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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Velasco-Bejarano, B.; et al.
Synlett, 921-921 (2007)
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%
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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