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14871

Sigma-Aldrich

BICINE

BioUltra, ≥99.5% (T)

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Synonym(s):
N,N-Bis(2-hydroxyethyl)glycine
Empirical Formula (Hill Notation):
C6H13NO4
CAS Number:
150-25-4
Molecular Weight:
163.17
Beilstein:
1769362
EC Number:
205-755-1
MDL number:
MFCD00004295
UNSPSC Code:
12161700
PubChem Substance ID:
57647225

product line

BioUltra

Assay

≥99.5% (T)

form

powder or crystals

impurities

insoluble matter, passes filter test

ign. residue

≤0.1%

loss

≤0.1% loss on drying, 20 °C (HV)

pH

4.0-5.5 (25 °C, 1 M in H2O)

useful pH range

7.6-9.0

pKa (25 °C)

8.3

solubility

H2O: 1 M at 20 °C, clear, colorless

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤50 mg/kg

cation traces

Al: ≤5 mg/kg
As: ≤0.1 mg/kg
Ba: ≤5 mg/kg
Bi: ≤5 mg/kg
Ca: ≤20 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
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Sr: ≤5 mg/kg
Zn: ≤5 mg/kg

λ

1 M in H2O

UV absorption

λ: 260 nm Amax: 0.070
λ: 280 nm Amax: 0.040

SMILES string

OCCN(CCO)CC(O)=O

InChI

1S/C6H13NO4/c8-3-1-7(2-4-9)5-6(10)11/h8-9H,1-5H2,(H,10,11)

InChI key

FSVCELGFZIQNCK-UHFFFAOYSA-N

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Application

BICINE can be used to study biological buffers and zwitterionic compounds. N,N-Bis(2-hydroxyethyl)glycine has been used in a study that characterized refined crystal structures of human Ca2+/Zn2+-binding S100A3 protein. N,N-Bis(2-hydroxyethyl)glycine has also been used in a study to inform F1 antigen assembly.
Recommended buffer for low temperature biochemical work. Used in the preparation of stable substrate solution for serum guanase determination. Spacer in plasma protein fractionation with Sephadex® by isotachophoresis.

Legal Information

Sephadex is a registered trademark of Cytiva

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Masaki Unno et al.
Journal of molecular biology, 408(3), 477-490 (2011-03-08)
S100A3, a member of the EF-hand-type Ca(2+)-binding S100 protein family, is unique in its exceptionally high cysteine content and Zn(2+) affinity. We produced human S100A3 protein and its mutants in insect cells using a baculovirus expression system. The purified wild-type
E Gopinath et al.
Proceedings of the National Academy of Sciences of the United States of America, 86(9), 3041-3044 (1989-05-01)
The nature and rate of reduction of Hg2+ to Hg0 by 1,5-dihydro-3,(3-sulfopropyl)lumiflavin (FIH2) in buffered aqueous solutions (pH 4.7) is dependent on the ligation of Hg2+. In the presence of N,N-bis(2-hydroxyethyl)glycine or when ligated to ethylenediaminetetraacetic acid, the reduction is
The myosin dimer: an intermediate in the self-assembly of the thick filament of vertebrate skeletal muscle.
J S Davis et al.
FEBS letters, 140(2), 293-297 (1982-04-19)
R Nakon et al.
Science (New York, N.Y.), 221(4612), 749-750 (1983-08-19)
Metal-ion affinity (formation) constants were determined for two "Good's" buffers, N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid (TES) and N,N-bis(2-hydroxyethyl)glycine (bicine). The metal chelates formed undergo loss of an internal ligand (alcohol) proton (bicine) and undergo hydrolysis (bicine and TES) and dimerization reactions (TES). Bicine
Raewyn M Town et al.
The journal of physical chemistry. A, 112(12), 2563-2571 (2008-03-04)
The impact of ligand protonation on the complexation kinetics of higher-order complexes is quantitatively described. The theory is formulated on the basis of the usual situation for metal complex formation in aqueous systems in which the exchange of water for
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