N-(p-amylcinnamoyl) Anthranilic Acid

Names

[ Name ]:
N-(p-amylcinnamoyl) Anthranilic Acid

[Synonym ]:
2-{[(2E)-3-(4-Pentylphenyl)-2-propenoyl]amino}benzoic acid
4-amylcinnamoylanthranilicacid
2-{[(2E)-3-(4-pentylphenyl)prop-2-enoyl]amino}benzoic acid
Benzoic acid, 2-[[(2E)-1-oxo-3-(4-pentylphenyl)-2-propen-1-yl]amino]-

Biological Activity

[Description]:

N-(p-amylcinnamoyl) Anthranilic Acid (ACA) is a broad spectrum Phospholipase A2 (PLA2) inhibitor and TRP channel blocker[1][2]. N-(p-amylcinnamoyl) Anthranilic Acid (ACA) is also an effective reversible inhibitor of calcium-activated chloride channels, has potential to treat arrhythmia[3].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase

[Target]

PLA2[1][2]. TRP channel[1][2].Calcium-activated chloride channels[3].

[In Vitro]

N-(p-amylcinnamoyl) Anthranilic Acid (ACA; 20 μM) completely blocks ADPR-induced whole-cell currents and H2O2-induced Ca2+ signals (IC50=1.7 μM) in HEK293cells transfected with human TRPM2[1]. N-(p-amylcinnamoyl) Anthranilic Acid (ACA; 20 μM) also blocks currents through human TRPM8 and TRPC6 expressed in HEK293 cells[1]. N-(p-amylcinnamoyl) Anthranilic Acid (ACA) modulates the activity of different TRP channels independent of PLA22 inhibition[1].

[References]

[1]. Kraft R, et al. Inhibition of TRPM2 cation channels by N-(p-amylcinnamoyl)anthranilic acid. Br J Pharmacol. 2006 Jun;148(3):264-73.

[2]. Harteneck C, et al. N-(p-amylcinnamoyl)anthranilic acid (ACA): a phospholipase A(2) inhibitor and TRP channel blocker. Cardiovasc Drug Rev. 2007 Spring;25(1):61-75.

[3]. Gwanyanya A, et al. Inhibition of the calcium-activated chloride current in cardiac ventricular myocytes by N-(p-amylcinnamoyl)anthranilic acid (ACA). Biochem Biophys Res Commun. 2010 Nov 19;402(3):531-6.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
563.1±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₂₃NO₃

[ Molecular Weight ]:
337.41

[ Flash Point ]:
294.4±30.1 °C

[ Exact Mass ]:
337.167786

[ PSA ]:
66.40000

[ LogP ]:
7.11

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.629

[ Storage condition ]:
-20℃

Safety Information

[ HS Code ]:
2924299090

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%