| Identification | Back Directory | [Name]
ACA | [CAS]
110683-10-8 | [Synonyms]
ACA
4-amylcinnamoylanthranilicacid
N-(P-AMYLCINNAMOYL)ANTHRANILIC ACID
N-(p-Amylcinnamoyl) anthranilic Acid (ACA)
2-(3-(4-Pentylphenyl)acrylamido)benzoic acid
2-[[(E)-3-(4-PENTYLPHENYL)PROP-2-ENOYL]AMINO]BENZOIC ACID
Benzoic acid, 2-[[1-oxo-3-(4-pentylphenyl)-2-propen-1-yl]amino]- | [Molecular Formula]
C21H23NO3 | [MDL Number]
MFCD00211365 | [MOL File]
110683-10-8.mol | [Molecular Weight]
337.41 |
| Chemical Properties | Back Directory | [Melting point ]
172-174℃ | [Boiling point ]
563.1±50.0 °C(Predicted) | [density ]
1.178±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly) | [form ]
White solid. | [pka]
3.49±0.36(Predicted) | [color ]
White to Off-White |
| Hazard Information | Back Directory | [Uses]
N-(p-amylcinnamoyl) Anthranilic acid (ACA) is a channel blocker that acts on several transient receptor potential (TRP) channels, including TRPM2, TRPM8, and TRPC6 (IC50 = 1.7, 3.8, and 2.3 μM, respectively). It is a weak inhibitor of TRPV1. ACA is also an inhibitor of phospholipase A2, blocking the release of arachidonic acid when given at 50 μM. | [Definition]
ChEBI:N-(p-amylcinnamoyl)anthranilic acid is an amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 4-pentylcinnamoyl group. It is a transient receptor potential (TRP) channel blocker and phospholipase A2 (PLA2) inhibitor. It has a role as an EC 3.1.1.4 (phospholipase A2) inhibitor and a TRP channel blocker. It is an amidobenzoic acid, a member of cinnamamides and a secondary carboxamide. | [Biological Activity]
n-(p-amylcinnamoyl) anthranilic acid (aca) is a broad-spectrum phospholipase a2 (pla2) inhibitor and trp channel blocker [1] [2].pla2 enzymes are a family of structurally different enzymes including at least nine subfamilies. the mammalian trp proteins including at least 27 members and can be grouped into trpc, trpv, trpm, trpa, trpp, and trpml six subfamilies [1].n-(p-amylcinnamoyl) anthranilic acid (aca) is a broad-spectrum pla2 inhibitor and trp channel blocker [1] [2]. in hek293 cells transfected with human trpm2, aca (20 ?m) completely blocked h2o2-induced ca2+ signals and adpr-induced whole-cell currents with ic50 value of 1.7 ?m. aca (20 ?m) also blocked human trpm8-induced ca2+ signals and trpc6-mediated currents with ic50 values of 3.9 ?m and 2.3 ?m, respectively. aca can serve as a useful tool for studying the function of trpm2 in native cells [2]. in isolated pig cardiac ventricular myocytes, aca reversibly inhibited icl(ca) with ic50 value of 4.2 ?m in a concentration-dependent way. aca (50 ?m) also inhibited the camp-activated chloride current. | [storage]
Store at -20°C | [References]
harteneck c, frenzel h, kraft r. n-(p-amylcinnamoyl)anthranilic acid (aca): a phospholipase a(2) inhibitor and trp channel blocker. cardiovasc drug rev. 2007 spring;25(1):61-75.kraft r, grimm c, frenzel h, et al. inhibition of trpm2 cation channels by n-(p-amylcinnamoyl)anthranilic acid. br j pharmacol. 2006 jun;148(3):264-73.gwanyanya a, macianskiene r, bito v, 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. |
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