2-[(carbamoylmethyl)(carboxymethyl)amino]acetic acid

• ChemBase ID: 2523
• Molecular Formular: C6H10N2O5
• Molecular Mass: 190.154
• Monoisotopic Mass: 190.05897143
• SMILES: NC(=O)CN(CC(=O)O)CC(=O)O
• Canonical SMILES: NC(=O)CN(CC(=O)O)CC(=O)O
• InChI: InChI=1S/C6H10N2O5/c7-4(9)1-8(2-5(10)11)3-6(12)13/h1-3H2,(H2,7,9)(H,10,11)(H,12,13)
• InChIKey: QZTKDVCDBIDYMD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(carbamoylmethyl)(carboxymethyl)amino]acetic acid
• IUPAC Traditional name: [(carbamoylmethyl)(carboxymethyl)amino]acetic acid
• Synonyms: 2,2'-[(2-Amino-2-oxoethyl)imino]diacetic acid; ADA; N-(2-Acetamido)iminodiacetic acid; N-(Carbamoylmethyl)iminodiacetic acid; N-(2-ACETAMIDO)-2-IMINODIACETIC ACID; N-(2-Acetamido)Iminodiacetic Acid; ADA; N-(2-乙酰氨基)-亚氨基二乙酸; N-(氨基甲酰甲基)亚氨基二乙酸; 乙酰氨基亚胺乙酸; N-(2-乙酰氨基)亚氨基二乙酸

Database IDs

• CAS Number: 26239-55-4
• EC Number: 247-530-0
• MDL Number: MFCD00008031
• Beilstein Number: 1787181
• Merck Index: 14147
• PubChem SID: 24845005; 24891404; 24891315; 24845006; 46505907; 160965973
• PubChem CID: 117765

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.308566
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -6.135132
• LogD (pH = 7.4): -8.659291
• Log P: -3.8947408
• Molar Refractivity: 40.0641 cm^3
• Polarizability: 15.854732 Å^3
• Polar Surface Area: 120.93 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.6
• LOG S: -0.59
• Solubility (Water): 4.91e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M NaOH: soluble0.05 M, clear, colorless; H2O: soluble0.05 M at 20 °C, clear, colorless; H2O: soluble0.05 M, clear, colorless
• Melting Point: ~200 °C (dec.); 219 °C (dec.)(lit.); 219°C; ca 218°C dec.
• Absorption Wavelength: λ: 260 nm Amax: 0.20; λ: 280 nm Amax: 0.05
• pKa: 6.6 (20°C); 6.6 (25°C)
• pH: 1.5-3.0 (25 °C, 0.01 M in H2O)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (titration); ≥98.0% (T); ≥99.0% (T); 98+%
• Ignition Residue: ≤0.1%; ≤0.5%
• Impurities: ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter; insoluble matter, passes filter test
• Cation Traces: Al: ≤0.0005%; Al: ≤5 mg/kg; As: ≤0.1 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: ≤0.0005%; Fe: ≤10 mg/kg; Fe: ≤5 mg/kg; K: ≤0.005%; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤2000 mg/kg; Na: ≤500 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤0.05%; chloride (Cl-): ≤1000 mg/kg; chloride (Cl-): ≤2000 mg/kg; sulfate (SO42-): ≤0.05%; sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤0.5% loss on drying, 20 °C (HV)
• Quality Level: ELITE
• λ: 0.05 M in H2O
• Useful pH Range: 6.0 - 7.2
• Product Line: BioUltra; BioXtra
• Linear Formula: H2NCOCH2N(CH2CO2H)2

DETAILS

MP Biomedicals - 02150223

Free Acid
Biological buffer:
pKa=6.6 at 25°C; pH range 6.0-7.2

DrugBank - DB02810

Drug information: experimental

Sigma Aldrich - A8074

Application
Biological buffer component with sodium hydroxide and sodium chloride (pH 5.67-7.57, useful pH range 6.4-7.4).1 Used to prepare immobilized pH gradients.2

Sigma Aldrich - A9883

Application
Biological buffer component with sodium hydroxide and sodium chloride (pH 5.67-7.57, useful pH range 6.4-7.4).1 Used to prepare immobilized pH gradients.2

Sigma Aldrich - 00307

Application
Biological buffer component with sodium hydroxide and sodium chloride (pH 5.67-7.57, useful pH range 6.4-7.4).1 Used to prepare immobilized pH gradients.2
ADA, or N-(2-Acetamido)iminodiacetic acid, can be used to study biological buffers and zwitterionic compounds. ADA has been used in a study to describe the application of scanning capacitively coupled contactless conductivity detection (SC(4)D) for the determination of pH dependant behaviour of two aminopolycarboxylates immobilised onto the surface of a monolithic capillary column.

Sigma Aldrich - 00308

Application
Biological buffer component with sodium hydroxide and sodium chloride (pH 5.67-7.57, useful pH range 6.4-7.4).1 Used to prepare immobilized pH gradients.2

REFERENCES

• Biological buffer, pK_a = 6.9 at 20^o: Biochemistry, 5, 467 (1966).