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A4926

1,2-Bis(2-Aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid

Name: 1,2-Bis(2-Aminophenoxy)ethane-<I>N,N,N′,N′</I>-tetraacetic acid
Brand: ALDRICH

98%

Synonym(s):

2,2′-(Ethylenedioxy)dianiline-N,N,N′,N′-tetraacetic acid, BAPTA, Ethylenedioxybis(o-phenylenenitrilo)tetraacetic acid

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₄N₂O₁₀

CAS Number:

85233-19-8

Molecular Weight:

476.43

UNSPSC Code:

12352103

NACRES:

NA.23

PubChem Substance ID:

57653856

MDL number:

MFCD00036255

Beilstein/REAXYS Number:

5192406

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Properties

Quality Level

200

assay

98%

form

powder

density

±1.494 g/cm³ at 25 °C (Predicted)

storage temp.

2-8°C

SMILES string

OC(=O)CN(CC(O)=O)c1ccccc1OCCOc2ccccc2N(CC(O)=O)CC(O)=O

InChI

1S/C22H24N2O10/c25-19(26)11-23(12-20(27)28)15-5-1-3-7-17(15)33-9-10-34-18-8-4-2-6-16(18)24(13-21(29)30)14-22(31)32/h1-8H,9-14H2,(H,25,26)(H,27,28)(H,29,30)(H,31,32)

InChI key

FTEDXVNDVHYDQW-UHFFFAOYSA-N

Description

General description

1,2-Bis(2-Aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid (BAPTA) is a high-affinity, fast-acting calcium chelator for precise intracellular Ca²⁺ regulation. Its rapid binding kinetics and strong selectivity for Ca²⁺ make it essential for investigating calcium-dependent processes in neuronal and cellular research. BAPTA and its membrane-permeable derivative, BAPTA-AM, allow controlled manipulation of Ca²⁺dynamics, facilitating studies on calcium signaling, neuroprotection, and cell signaling pathways.

Application

The product can be used in various R&D applications such as:

Neuroscience: Used to suppress intracellular Ca²⁺ overload, reduce neuronal apoptosis, and preserve electrophysiological function in injury models, demonstrating strong neuroprotective action.

Pharmacology: Enables precise buffering of intracellular Ca²⁺ levels, allowing researchers to distinguish Ca²⁺‑ dependent drug effects and dissect therapeutic signaling mechanisms.

Other Notes

pKa: 1.401 ± 0.10 (predicted)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Determination of 1,2-bis (2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA free acid) in rat plasma, urine and feces by liquid chromatography with UV and tandem mass spectrometric detection.

Zheng Feng et al.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 878(30), 3052-3058 (2010-10-23)

BAPTA free acid was identified as the main metabolic product of 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid tetra(actoxymethyl ester) (BAPTA-AM), a neuroprotective agent in cerebral ischemia, in rats. In this paper, liquid chromatography-ultraviolet (LC-UV) and mass spectrometry/mass spectrometry (LC-MS/MS) methods were employed for the

Inhibition of phospholipase C activity in Drosophila photoreceptors by 1,2-bis(2-aminophenoxy)ethane N,N,N',N'-tetraacetic acid (BAPTA) and di-bromo BAPTA.

Roger C Hardie

Cell calcium, 38(6), 547-556 (2005-09-06)

In vivo light-induced and basal hydrolysis of phosphatidyl inositol 4,5-bisphosphate (PIP2) by phospholipase C (PLC) were monitored in Drosophila photoreceptors using genetically targeted PIP2-sensitive ion channels (Kir2.1) as electrophysiological biosensors for PIP2. In cells loaded via patch pipettes with varying

1,2-bis(2-Aminophenoxy)ethane-N,N,N',N'-tetraacetic acid induces caspase-mediated apoptosis and reactive oxygen species-mediated necrosis in cultured cortical neurons.

K S Han et al.

Journal of neurochemistry, 78(2), 230-239 (2001-07-20)

Sustained alteration in [Ca(2+)]i triggers neuronal death. We examined morphological and signaling events of Ca(2+)-deficiency-induced neuronal death. Cortical cell cultures exposed to 20 microM 1,2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA-AM), an intracellular calcium chelator, underwent neuronal apoptosis within 12 h that was evident

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