Parthenicin

Base Information

• Chemical Name: Parthenicin
• CAS No.: 508-59-8
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• NSC Number: 85239
• DSSTox Substance ID: DTXSID60871713
• Wikidata: Q105153663
• ChEMBL ID: CHEMBL1869439
• Mol file: 508-59-8.mol

Synonyms:Parthenicin;MLS002694604;NSC85239;SMR001560529;6a-hydroxy-6,9a-dimethyl-3-methylidene-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-dione;6a-hydroxy-6,9a-dimethyl-3-methylene-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-dione;NSC-85239;6a-Hydroxy-6,9a-dimethyl-3-methylene-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,9-dione;cid_257275;CHEMBL1869439;BDBM97034;DTXSID60871713;NCGC00246887-01;NCI60_041873;10.alpha.H-Ambrosa-2, 1,6.beta.-dihydroxy-4-oxo-, .gamma.-lactone;6,9a-dimethyl-3-methylidene-6a-oxidanyl-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-dione;6a-hydroxy-6,9a-dimethyl-3-methylene-4,5,6,9b-tetrahydro-3aH-azuleno[8,7-b]furan-2,9-quinone;6a-Hydroxy-6,9a-dimethyl-3-methylidene-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,9-dione;Azuleno[4,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6a-hydroxy-6,9a-dimethyl-3-methylene-, [3aS-(3a.alpha.,6.beta.,6a.alpha.,9a.beta.,9b.alpha.)]-

Chemical Property of Parthenicin

Chemical Property:

• Vapor Pressure: 1.12E-10mmHg at 25°C
• Melting Point: 163-166°
• Refractive Index: 1.4300 (estimate)
• Boiling Point: 466.9°C at 760 mmHg
• PKA: 12.69±0.60(Predicted)
• Flash Point: 177.3°C
• PSA: 63.60000
• Density: 1.25g/cm³
• LogP: 1.39040
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 262.12050905
• Heavy Atom Count: 19
• Complexity: 520

Purity/Quality:

98%min ^*data from raw suppliers

PARTHENIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2C(C3(C1(C=CC3=O)O)C)OC(=O)C2=C

Technology Process of Parthenicin

There total 3 articles about Parthenicin 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:

3-Dimethylamino-2-((3aR,4R,5S)-4-hydroxy-3a,8-dimethyl-3-oxo-3,3a,4,5,6,7-hexahydro-azulen-5-yl)-N,N-dimethyl-propionamide (125116-25-8) → parthenin (508-59-8,20555-04-8,69401-55-4,69401-56-5,93665-22-6)

Guidance literature:

With sodium hydrogencarbonate; methyl iodide; 1) 5 h, 2) 24 h;

Reference yield:

magnesium methyl carbonate (4861-79-4) + (3aS,6S,6aR,7S,9aR,9bR)-6a,7-epoxy-6,9a-dimethyl-3,3a,4,5,6,6a,7,8,9a,9b-decahydroazureno<4,5-b>furan-2,9-dione 9-ethylen acetal → parthenin (508-59-8,20555-04-8,69401-55-4,69401-56-5,93665-22-6)

Guidance literature:

With formaldehyd; sodium acetate; acetic acid; diethylamine; Yield given. Multistep reaction; 1.) DMF, 140 degC, 3 h; 2.) 110 degC, 15 min;

DOI:10.1016/0040-4020(95)00068-J

Reference yield:

→ (+/-)-Hyruenin (508-59-8,20555-04-8,69401-55-4,69401-56-5,93665-22-6)

Guidance literature:

Neoambrosin 7, m-Chlorperbenzoesaeure, ????;

upstream raw materials:

3-Dimethylamino-2-((3aR,4R,5S)-4-hydroxy-3a,8-dimethyl-3-oxo-3,3a,4,5,6,7-hexahydro-azulen-5-yl)-N,N-dimethyl-propionamide

magnesium methyl carbonate

Downstream raw materials:

neoambrosin

anhydroparthenin

C₂₂H₂₆O₄

C₂₂H₂₆O₄

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.