ISOPIMARIC ACID

Product Name: ISOPIMARIC ACID
CAS No.: 5835-26-7
Chemical Name: ISOPIMARIC ACID
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
CBNumber: CB1503654
Molecular Formula: C20H30O2
Formula Weight: 302.45
MOL File: 5835-26-7.mol

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ISOPIMARIC ACID Property

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)

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Safety

RIDADR: UN 3077 9 / PGIII
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Warning
Hazard statements: H400Very toxic to aquatic life
Precautionary statements: P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: I6783
Product name: Isopimaric Acid
Purity: ≥98% (GC), powder
Packaging: 5mg
Price: $140.6
Updated: 2025/07/31

Sigma-Aldrich

Product number: I6783
Product name: Isopimaric Acid
Purity: ≥98% (GC), powder
Packaging: 25mg
Price: $571
Updated: 2025/07/31

TRC

Product number: I821940
Product name: Isopimaric Acid
Packaging: 100mg
Price: $1390
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FI24693
Product name: Isopimaric acid
Packaging: 1mg
Price: $65
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FI24693
Product name: Isopimaric acid
Packaging: 2mg
Price: $100
Updated: 2021/12/16

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ISOPIMARIC ACID Chemical Properties,Usage,Production

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

ISOPIMARIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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ISOPIMARIC ACID Suppliers

Canada 1 China 67 India 1 Switzerland 1 United Kingdom 1 United States 7 Global 78

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Sigma-Aldrich

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View Lastest Price from ISOPIMARIC ACID manufacturers

Career Henan Chemical Co

Product: ISOPIMARIC ACID 5835-26-7
Price: US $1.00/KG
Min. Order: 1KG
Purity: 95--99%
Supply Ability: 1ton
Release date: 2020-01-03

5835-26-7, ISOPIMARIC ACIDRelated Search:

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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

13-Methyl-17-norabieta-7,15-diene-18-oic acid

13β-Methyl-13-vinylpodocarp-7-en-18-oic acid

(-)-13β-Methyl-13-vinylpodocarp-7-en-15-oic 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

7,15-IsopiMaradien-18-oic Acid

Δ7,15-IsopiMaric Acid

(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

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)-

isopimaricaci

5835-26-7

Activators

Aliphatics

Chiral Reagents

Intermediates & Fine Chemicals

Pharmaceuticals

Monovalent Ion Channels

Potassium Channel Modulators

Voltage-gated Ion Channels