5835-26-7

Basic information

• Product Name: ISOPIMARIC ACID
• Synonyms: 1-phenanthrenecarboxylicacid,7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahyd;7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-1-phenanthrenecarboxylicaci;13-Methyl-17-norabieta-7,15-diene-18-oic acid;13β-Methyl-13-vinylpodocarp-7-en-18-oic acid;(-)-13β-Methyl-13-vinylpodocarp-7-en-15-oic Acid;(1R,4aR,4bS,7S,10aR)-7-Ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-triMethyl-1-phenanthrenecarboxylic Acid;7,15-IsopiMaradien-18-oic Acid;Δ7,15-IsopiMaric Acid
• CAS NO: 5835-26-7
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.455
• EINECS: 200-258-5
• Product Categories: Monovalent Ion Channels;Potassium Channel Modulators;Voltage-gated Ion Channels;Activators;Aliphatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5835-26-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 160°
• Boiling Point: 383.47°C (rough estimate)
• Flash Point: 200°C
• Appearance: white/solid
• Density: 1.0434 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4980 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO: ~26 mg/mL
• PKA: 4?+-.0.60(Predicted)
• Stability: Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: ISOPIMARIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPIMARIC ACID(5835-26-7)
• EPA Substance Registry System: ISOPIMARIC ACID(5835-26-7)

Safety Data

• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 5835-26-7(Hazardous Substances Data)

Usage

Description

Isopimaric acid (5835-26-7) is a terpenoid acid that activates BK (voltage-gated potassium) channels when used at 10 μM in HEK293 cells.1 Improves spatial and non-spatial memory in Alzheimer’s mouse model2,3, and significantly improves motor function in a rat spinal cord injury model4. Reduces hyperactivity of spontaneously active auditory networks, EC50=7.8 μM.5

Uses

A potent novel activators of large-conductance Ca2+-activated K+ channel.

General Description

Isopimaric acid, a resin acid produced by conifer trees, is a tricyclic diterpene compound. High levels of isopimaric acid in the hepatocytes of the rainbow trout may impair calcium signalling machinery. Isopimaric acid is a potential big potassium (BK) channel opener.

Biochem/physiol Actions

Potent opener of large conductance calcium activated K+ (BK) channels.

References

Imaizumi et al. (2002), Molecular basis of pimarane compounds as novel activators of large-conductance CA(2+)-activated K(+) channel alpha-subunit; Mol. Pharmacol., 62 836 Wang et al. (2015), Cognitive recovery by chronic activation of the large-conductance calcium-activated potassium channel in a mouse model of Alzheimer’s disease; Neuropharmacology, 92 8 Wang et al. (2015), Improvement of spatial learning by facilitating large-conductance calcium-activated potassium channel with transcranial magnetic stimulation in Alzheimer’s disease model mice; Neuropharmacology, 97 210 Jacobsen et al. (2018), Activation of the Large-conductance, Voltage, and Ca2+-Activated K+ (BK) Channel in Acute Spinal Cord Injury in the Wistar Rat is Neuroprotective; Front. Neurol., 9 1107 Wu et al. (2014), Pharmacodynamics of potassium channel openers in cultured neuronal networks; Eur. J. Pharmacol., 732 68

InChI:InChI=1/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,7,15-16H,1,6,8-13H2,2-4H3,(H,21,22)/t15?,16?,18-,19+,20+/m0/s1

Upstream product

• 56-40-6 glycine 

Downstream Products

• 7715-73-3 8-isopimarenic acid