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

• ChemBase ID: 47
• Molecular Formular: C5H11NO2
• Molecular Mass: 117.14634
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-methylbutanoic acid
• IUPAC Traditional name: L-valine; valine
• Synonyms: 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; (S)-α-氨基异戊酸; L-2-氨基-3-甲基丁酸; L-缬氨酸

Database IDs

• CAS Number: 640-68-6; 516-06-3; 72-18-4
• EC Number: 208-220-0; 200-773-6
• MDL Number: MFCD00064220; MFCD00064219
• Beilstein Number: 1721136
• Merck Index: 149909
• PubChem SID: 160963510; 24900749; 24900696; 24890028; 46504886; 24900695; 24902117
• PubChem CID: 1182; 6287
• CHEBI ID: 57762
• CHEMBL: 43068
• Chemspider ID: 6050
• DrugBank ID: DB00161
• KEGG ID: D00039
• Unique Ingredient Identifier: 4CA13A832H
• Wikipedia Title: Valine
• Flavis Number: 17.028

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.7172735
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.9534721
• LogD (pH = 7.4): -1.9554411
• Log P: -1.9531364
• Molar Refractivity: 29.4929 cm^3
• Polarizability: 12.004493 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.29
• LOG S: 0.26
• Solubility (Water): 2.14e+02 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble0.5 M at 20 °C, clear, colorless; H2O: soluble25 mg/mL; Soluble; soluble in water
• Apperance: powder
• Melting Point: >295(subl.)°C; 295-300 °C (subl.)(lit.); 298 °C decomp.; 315°C; ca 315°C
• Density: 1.23; 1.23 g/ml; 1.316 g/cm^3
• Optical Rotation: [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)
• Absorption Wavelength: λ: 260 nm Amax: 0.15; λ: 280 nm Amax: 0.1
• Hydrophobicity(logP): -2.2
• pKa: 2.32 (carboxyl), 9.62 (amino)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Irritant/Light Sensitive
• RTECS: YV9361000
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 20-25°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320)

Product Information

• Purity: ≥98% (TLC); ≥98.5%; ≥99.0% (NT); ≥99.5% (NT); 11.8-12.1% N basis; 97%; 98%; 98.5-101.0%; 99%
• 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: ≤0.05%; ≤0.1% (as SO4)
• Impurities: ≤0.3% 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: ≤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
• Antion Traces: chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• λ: 0.5 M in 1 M HCl
• Product Line: BioUltra
• Linear Formula: (CH3)2CHCH(NH2)CO2H

DETAILS

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

Packaging
Manufactured and packaged under cGMP

Sigma Aldrich - V0513

包装
10 mg in autosmp vl

Sigma Aldrich - W527718

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

Sigma Aldrich - 50848

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 - 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

REFERENCES

• 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)