CID 333544

Base Information

• Chemical Name: CID 333544
• CAS No.: 25127-29-1
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• NSC Number: 335648
• Nikkaji Number: J1.261.673B
• Wikidata: Q105279775
• Metabolomics Workbench ID: 126000
• ChEMBL ID: CHEMBL1989287
• Mol file: 25127-29-1.mol

Synonyms:crebanine;L-CBN;L-crebanine

Chemical Property of CID 333544

Chemical Property:

• Vapor Pressure: 1.11E-09mmHg at 25°C
• Melting Point: 126 °C
• Boiling Point: 488.2°Cat760mmHg
• PKA: 6?+-.0.20(Predicted)
• Flash Point: 145.4°C
• PSA: 40.16000
• Density: 1.266g/cm³
• LogP: 3.12250
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 502

Purity/Quality:

≥98% ^*data from raw suppliers

Crebanine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C4=C2C1CC5=C4C=CC(=C5OC)OC)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C4=C2[C@H]1CC5=C4C=CC(=C5OC)OC)OCO3
• Uses: Crebanine is an aporphine alkaloid which helps sensitize TNF-α induced apoptosis and suppress human lung adenocarcinoma. Known to exhibit anticancer properties.

Technology Process of CID 333544

There total 2 articles about CID 333544 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + stesakine (77784-23-7) → Crebanine (517-62-4,25127-29-1,79642-40-3)

Guidance literature:

In diethyl ether;

DOI:10.1016/S0031-9422(00)83953-9

Reference yield:

→ Crebanine (517-62-4,25127-29-1,79642-40-3)

Guidance literature:

With sulfuric acid; copper; anschliessend Erwaermen mit Zink-Pulver und wss. HCl;

Reference yield: 91.0%

(-)-crebanine (517-62-4,25127-29-1,79642-40-3) → dehydrocrebanine (77784-22-6)

Guidance literature:

With palladium 10% on activated carbon; In acetonitrile; for 6h; Inert atmosphere; Reflux;

DOI:10.3390/molecules21121555

upstream raw materials:

diazomethane

stesakine

Downstream raw materials:

dehydrocrebanine

stesakine