A diterpenoid resin acid
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Isopimaric Acid

Item No. 34544

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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
CAS Number
5835-26-7
Synonyms
  • 7,15-Isopimaradien-18-oic Acid
  • (+)-Isopimaric Acid
Molecular Formula
C20H30O2
Formula Weight
302.5
Purity
≥90%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleMethanol: Slightly soluble
SMILES
C[C@@]12[C@](CC=C3[C@]2([H])CC[C@@](C)(C3)C=C)([H])[C@@](C)(CCC1)C(O)=O
InChi Code
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
InChi Key
MXYATHGRPJZBNA-KRFUXDQASA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Isopimaric acid is a diterpenoid resin acid that has been found in P. nigra and has diverse biological activities.1,2,3,4 It is active against clinical isolates of epidemic methicillin-resistant S. aureus (EMRSA; MICs = 32-64 µg/ml).1 Isopimaric acid is an agonist of retinoid X receptor alpha (RXRα), RXRβ, and RXRγ in a reporter assay using HEK293T cells expressing human receptors (EC50s = 26, 32, and 33 µM, respectively).2 It opens large conductance calcium-activated potassium channels (BKCa1.1/KCa1.1) in HEK293 cells expressing recombinant channels and the activating β1 regulatory subunit when used at a concentration of 10 µM.3 Isopimaric acid potentiates reductions in field excitatory postsynaptic potential (fEPSP) slopes in hippocampal slices and decreases escape latency in the Morris water maze in a 3xTg mouse model of Alzheimer’s disease.4 It has been found as an environmental contaminant in pulp and paper mill effluent.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Smith, E., Williamson, E., Zloh, M., et al. Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus. Phytother. Res. 19(6), 538-542 (2005).

    2. Merk, D., Grisoni, F., Friedrich, L., et al. Computer-assisted discovery of retinoid X receptor modulating natural products and isofunctional mimetics. J. Med. Chem. 61(12), 5442-5447 (2018).

    3. Imaizumi, Y., Sakamoto, K., Yamada, A., et al. Molecular basis of pimarane compounds as novel activators of large-conductance Ca2+-activated K+ channel α-subunit. Mol. Pharmacol. 62(4), 836-846 (2002).

    4. Wang, L., Kang, H., Li, Y., et al. Cognitive recovery by chronic activation of the large-conductance calcium-activated potassium channel in a mouse model of Alzheimer’s disease. Neuropharmacology 92, 8-15 (2015).

    5. van den Heuvel, M.R., Ellis, R.J., Tremblay, L.A., et al. Exposure of reproductively maturing rainbow trout to a New Zealand pulp and paper mill effluent. Ecotoxicol. Environ. Saf. 51(1), 65-75 (2002).