10-alpha-H-Ambros-11(13)-en-12-oic acid, 1,6-beta-dihydroxy-4-oxo-, gamma-lactone

Base Information

• Chemical Name: 10-alpha-H-Ambros-11(13)-en-12-oic acid, 1,6-beta-dihydroxy-4-oxo-, gamma-lactone
• CAS No.: 2571-81-5
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 2571-81-5.mol

Synonyms:Coronopolin;NSC 85242;10-alpha-H-Ambros-11(13)-en-12-oic acid, 1,6-beta-dihydroxy-4-oxo-, gamma-lactone;Azuleno(4,5-b)furan-2,9-dione, decahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, (3aS-(3aalpha,6beta,6aalpha,9abeta,9balpha))-

Chemical Property of 10-alpha-H-Ambros-11(13)-en-12-oic acid, 1,6-beta-dihydroxy-4-oxo-, gamma-lactone

Chemical Property:

• Vapor Pressure: 5.57E-10mmHg at 25°C
• Boiling Point: 449.8°C at 760 mmHg
• Flash Point: 168.8°C
• PSA: 63.60000
• Density: 1.22g/cm³
• LogP: 1.61440
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 264.13615911
• Heavy Atom Count: 19
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C3(C1(CCC3=O)O)C)OC(=O)C2=C
• Isomeric SMILES: C[C@H]1CC[C@@H]2[C@H]([C@]3([C@@]1(CCC3=O)O)C)OC(=O)C2=C
• General Description: Coronopilin is a pseudoguaianolide compound derived from *Parthenium hysterophorus*, structurally characterized as a sesquiterpene lactone with anti-inflammatory properties. Studies indicate that its derivatives, particularly those modified to lack an α-methylene group, exhibit enhanced inhibition of pro-inflammatory cytokines (TNF-α, IL-1β, and IL-6) in murine neutrophils, suggesting its potential as a scaffold for developing anti-inflammatory therapeutics.

Refernces

Psilostachyin, acetylated pseudoguaianolides and their analogues: Preparation and evaluation of their anti-inflammatory potential

10.1016/j.bmcl.2011.06.037

The research focuses on the synthesis and evaluation of the anti-inflammatory potential of naturally occurring acetylated pseudoguaianolides, psilostachyin, and their analogues. The study involved the isolation of parthenin and coronopilin from Parthenium hysterophorus, followed by their semi-synthesis to produce various derivatives. The anti-inflammatory activity was assessed through the in vitro expression of TNF-α, IL-1β, and IL-6 in murine neutrophils. Reactants used in the synthesis included parthenin, coronopilin, acetic anhydride, propionic anhydride, butyric anhydride, and InCl3 as a catalyst, among others. Analytical techniques employed included X-ray crystallography for structural confirmation and flow cytometry for cytokine expression analysis. The experiments revealed that some analogues, particularly those without an α-methylene moiety, displayed improved anti-inflammatory activity compared to the parent molecules, indicating their potential as therapeutic agents.

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