Isopimaric acid

Base Information

• Chemical Name: Isopimaric acid
• CAS No.: 5835-26-7
• Deprecated CAS: 7201-52-7,107631-59-4
• Molecular Formula: C20H30 O2
• Molecular Weight: 302.457
• European Community (EC) Number: 635-236-9
• UNII: 1E37K85HHK
• DSSTox Substance ID: DTXSID9022233
• Nikkaji Number: J8.075F
• Wikipedia: Isopimaric_acid
• Wikidata: Q4198762
• Metabolomics Workbench ID: 28532
• ChEMBL ID: CHEMBL512164
• Mol file: 5835-26-7.mol

Synonyms:4-epi-isopimaric acid;isopimaric acid

Chemical Property of Isopimaric acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 160°
• Refractive Index: 1.4980 (estimate)
• Boiling Point: 416.7°Cat760mmHg
• PKA: 4?+-.0.60(Predicted)
• Flash Point: 200°C
• PSA: 37.30000
• Density: 1.05g/cm³
• LogP: 5.20620
• Storage Temp.: −20°C
• Solubility.: DMSO: ~26 mg/mL
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 302.224580195
• Heavy Atom Count: 22
• Complexity: 534

Purity/Quality:

98%,99%, ^*data from raw suppliers

Isopimaric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCC2C(=CCC3C2(CCCC3(C)C(=O)O)C)C1)C=C
• Isomeric SMILES: C[C@@]1(CC[C@H]2C(=CC[C@@H]3[C@@]2(CCC[C@@]3(C)C(=O)O)C)C1)C=C
• 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.

Technology Process of Isopimaric acid

There total 3 articles about Isopimaric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

isopimaric acid chloride + glycine (56-40-6,18875-39-3,25718-94-9) → isopimaric acid (5835-26-7) + C22H33NO3

Guidance literature:

With potassium carbonate; potassium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 72h;

DOI:10.1007/s10600-021-03391-1

Reference yield:

→ isopimaric acid (514-08-9,5835-26-7,19941-42-5,30951-15-6,94450-35-8,115333-97-6,141474-11-5)

Guidance literature:

entsprech. Methylester, Essigsaeure/Chinolin;

DOI:10.1055/s-1975-23750

Reference yield:

→ isopimaric acid (5835-26-7)

Guidance literature:

DOI:10.1139/v65-171

upstream raw materials:

glycine

Downstream raw materials:

Methyl isopimara-8,15-dien-18-oate

Refernces

• 1、 Baev, D. S.,Borisov, S. A.,Gromova, M. A.,Kharitonov, Yu. V.,Shul’ts, E. E.,Tolstikova, T. G.. "Synthetic Transformations of Higher Terpenoids. 39.? Synthesis and Analgesic Activity of Isopimaric Acid Derivatives". . . Retrieved 2021.