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, also known as 1,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid, is a selective extracellular Ca2+ chelator. It is a widely used calcium sponge for chelating Ca2+ outside of intact cells and serves as a useful tool to probe the involvement of extracellular Ca2+ in cellular signaling. BAPTA is non-cell-permeable and has a variety of applications in different industries.

Uses

Used in Spectrophotometric Monitoring:
BAPTA is used as a highly selective calcium chelating reagent for the spectrophotometric monitoring of Ca2+ levels. This application allows for the accurate measurement and analysis of calcium ions in various solutions.
Used in Inhibition of Proteolytic Activities:
In the pharmaceutical industry, lipophilic diesters of BAPTA are used for the inhibition of proteolytic activities of certain metalloproteinases, calpain, and TACE. This helps in studying and controlling the activity of these enzymes in various biological processes.
Used in Calcium Chelation:
BAPTA is used as a calcium chelator in various applications, including the measurement of intracellular calcium using 19F labeled forms. This allows researchers to monitor and analyze the levels of calcium ions within cells, which is crucial for understanding various cellular processes and functions.

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 
• 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 
• 824-39-5 sodium o-nitrophenate 
• 52411-34-4 1,2-Bis(2-aminophenoxy)ethane 

Downstream Products

• 123330-80-3 1,2-Bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid anhydride 
• 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 

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+.