(2S,3R)-2-amino-3-hydroxybutanoic acid

• ChemBase ID: 42
• Molecular Formular: C4H9NO3
• Molecular Mass: 119.11916
• Monoisotopic Mass: 119.05824315
• SMILES: O[C@@H]([C@H](N)C(=O)O)C
• Canonical SMILES: C[C@H]([C@@H](C(=O)O)N)O
• InChI: InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1
• InChIKey: AYFVYJQAPQTCCC-GBXIJSLDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-amino-3-hydroxybutanoic acid
• IUPAC Traditional name: L-threonine
• Synonyms: H-Thr-OH; (2S,3R)-2-Amino-3-hydroxybutyric acid; L-Threonine; 2-Amino-3-hydroxybutanoic acid; Threonine; (2S,3R)-2-amino-3-hydroxybutanoic acid; L-(-)-Threonine; 2-Amino-3-hydroxybutyric acid; (S)-Threonine; Threonine; [R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid; Threonin; L-Threonine; (2S,3R)-2-氨基-3-羟基丁酸; L-苏氨酸

Database IDs

• CAS Number: 80-68-2; 72-19-5
• EC Number: 200-774-1; 201-300-6
• MDL Number: MFCD00064270
• Beilstein Number: 1721646
• Merck Index: 149380
• PubChem SID: 24889191; 160963505; 24900544; 24900531; 24900195; 46506798
• PubChem CID: 6288
• CHEBI ID: 57926
• CHEMBL: 291747
• Chemspider ID: 6051
• DrugBank ID: DB00156
• Wikipedia Title: Threonine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.207432
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.4708102
• LogD (pH = 7.4): -3.4806278
• Log P: -3.4709635
• Molar Refractivity: 26.4598 cm^3
• Polarizability: 10.868561 Å^3
• Polar Surface Area: 83.55 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.01
• LOG S: 0.6
• Solubility (Water): 4.77e+02 g/l

PROPERTIES

Physical Property

• Solubility: (H2O, g/dl) 10.6(30°),14.1(52°),19.0(61°) in water; H2O: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, colorless; Soluble
• Apperance: powder
• Melting Point: 255°C dec.; 256 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -27.4°, c = 1 in H2O; [α]20/D -28.5±0.5°, c = 5% in H2O; -28 (c=5 in water)
• Hydrophobicity(logP): -3.5
• pKa: 2.63 (carboxyl), 10.43 (amino)

Safety Information

• Storage Warning: IRRITANT
• RTECS: XO8590000
• 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

Product Information

• Purity: ≥98% (TLC); ≥98.5%; ≥99.0% (NT); ≥99.5% (NT); 95+%; 98%; 98+%; 99.0-101.0%
• Grade: certified reference material; EP; JP; PharmaGrade; reagent grade; TraceCERT®; USP
• Optical Purity: ee: 99% (GLC)
• 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
• 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: ≤50 mg/kg; NH4+: ≤500 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, 20 °C (HV); ≤0.5% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• Product Line: BioXtra
• Linear Formula: CH3CH(OH)CH(NH2)CO2H

DETAILS

DrugBank - DB00156

• Drug Groups: approved; nutraceutical
• Description: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins. [PubChem]
• Indication: L-Threonine makes up collagen, elastin, and enamel protein. It aids proper fat metabolism in the liver, helps the digestive and intestinal tracts function more smoothly, and assists in metabolism and assimilation.
• Pharmacology: L-Threonine is an essential amino acid that helps to maintain the proper protein balance in the body. It is important for the formation of collagen, elastin, and tooth enamel, and aids liver and lipotropic function when combined with aspartic acid and methionine.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• External Links: Wikipedia

InterBioScreen - BB_SC-9459

2 Diastereomers

Sigma Aldrich - 89179

Other Notes
Preparation of threonine-sepharose, assay and purification of protein kinase C1; Amino acid spacing in isotachophoresis on polyacrylamide gel - a critical evaluation2,3; Growth requirement of various microorganisms4.

Sigma Aldrich - T4071

Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - T8441

Packaging
10 mg in autosample vial

Sigma Aldrich - 61506

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 - T8625

包装
1 kg in poly bottle
1, 10, 25, 100, 500 g in poly bottle
5 kg in poly drum