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

form 

solid

pka

4?+-.0.60(Predicted)

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)

Safety Information

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

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