85233-19-8

Basic information

• Product Name: BAPTA
• Synonyms: BAPTA;ETHYLENEDIOXYBIS(O-PHENYLENENITRILO)TETRAACETIC ACID;1,2-BIS-(O-AMINOPHENOXY)-ETHANE-N,N,N',N'-TETRAACETIC ACID;1,2-BIS(2-AMINOPHENOXY)ETHANE-N,N,N',N'-TETRAACETIC ACID;1,2-BIS(2-AMINOPHENOXY)ETHANE-N,N,N',N'- TETRAACETI;1,2-Bis-(2-Aminophenoxy) Ethane-N,N,N,-Tetra Acetic Acid;BAPTA (1,2-BIS(2-AMINOPHENOXY)ETHANE-N,N,N'',N'' -TETRAACETIC ACID);BAPTA, Ethylenedioxybis(o-phenylenenitrilo)tetraacetic acid, 2,2μ-(Ethylenedioxy)dianiline-N,N,Nμ,Nμ-tetraacetic acid
• CAS NO: 85233-19-8
• Molecular Formula: C₂₂H₂₄N₂O₁₀
• Molecular Weight: 476.43
• Product Categories: Chelating Agents & Ligands;Fluorescent Labels & Indicators;Amines;Aromatics;Aromatic
• Mol File: 85233-19-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 177-179 °C
• Boiling Point: 575.89°C (rough estimate)
• Flash Point: 417.4 °C
• Appearance: White to off-white/Powder
• Density: 1.4482 (rough estimate)
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in dimethyl sulfoxide
• PKA: 1.40±0.10(Predicted)
• Water Solubility: Soluble in water and sodium bicarbonate.
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• Merck: 14,957
• BRN: 5192406
• CAS DataBase Reference: BAPTA(CAS DataBase Reference)
• NIST Chemistry Reference: BAPTA(85233-19-8)
• EPA Substance Registry System: BAPTA(85233-19-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: MC0423000
• Hazardous Substances Data: 85233-19-8(Hazardous Substances Data)

Usage

Description

BAPTA free acid (85233-19-8) is a selective extracellular Ca2+ chelator. It is a widely used calcium sponge for chelating Ca2+?outside of intact cells.1 It’s a useful tool to probe the involvement of extracellular Ca2+ in cellular signaling.2,3 Non-cell-permeable.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 85233-19-8 differently. You can refer to the following data:
1. Highly selective calcium chelating reagent. Suitable for the spectrophotometric monitoring of Ca2+ levels.
2. BAPTA is a highly selective calcium chelating reagent. Lipophilic diesters of the chelating agent 1,2-Bis(2 aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA) are used for inhibition of proteolytic activities of certain metalloproteinases, calpain and TACE.
3. As calcium chelator; 19F labelled forms for measurement of intracellular calcium.

Definition

ChEBI: A polyamino carboxylic acid in which bis(carboxymethyl)nitrilo groups are bonded to C-2 and C-2' of 1,1'-[ethane-1,2-diylbis(oxy)]dibenzene.

General Description

In nature 1,2-Bis(2-Aminophenoxy)ethane-N,N,N′,N′-tetra acetic acid (BAPTA) is a main metabolic product of BAPTA -AM (BAPTA-tetra(actoxymethyl ester), a neuro protective agent in cerebral ischemia, in rats.BAPTA is an intercellular Ca2+ chelator.

Biological Activity

Selective calcium chelator.

References

1) Munoz et al. (2015), Different Stress-Induced Calcium Signatures Are Reported by Aequorin-Mediated Calcium Measurements in Living Cells of Aspergillus fumigatus; PLoS One, 10(9) e0138008 2) Wozniak et al. (2017), Extracellular Ca2+ is Required for Fertilization in the African Clawed Frog, Xenopus laevis; PLoS One, 12(1) e0170405 3) Didiasova et al. (2015), STIM1/ORAI1-mediated Ca2+ Influx Regulates Enolase-1 Exteriorization; J. Biol. Chem., 290 11983

Upstream product

• 88-75-5 2-hydroxynitrobenzene 
• 824-39-5 sodium o-nitrophenate 
• 52411-34-4 1,2-Bis(2-aminophenoxy)ethane 
• 51661-19-9 1,2-bis(2-nitrophenoxy)ethane 
• 73630-07-6 1,2-bis(2-aminophenoxy)ethane-N,N,N'N'-tetraacetic acid tetraethyl ester 

Downstream Products

• 123330-62-1 {(2-{2-[2-(Bis-carboxymethyl-amino)-phenoxy]-ethoxy}-phenyl)-[bis-(4,5-dimethoxy-2-nitro-phenyl)-methoxycarbonylmethyl]-amino}-acetic acid 
• 123330-64-3 {(2-{2-[2-(Bis-carboxymethyl-amino)-phenoxy]-ethoxy}-phenyl)-[hydroxy-(6-nitro-benzo[1,3]dioxol-5-yl)-methoxycarbonylmethyl]-amino}-acetic acid 
• 123330-65-4 [(2-{2-[2-(Bis-carboxymethyl-amino)-phenoxy]-ethoxy}-phenyl)-(3-nitro-quinolin-4-ylmethoxycarbonylmethyl)-amino]-acetic acid 
• 123330-63-2 [(2-{2-[2-(Bis-carboxymethyl-amino)-phenoxy]-ethoxy}-phenyl)-(4,5-dimethoxy-2-nitro-benzyloxycarbonylmethyl)-amino]-acetic acid 
• 123330-80-3 1,2-Bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid anhydride 

Relevant articles and documents

SYNTHESIS OF BAPTA-AM ANALOGUES CAPABLE OF ENHANCING THE VASCULAR PRODUCTION OF PROSTACYCLIN

About 30 analogues of BAPTA-AM, a potential antithrombotic agent, have been synthesized and tested for their effect on the production of prostacyclin.None of them was found to be a better enhancher of the production of prostacyclin by aortic endothelial cells than BAPTA-AM itself.The enhancing effect can be produced by compounds unable to chelate Ca2+, thus confirming that it is not related to their buffering capacity for free Ca2+.