Isopimaric Acid
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MedKoo CAT#: 464996

CAS#: 5835-26-7

Description: Isopimaric acid is a diterpenoid resin acid that has been found in P. nigra and has diverse biological activities. It is active against clinical isolates of epidemic methicillin-resistant S. aureus (EMRSA; MICs = 32-64 µg/ml). 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). 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. 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.

Chemical Structure

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Isopimaric Acid
CAS# 5835-26-7
Instruction

Theoretical Analysis

MedKoo Cat#: 464996
Name: Isopimaric Acid
CAS#: 5835-26-7
Chemical Formula: C20H30O2
Exact Mass: 302.22
Molecular Weight: 302.458
Elemental Analysis: C, 79.42; H, 10.00; O, 10.58

Price and Availability

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5mg USD 350 2 Weeks
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Synonym: Isopimaric Acid; 7,15-Isopimaradien-18-oic Acid; (+)-Isopimaric Acid; (+) Isopimaric Acid;

IUPAC/Chemical Name: (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

InChi Key: MXYATHGRPJZBNA-KRFUXDQASA-N

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

SMILES Code: C[C@]12[C@]([H])([C@@](CCC2)(C(O)=O)C)CC=C3[C@@]1(CC[C@@](C3)(C=C)C)[H]

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 302.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Smith E, Williamson E, Zloh M, Gibbons S. Isopimaric acid from Pinus nigra shows activity against multidrug-resistant and EMRSA strains of Staphylococcus aureus. Phytother Res. 2005 Jun;19(6):538-42. doi: 10.1002/ptr.1711. PMID: 16114093.

2: Lu YJ, Zhao ZD, Chen YX, Wang J, Xu SC, Gu Y. Synthesis and biological activity of pyridine acylhydrazone derivatives of isopimaric acid. J Asian Nat Prod Res. 2021 Jun;23(6):545-555. doi: 10.1080/10286020.2020.1810668. Epub 2020 Aug 28. PMID: 32856467.

3: Gnanasekaran T, Vavitsas K, Andersen-Ranberg J, Nielsen AZ, Olsen CE, Hamberger B, Jensen PE. Heterologous expression of the isopimaric acid pathway in Nicotiana benthamiana and the effect of N-terminal modifications of the involved cytochrome P450 enzyme. J Biol Eng. 2015 Dec 22;9:24. doi: 10.1186/s13036-015-0022-z. PMID: 26702299; PMCID: PMC4688937.

4: Salari S, Silverå Ejneby M, Brask J, Elinder F. Isopimaric acid - a multi- targeting ion channel modulator reducing excitability and arrhythmicity in a spontaneously beating mouse atrial cell line. Acta Physiol (Oxf). 2018 Jan;222(1). doi: 10.1111/apha.12895. Epub 2017 Jun 9. PMID: 28514017.

5: Gromova MA, Kharitonov YV, Bagryanskaya IY, Shults EE. Efficient Synthesis of the N-(buta-2,3-dienyl)carboxamide of Isopimaric Acid and the Potential of This Compound towards Heterocyclic Derivatives of Diterpenoids. ChemistryOpen. 2018 Nov 14;7(11):890-901. doi: 10.1002/open.201800205. PMID: 30460170; PMCID: PMC6234760.

6: Wilson AE, Moore ER, Mohn WW. Isolation and characterization of isopimaric acid-degrading bacteria from a sequencing batch reactor. Appl Environ Microbiol. 1996 Sep;62(9):3146-51. doi: 10.1128/aem.62.9.3146-3151.1996. PMID: 8795202; PMCID: PMC168108.

7: Goels T, Eichenauer E, Langeder J, Hoeller F, Sykora C, Tahir A, Urban E, Heiss EH, Saukel J, Glasl S. Norway Spruce Balm: Phytochemical Composition and Ability to Enhance Re-epithelialization In Vitro. Planta Med. 2020 Oct;86(15):1080-1088. doi: 10.1055/a-1141-0921. Epub 2020 Apr 21. PMID: 32316044.

8: Saleh SN, Angermann JE, Sones WR, Leblanc N, Greenwood IA. Stimulation of Ca2+-gated Cl- currents by the calcium-dependent K+ channel modulators NS1619 [1 ,3-dihydro-1-[2-hydroxy-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2H-benzim idazol-2-one] and isopimaric acid. J Pharmacol Exp Ther. 2007 Jun;321(3):1075-84. doi: 10.1124/jpet.106.118786. Epub 2007 Mar 8. PMID: 17347326.

9: Cámara B, Strömpl C, Verbarg S, Spröer C, Pieper DH, Tindall BJ. Pseudomonas reinekei sp. nov., Pseudomonas moorei sp. nov. and Pseudomonas mohnii sp. nov., novel species capable of degrading chlorosalicylates or isopimaric acid. Int J Syst Evol Microbiol. 2007 May;57(Pt 5):923-931. doi: 10.1099/ijs.0.64703-0. PMID: 17473234.

10: Janocha S, Zapp J, Hutter M, Kleser M, Bohlmann J, Bernhardt R. Resin acid conversion with CYP105A1: an enzyme with potential for the production of pharmaceutically relevant diterpenoids. Chembiochem. 2013 Mar 4;14(4):467-73. doi: 10.1002/cbic.201200729. Epub 2013 Feb 1. PMID: 23371760.

11: Sadgrove NJ, Senbill H, Van Wyk BE, Greatrex BW. New Labdanes with Antimicrobial and Acaricidal Activity: Terpenes of Callitris and Widdringtonia (Cupressaceae). Antibiotics (Basel). 2020 Apr 11;9(4):173. doi: 10.3390/antibiotics9040173. PMID: 32290471; PMCID: PMC7235842.

12: Zhao ZD, Chen YX, Wang YM, Bi LW. 1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodeca-hydro- phenanthrene-1-carboxylic acid. Acta Crystallogr Sect E Struct Rep Online. 2009 May 29;65(Pt 6):o1429. doi: 10.1107/S1600536809019308. PMID: 21583270; PMCID: PMC2969610.

13: Geisler K, Jensen NB, Yuen MM, Madilao L, Bohlmann J. Modularity of Conifer Diterpene Resin Acid Biosynthesis: P450 Enzymes of Different CYP720B Clades Use Alternative Substrates and Converge on the Same Products. Plant Physiol. 2016 May;171(1):152-64. doi: 10.1104/pp.16.00180. Epub 2016 Mar 2. PMID: 26936895; PMCID: PMC4854711.

14: Kutney JP, Berset JD, Hewitt GM, Singh M. Biotransformation of Dehydroabietic, Abietic, and Isopimaric Acids by Mortierella isabellina Immobilized in Polyurethane Foam. Appl Environ Microbiol. 1988 Apr;54(4):1015-22. doi: 10.1128/aem.54.4.1015-1022.1988. PMID: 16347596; PMCID: PMC202589.

15: Wu XW, Wang Q, Li Q, Cui YM, Pu YK, Shi QQ, Bi DW, Zhang JJ, Zhang RH, Li XL, Zhang XJ, Xiao WL. Rubellawus A-D, Four New Diterpenoids Isolated from Callicarpa rubella and Their Anti-NLRP3 Inflammasome Effects. Chem Biodivers. 2020 Dec;17(12):e2000798. doi: 10.1002/cbdv.202000798. Epub 2020 Nov 26. PMID: 33135326.

16: Abdel-Kader MS, Hamad AM, Alanazi MT, Alanazi AH, Ali R, Foudah AI, Alqarni MH. Characterization and hepatoprotective evaluation of sesquiterpenes and diterpenes from the aerial parts of Juniperus sabina L. Saudi Pharm J. 2019 Nov;27(7):920-929. doi: 10.1016/j.jsps.2019.06.006. Epub 2019 Jun 22. PMID: 31997898; PMCID: PMC6978623.

17: Chiu CC, Keeling CI, Henderson HM, Bohlmann J. Functions of mountain pine beetle cytochromes P450 CYP6DJ1, CYP6BW1 and CYP6BW3 in the oxidation of pine monoterpenes and diterpene resin acids. PLoS One. 2019 May 9;14(5):e0216753. doi: 10.1371/journal.pone.0216753. PMID: 31071168; PMCID: PMC6508646.

18: Janocha S, Carius Y, Hutter M, Lancaster CR, Bernhardt R. Crystal Structure of CYP106A2 in Substrate-Free and Substrate-Bound Form. Chembiochem. 2016 May 3;17(9):852-60. doi: 10.1002/cbic.201500524. Epub 2016 Mar 11. PMID: 26864272.

19: Timoshenko MA, Kharitonov YV, Shakirov MM, Bagryanskaya IY, Shults EE. Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives. ChemistryOpen. 2015 Oct 28;5(1):65-70. doi: 10.1002/open.201500187. PMID: 27308214; PMCID: PMC4906488.

20: Wu C, V Gopal K, Lukas TJ, Gross GW, Moore EJ. Pharmacodynamics of potassium channel openers in cultured neuronal networks. Eur J Pharmacol. 2014 Jun 5;732:68-75. doi: 10.1016/j.ejphar.2014.03.017. Epub 2014 Mar 25. PMID: 24681057.