ISOPIMARIC ACID

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 Structure
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
pka4?+-.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 SystemIsopimaric acid (5835-26-7)
Safety Information
RIDADR UN 3077 9 / PGIII
WGK Germany 3
MSDS Information
ISOPIMARIC ACID Usage And Synthesis
DescriptionIsopimaric 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
UsesA potent novel activators of large-conductance Ca2+-activated K+ channel.
DefinitionChEBI: 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 DescriptionIsopimaric 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 ActionsPotent opener of large conductance calcium activated K+ (BK) channels.
ReferencesImaizumi 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
Preparation ProductsISOPIMAROL
2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one Hydroxyecdysone Imiquimod ISOLIQUIRITIN AZ20 (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one Artemether beta-Sitosterol hydroxygenkwanin 9-Cyclopentyl-2-[[2-methoxy-4-[(1-methylpiperidin-4-yl)oxy]-phenyl]amino]-7-methyl-7,9-dihydro-8H-purin-8-one ML335 alpha-Terpineol beta-Eudesmol MOSLOFLAVONE alpha-Cyperone

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