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| | ISOPIMARIC ACID 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: | 5835-26-7 | | MF: | C20H30O2 | | MW: | 302.45 | | EINECS: | 200-258-5 | | Product Categories: | Activators;Aliphatics;Monovalent Ion Channels;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Potassium Channel Modulators;Voltage-gated Ion Channels | | Mol File: | 5835-26-7.mol |  |
| | ISOPIMARIC ACID Chemical Properties |
| Melting point | 160° | | alpha | D16 -3.6° (10.4% soln in 1:1 alcohol:chloroform) | | Boiling point | 383.47°C (rough estimate) | | density | 1.0434 (rough estimate) | | refractive index | 1.4980 (estimate) | | storage temp. | -20°C | | solubility | DMSO: ~26 mg/mL | | pka | 4?+-.0.60(Predicted) | | form | solid | | color | white | | Stability: | Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. | | EPA Substance Registry System | Isopimaric acid (5835-26-7) |
| RIDADR | UN 3077 9 / PGIII | | WGK Germany | 3 |
| | ISOPIMARIC ACID Usage And Synthesis |
| 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. | | Definition | ChEBI: Isopimaric acid is a diterpenoid, a carbotricyclic compound and a monocarboxylic acid. It is a conjugate acid of an isopimarate. It derives from a hydride of an isopimara-7,15-diene. | | 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 |
| | ISOPIMARIC ACID Preparation Products And Raw materials |
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