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.

InChI

InChI=1S/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

InChIKey

MXYATHGRPJZBNA-KRFUXDQASA-N

SMILES

[C@@]1(C)(C(O)=O)[C@@]2([H])[C@@](C)([C@]3([H])C(=CC2)C[C@](C=C)(C)CC3)CCC1

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

[1] YUJI IMAIZUMI. Molecular basis of pimarane compounds as novel activators of large-conductance Ca(2+)-activated K(+) channel alpha-subunit.[J]. Molecular Pharmacology, 2002, 62 4: 836-846. DOI:10.1124/mol.62.4.836
[2] LI WANG . Cognitive recovery by chronic activation of the large-conductance calcium-activated potassium channel in a mouse model of Alzheimer’s disease[J]. Neuropharmacology, 2015, 92: Pages 8-15. DOI:10.1016/j.neuropharm.2014.12.033
[3] FURONG WANG . Improvement of spatial learning by facilitating large-conductance calcium-activated potassium channel with transcranial magnetic stimulation in Alzheimer’s disease model mice[J]. Neuropharmacology, 2015, 97: Pages 210-219. DOI:10.1016/j.neuropharm.2015.05.027
[4] MARIANNE JACOBSEN. Activation of the Large-Conductance, Voltage, and Ca2+- Activated K+ (BK) Channel in Acute Spinal Cord Injury in the Wistar Rat Is Neuroprotective.[J]. Frontiers in Neurology, 2018: 1107. DOI:10.3389/fneur.2018.01107
[5] CALVIN WU . Pharmacodynamics of potassium channel openers in cultured neuronal networks[J]. European journal of pharmacology, 2014, 732: Pages 68-75. DOI:10.1016/j.ejphar.2014.03.017

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