Micheliolide

Base Information

• Chemical Name: Micheliolide
• CAS No.: 68370-47-8
• Molecular Formula: C15H20O3
• Molecular Weight: 248.32
• DSSTox Substance ID: DTXSID20331787
• Nikkaji Number: J19.496D
• Wikidata: Q27107361
• Pharos Ligand ID: GCV3RUKRNLJN
• ChEMBL ID: CHEMBL449579
• Mol file: 68370-47-8.mol

Synonyms:micheliolide

Chemical Property of Micheliolide

Chemical Property:

• Vapor Pressure: 4.78E-09mmHg at 25°C
• Melting Point: 131-133 °C
• Boiling Point: 426.1°C at 760 mmHg
• PKA: 14.65±0.40(Predicted)
• Flash Point: 181.8°C
• PSA: 46.53000
• Density: 1.17g/cm³
• LogP: 2.35550
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 248.14124450
• Heavy Atom Count: 18
• Complexity: 462

Purity/Quality:

≥98% ^*data from raw suppliers

Micheliolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2CCC(C2C3C(CC1)C(=C)C(=O)O3)(C)O
• Isomeric SMILES: CC1=C2CC[C@@]([C@@H]2[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)(C)O
• Uses: Micheliolide, a sesquiterpene lactone is used in the inhibition of resistant acute leukemic cells. Selectively targets cancer stem and progenitor cells.

Technology Process of Micheliolide

There total 10 articles about Micheliolide 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: 91.0%

parthenolide (503551-53-9) → (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one (68370-47-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃;

Reference yield: 90.0%

5β-epoxy-germacra-1-(10),11-(13)-dien-12,6α-olide → (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one (68370-47-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.3390/molecules181013061

Reference yield: 78.0%

parthenolide → (3aS,9R,9aS,9bS)-9-hydroxy-6,9-dimethyl-3-methylene-3a,4,5,7,8,9,9a,9b-octahydroazuleno[4,5-b]furan-2(3H)-one (68370-47-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1002/anie.202106654

upstream raw materials:

methanol

parthenolide

11βH,13-dihydro-13-dimethylaminomicheliolide hydrochloride

11βH,13-dihydro-13-dimethylaminomicheliolide

Refernces

• 1、 Liu, Jie,Flegel, Jana,Otte, Felix,Pahl, Axel,Sievers, Sonja,Strohmann, Carsten,Waldmann, Herbert. "Combination of Pseudo-Natural Product Design and Formal Natural Product Ring Distortion Yields Stereochemically and Biologically Diverse Pseudo-Sesquiterpenoid Alkaloids". supporting information. p. 21384 - 21395. Retrieved 2021/08/23.
• 2、 Chen, Hao,Hu, Wenhui,Ou, Yitao,Sun, Ping,Wu, Dan,Wu, Nannan,Yang, Zhongjin. "Synthesis and biological evaluation of parthenolide derivatives with reduced toxicity as potential inhibitors of the NLRP3 inflammasome". supporting information. . Retrieved 2020/07/16.