(acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[2-(2-{2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy}ethoxy)phenyl]amino)acetate

• ChemBase ID: 81071
• Molecular Formular: C34H40N2O18
• Molecular Mass: 764.684
• Monoisotopic Mass: 764.22761245
• SMILES: N(c1c(cccc1)OCCOc1c(cccc1)N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• Canonical SMILES: O=C(CN(c1ccccc1OCCOc1ccccc1N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)OCOC(=O)C
• InChI: InChI=1S/C34H40N2O18/c1-23(37)47-19-51-31(41)15-35(16-32(42)52-20-48-24(2)38)27-9-5-7-11-29(27)45-13-14-46-30-12-8-6-10-28(30)36(17-33(43)53-21-49-25(3)39)18-34(44)54-22-50-26(4)40/h5-12H,13-22H2,1-4H3
• InChIKey: YJIYWYAMZFVECX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[2-(2-{2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy}ethoxy)phenyl]amino)acetate
• IUPAC Traditional name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[2-(2-{2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]phenoxy}ethoxy)phenyl]amino)acetate
• Synonyms: 1,2-Bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid tetrakis(acetoxymethyl ester); BAPTA-AM; N,N'-[1,2-Ethanediylbis(oxy-2,1-phenylene)]bis[N-[2-[(acetyloxy)methoxy]-2-oxoethyl]glycine 1,1'-Bis[(acetyloxy)methyl] Ester; 1,2-Bis(2-aminophenoxy)ethane-N,N,N’,N’-tetraacetic Acid Tetraacetoxymethyl Ester; BAPTA-AM; BAPTA-AM; 1,2-Bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid, tetraacetoxymethyl ester; 1,2-bis(o-AMINOPHENOXY)ETHANE-N,N,N',N'-TETRAACETIC ACID TETRAACETOXYMETHYL ESTER

Database IDs

• CAS Number: 126150-97-8
• MDL Number: MFCD00036696
• Beilstein Number: 7458534
• PubChem SID: 162068190; 24890502; 24847309
• PubChem CID: 2293

CALCULATED PROPERTIES

• H Acceptors: 12
• H Donor: 0
• LogD (pH = 5.5): 1.6157187
• LogD (pH = 7.4): 1.6157187
• Log P: 1.6157187
• Molar Refractivity: 176.3586 cm^3
• Polarizability: 70.69166 Å^3
• Polar Surface Area: 235.34 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 94-96°C

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Irritant/Store at -20°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: >90%; ≥95% (HPLC); ≥98.0% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C34H40N2O18

DETAILS

MP Biomedicals - 02195709

Purity: >90%
A cell permeable derivative of BAPTA widely used as an intracellular calcium sponge.

Apollo Scientific Ltd - OR2370T

A cell permeable derivative of BAPTA.

Sigma Aldrich - A1076

Frequently Asked Questions
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Biochem/physiol Actions
Selective chelator of intracellular Ca2+ stores.
Linkage
Membrane-permeable form of BAPTA.

Sigma Aldrich - 11696

Other Notes
Membrane-permeable form of BAPTA. Can be loaded into cells where it is hydrolysed by cytosolic esterases and trapped as the active chelator1

Toronto Research Chemicals - B123700

BAPTA-AM is a lipophilic diester of BAPTA used for inhibition of proteolytic activities of certain metalloproteinases, calpain and TACE. Fluorescence: max. Abs. 287nm; e x 10-3: 5.9

REFERENCES

• Li, B., et al.: Brain Res., 1226, 199 (2008)
• Chen, W., et al.: Mol. Endocrinol., 22, 1754 (2008)
• Tonkikh, A., et al.: Neurosci., 159, 1300 (2008)