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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

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

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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Anthranilic acid reagent grade, ≥98%

Sigma-Aldrich

A89855

Anthranilic acid

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
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)
Aminobenzoic Acids-Advances in Research and Application (2012)
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
Ramazan Bal et al.
European journal of pharmacology, 882, 173163-173163 (2020-06-03)
Oxidative stress-induced Ca2+ permeable transient receptor potential melastatin 2 (TRPM2) channels are expressed at high levels in the brain, appear to link neuronal excitability to cellular metabolism, and are involved in the pathogenesis of neurodegenerative disorders. We aimed to study
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Phospholipase A2

Phospholipase A2 (PLA2) enzymes hydrolyze glycerophospholipids, yielding arachidonic acid; inhibition targets eicosanoid biosynthesis.

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