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D9754

Sigma-Aldrich

2-Aminoethyl diphenylborinate

97%

Synonym(s):

2-APB, 2-Aminoethoxydiphenyl borate, 2-Aminoethyl diphenyl borate, Diphenylboric acid 2-aminoethyl ester, Diphenylborinic acid, NSC 17107

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About This Item

Linear Formula:
(C6H5)2BOCH2CH2NH2
CAS Number:
524-95-8
Molecular Weight:
225.09
Beilstein:
2942273
EC Number:
208-366-5
MDL number:
MFCD00014823
UNSPSC Code:
12352103
PubChem Substance ID:
57654145
NACRES:
NA.22

Quality Level

200

Assay

97%

form

powder

storage temp.

−20°C

SMILES string

NCCOB(c1ccccc1)c2ccccc2

InChI

1S/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2

InChI key

BLZVCIGGICSWIG-UHFFFAOYSA-N

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Application

Reactant for:
  • Preparation of apoptotic inducers

  • Activator of the Orai3 (ORAI calcium release-activated calcium modulator 3) protein
  • Inhibits Ca2+ influx through transient receptor potential 2 channels in rat dorsal root ganglion neurons
  • Membrane-permeable SOCE (store operated calcuym entry) inhibitor

Biochem/physiol Actions

Membrane-permeable modulator of intracellular IP3-induced calcium release.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3896
BCCM4346
BCCM1318
BCCK4375
BCCH1285

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Akinobu Z Suzuki et al.
Bioorganic & medicinal chemistry letters, 20(4), 1395-1398 (2010-01-26)
Store-operated calcium entry (SOCE) is an important mechanism for replenishing intracellular calcium stores and for sustaining calcium signaling. We developed a method for synthesis of bisboron compounds that have two borinic acids or their esters in one molecule. These compounds
Mustafa Nazıroğlu et al.
The Journal of membrane biology, 241(2), 69-75 (2011-04-22)
Exposure to oxidative stress causes health problems, including sensory neuron neuropathy and pain. Rotenone is a toxin used to generate intracellular oxidative stress in neurons. However, the mechanism of toxicity in dorsal root ganglion (DRG) neurons has not been characterized.
T Maruyama et al.
Journal of biochemistry, 122(3), 498-505 (1997-11-05)
The effects of a novel membrane-penetrable modulator, 2APB (2-aminoethoxy diphenyl borate), on Ins(1,4,5)P3-induced Ca2+ release were examined. 2APB inhibited Ins(1,4,5)P3-induced Ca2+ release from rat cerebellar microsomal preparations without affecting [3H]Ins(1,4,5)P3 binding to its receptor. The IC50 value (concentration producing 50%
Velasco-Bejarano, B.; et al.
Synlett, 921-921 (2007)
Judith Bergsmann et al.
The Journal of biological chemistry, 286(36), 31565-31575 (2011-07-05)
STIM1 and Orai represent the key components of Ca(2+) release-activated Ca(2+) channels. Activation of Orai channels requires coupling of the C terminus of STIM1 to the N and C termini of Orai. Although the latter appears to be central in
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