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A8486

Sigma-Aldrich

N-(p-Amylcinnamoyl)anthranilic acid

≥98% (HPLC)

Synonym(s):

2-[[1-oxo-3-(4-Pentylphenyl)-2-propen-1-yl]amino]-benzoic acid, ACA, N-(4-Pentylcinnamoyl)anthranilic acid

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About This Item

Empirical Formula (Hill Notation):
C21H23NO3
CAS Number:
99196-74-4
Molecular Weight:
337.41
MDL number:
MFCD00211365
UNSPSC Code:
12352106
PubChem Substance ID:
329770958
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

SMILES string

CCCCCc1ccc(\C=C\C(=O)Nc2ccccc2C(O)=O)cc1

InChI

1S/C21H23NO3/c1-2-3-4-7-16-10-12-17(13-11-16)14-15-20(23)22-19-9-6-5-8-18(19)21(24)25/h5-6,8-15H,2-4,7H2,1H3,(H,22,23)(H,24,25)/b15-14+

InChI key

GAMRBCZMOOMBSQ-CCEZHUSRSA-N

General description

N-(p-Amylcinnamoyl)anthranilic acid (ACA) functions as a broad spectrum phospholipase A2 inhibitor and blocks transient receptor potential (TRP) channels. It inhibits calcium activated chloride current in cardiac ventricular myocytes. ACA regulates various ion channels.

Application

N-(p-Amylcinnamoyl)anthranilic acid has been used as a transient receptor potential cation channel subfamily M member 2 (TRPM2) inhibitor, in studying its role in regulating the production of reactive oxygen species (ROS).
N-(p-Amylcinnamoyl)anthranilic acid is a broad spectrum PLA2 inhibitor and TRP channel blocker. N-(p-Amylcinnamoyl)anthranilic acid has been used to study the functional expression of TRPM2 channels in dopaminergic SNc neurons.

Biochem/physiol Actions

Broad spectrum phospholipase A2 (PLA2) inhibitor and TRP channel blocker.

Features and Benefits

This compound is featured on the Phospholipase A2 page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000274463
0000164386
0000164385
026M4753V
125M4732V

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Bo Pang et al.
Pflugers Archiv : European journal of physiology, 463(2), 309-318 (2011-10-25)
Sustained increase in [Ca(2+)](c) (Δ[Ca(2+)](c)) is a critical early signal from T-cell receptor (TCR/CD3). In general, Ca(2+)-release activated Ca(2+) channels (CRAC) are responsible for the Ca(2+) influx and Δ[Ca(2+)](c) after TCR/CD3 stimulation. However, T cells also express Ca(2+)-permeable nonselective cation
N-(p-amylcinnamoyl) anthranilic acid (ACA): a phospholipase A2 inhibitor and TRP channel blocker
Harteneck C, et al.
Cardiovascular Drug Reviews, 25(1), 61-75 (2007)
A dual role of transient receptor potential melastatin 2 channel in cytotoxicity induced by silica nanoparticles
Yu P, et al.
Scientific Reports, 5, 18171-18171 (2015)
M Göl et al.
Archives italiennes de biologie, 157(1), 24-36 (2019-05-22)
N-(p-amylcinnamoyl) anthranilic acid (ACA) is a blocker of transient receptor potential melastatin-2 (TRPM2) which is a non-selective, Ca2+-permeable and oxidative stress sensor cation channel. Intracerebroventricular (ICV) streptozotocin (STZ) induction successfully generates spatial memory deficits in rats. The purpose of this
Mathias Gelderblom et al.
Stroke, 45(11), 3395-3402 (2014-09-23)
Brain injury during stroke results in oxidative stress and the release of factors that include extracellular Ca(2+), hydrogen peroxide, adenosine diphosphate ribose, and nicotinic acid adenine dinucleotide phosphate. These alterations of the extracellular milieu change the activity of transient receptor
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