.14634
• 单一同位素质量: 117.0789786
• SMILES: [C@H](C(C)C)(C(=O)O)N
• Canonical SMILES: N[C@H](C(=O)O)C(C)C
• InChI: InChI=1S/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m0/s1
• InChIKey: KZSNJWFQEVHDMF-BYPYZUCNSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-3-methylbutanoic acid
• IUPAC传统名: L-valine; valine
• 别名: (S)-α-氨基异戊酸; L-2-氨基-3-甲基丁酸; L-缬氨酸; L-2-Amino-3-methylbutanoic acid; L-α-Aminoisovaleric acid; (+)-2-Amino-3-methylbutyric Acid; (S)-α-Amino-β-methylbutyric Acid; L-(+)-α-Aminoisovaleric Acid; L-α-Amino-β-methylbutyric Acid; NSC 76038; L-2-Aminoisovaleric acid; (S)-(+)-2-Amino-3-methylbutyric acid; L-Valine; Valine; (S)-α-Aminoisovaleric acid; (2S)-2-Amino-3-methylbutanoic acid; (S)-Valine; (S)-a-Amino-b-methylbutyric acid; (S)-2-Amino-3-methylbutyric acid; (S)-2-Amino-3-methylbutanoic acid; 2-Amino-3-methylbutyric acid; 2-Amino-3-methylbutanoic acid; L-(+)-a-Aminoisovaleric acid; Valine; L-a-Amino-b-methylbutyric acid; L-Valine; (2R)-2-Amino-3-methylbutanoic acid; (R)-alpha-Aminoisovaleric acid; D-Valine

登记号

• CAS号: 640-68-6; 516-06-3; 72-18-4
• EC号: 208-220-0; 200-773-6
• MDL号: MFCD00064220; MFCD00064219
• Beilstein号: 1721136
• 默克索引号: 149909
• PubChem SID: 160963510; 24900696; 46504886; 24900695; 24900749; 24902117; 24890028
• PubChem CID: 1182; 6287
• CHEBI ID: 57762
• CHEMBL: 43068
• Chemspider ID: 6050
• DrugBank ID: DB00161
• KEGG ID: D00039
• 美国药典/FDA物质标识码: 4CA13A832H
• 维基百科标题: Valine
• Flavis Number: 17.028

理论计算性质

JChem

• Acid pKa: 2.7172735
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -1.9534721
• LogD (pH = 7.4): -1.9554411
• Log P: -1.9531364
• 摩尔折射率: 29.4929 cm^3
• 极化性: 12.004493 Å^3
• 极化表面积: 63.32 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.29
• LOG S: 0.26
• 溶解度: 2.14e+02 g/l

分子性质

理化性质

• 溶解度: 1 M HCl: soluble0.5 M at 20 °C, clear, colorless; H2O: soluble25 mg/mL; Soluble; soluble in water
• 外观: powder
• 熔点: >295(subl.)°C; 295-300 °C (subl.)(lit.); 298 °C decomp.; 315°C; ca 315°C
• 密度: 1.23; 1.23 g/ml; 1.316 g/cm^3
• 比旋光度: [α]20/D +26.7 to +29.0°, c = 8 in 6 M HCl; [α]20/D +27.0±0.5°, c = 5% in 5 M HCl; [α]20/D +27±1°, c = 5% in 5 M HCl; +27 (c=5 in 5N HCl)
• 紫外吸收波长: λ: 260 nm Amax: 0.15; λ: 280 nm Amax: 0.1
• 疏水性(logP): -2.2
• pKa: 2.32 (carboxyl), 9.62 (amino)

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: Irritant/Light Sensitive
• RTECS编号: YV9361000
• 德国WGK号: 1
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 20-25°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

产品相关信息

• 纯度: ≥98% (TLC); ≥98.5%; ≥99.0% (NT); ≥99.5% (NT); 11.8-12.1% N basis; 97%; 98%; 98.5-101.0%; 99%
• 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: ≤0.05%; ≤0.1% (as SO4)
• 杂质: ≤0.3% 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: ≤50 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: ≤200 mg/kg; NH4+: ≤150 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-): ≤50 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 110 °C
• 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: (CH3)2CHCH(NH2)CO2H

详细说明

MP Biomedicals - 02104760

Crystalline
Purity: 99%

MP Biomedicals - 02194769

Cell Culture Reagent
Crystalline
Purity: 99%

DrugBank - DB00161

• Drug Groups: approved; nutraceutical
• Description: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. [PubChem]
• Indication: Promotes mental vigor, muscle coordination, and calm emotions. May also be of use in a minority of patients with hepatic encephalopathy and in some with phenylketonuria.
• Pharmacology: L-valine is a branched-chain essential amino acid (BCAA) that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway. Valine is one of three branched-chain amino acids (the others are leucine and isoleucine) that enhance energy, increase endurance, and aid in muscle tissue recovery and repair. This group also lowers elevated blood sugar levels and increases growth hormone production. Supplemental valine should always be combined with isoleucine and leucine at a respective milligram ratio of 2:1:2. It is an essential amino acid found in proteins; important for optimal growth in infants and for growth in children and nitrogen balance in adults. The lack of L-valine may influence the growth of body, cause neuropathic obstacle, anaemia. It has wide applications in the field of pharmaceutical and food industry.
• Toxicity: Symptoms of hypoglycemia, increased mortality in ALS patients taking large doses of BCAAs.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorbed from the small intestine by a sodium-dependent active-transport process.
• External Links: PDRhealth

Sigma Aldrich - 94619

Other Notes
Protects enzymes against heat inactivation1; As spacer in isotachophoresis of serum proteins2,3; Growth requirement of various microorganisms4

Sigma Aldrich - V4638

包装
按照 cGMP 要求进行制造和包装

Sigma Aldrich - V0513

包装
10 mg in autosmp vl

Sigma Aldrich - W527718

包装
1 kg in poly bottle
1 sample in glass bottle
100 g in poly bottle

Sigma Aldrich - 50848

Analysis Note
此认证标准物质 (CRM) 的生产和认证都符合 ISO/IEC 17025 和 ISO Guide 34 的要求。此 CRM 可溯源到 NIST SRM。
General description
认证的含量经定量 NMR 确定，并且证书上标明不确定度和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - V0500

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

Toronto Research Chemicals - V094205

L-Valine is an essential amino acid and one of 20 proteinogenic amino acids. L-Valine cannot be manufactured by the body and must be acquired through diet or supplementation. L-valine is found in grains, dairy products, mushrooms, meats, peanuts and soy p

参考文献

• Choi, C.W. et al.: Anim. Feed Sci. Technol., 102, 15 (2002)
• Kolarski, D. et al.: Krmiva, 30, 155 (2002)
• Oba, M. et al.: J. Dairy Sci., 93, 2044 (2002)
• Mitrega, K. et al.: Pharmacol. Res., 64, 218 (2002)