5835-26-7

Basic information

• Product Name: ISOPIMARIC ACID
• Synonyms: 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
• CAS NO: 5835-26-7
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.455
• EINECS: 200-258-5
• Product Categories: Monovalent Ion Channels;Potassium Channel Modulators;Voltage-gated Ion Channels;Activators;Aliphatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5835-26-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 160°
• Boiling Point: 383.47°C (rough estimate)
• Flash Point: 200°C
• Appearance: white/solid
• Density: 1.0434 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4980 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO: ~26 mg/mL
• PKA: 4?+-.0.60(Predicted)
• Stability: Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: ISOPIMARIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPIMARIC ACID(5835-26-7)
• EPA Substance Registry System: ISOPIMARIC ACID(5835-26-7)

Safety Data

• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 5835-26-7(Hazardous Substances Data)

Usage

Description

Isopimaric acid is a terpenoid acid that exhibits a range of biological activities, including the activation of BK (voltage-gated potassium) channels, improvement of spatial and non-spatial memory in Alzheimer's mouse models, and enhancement of motor function in rat spinal cord injury models. It also reduces hyperactivity of spontaneously active auditory networks.

Uses

Used in Pharmaceutical Industry:
Isopimaric acid is used as a potent novel activator of large-conductance Ca2+-activated K+ channels for its potential therapeutic applications in various conditions, such as Alzheimer's disease and spinal cord injuries. Its ability to improve memory and motor function, as well as reduce hyperactivity in auditory networks, makes it a promising candidate for further research and development in the pharmaceutical field.

Biochem/physiol Actions

Potent opener of large conductance calcium activated K+ (BK) channels.

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

InChI:InChI=1/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

Upstream product

• 56-40-6 glycine 

Downstream Products

• 1686-64-2 pimara-7,15-dien-18-ol 
• 7716-07-6 (13S)-10-hydroxy-5β,10α-ros-15-en-18-oic acid-lactone 
• 514-10-3 abietic acid 
• 1686-62-0 Methyl isopimarate 
• 142699-20-5 (2S,4aS,4bR,8R,8aR)-2,4b,8-Trimethyl-8-phenylsulfanylmethyl-2-vinyl-1,2,3,4,4a,4b,5,6,7,8,8a,9-dodecahydro-phenanthrene 
• 1686-66-4 isopimara-7,15-diene 
• 19907-21-2 Methyl isopimara-8,15-dien-18-oate 
• 80692-85-9 (1R,3R,4aR,4bS,7S,10aR)-3-Hydroxy-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-phenanthrene-1-carboxylic acid 
• 80703-93-1 (1R,4aR,4bS,7S,10aR)-7-(1,2-Dihydroxy-ethyl)-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-phenanthrene-1-carboxylic acid 
• 80692-86-0 (1R,3R,4aR,4bS,7S,10aR)-7-(1,2-Dihydroxy-ethyl)-3-hydroxy-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-phenanthrene-1-carboxylic acid 
• 1686-62-0 isopimaric acid methyl ester 
• 40062-06-4 N-((1R,4aR,4bS,7S,10aR)-1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydro-phenanthren-1-yl)-benzamide