| Identification | Back Directory | [Name]
ISOPIMARIC ACID | [CAS]
5835-26-7 | [Synonyms]
isopimaricaci
Δ7,15-IsopiMaric Acid
7,15-IsopiMaradien-18-oic Acid
13β-Methyl-13-vinylpodocarp-7-en-18-oic acid
13-Methyl-17-norabieta-7,15-diene-18-oic acid
(-)-13β-Methyl-13-vinylpodocarp-7-en-15-oic Acid
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
(1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene-1-carboxylic 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
1-Phenanthrenecarboxylic acid, 7-ethenyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-1,4a,7-trimethyl-, (1R,4aR,4bS,7S,10aR)- | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C20H30O2 | [MDL Number]
MFCD04113116 | [MOL File]
5835-26-7.mol | [Molecular Weight]
302.45 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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. | [storage]
-20°C | [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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