Thalicarpine

Base Information

• Chemical Name: Thalicarpine
• CAS No.: 5373-42-2
• Molecular Formula: C₄₁H₄₈N₂O₈
• Molecular Weight: 696.841
• NSC Number: 68075
• UNII: 8X1D791RF6
• DSSTox Substance ID: DTXSID90202011
• Nikkaji Number: J7.977D
• Wikidata: Q27108417
• NCI Thesaurus Code: C869
• Metabolomics Workbench ID: 53478
• ChEMBL ID: CHEMBL507100
• Mol file: 5373-42-2.mol

Synonyms:Thaliblastine;thalicarpine

Chemical Property of Thalicarpine

Chemical Property:

• Vapor Pressure: 3.91E-23mmHg at 25°C
• Melting Point: 160-161°
• Refractive Index: 1.4670 (estimate)
• Boiling Point: 762.2°Cat760mmHg
• Flash Point: 181.4°C
• PSA: 80.32000
• Density: 1.194g/cm³
• LogP: 6.93870
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 696.34106649
• Heavy Atom Count: 51
• Complexity: 1120

Purity/Quality:

99% ^*data from raw suppliers

THALICARPINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)OC5=CC(=C(C=C5CC6C7=CC(=C(C=C7CCN6C)OC)OC)OC)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)OC5=CC(=C(C=C5C[C@H]6C7=CC(=C(C=C7CCN6C)OC)OC)OC)OC)OC)OC
• Description: A complex alkaloid, thaliblastine occurs in Thalictrum minus elatum and has been assigned the structure given on the basis of chemical and spectroscopic investigations. The alkaloid has marked antitumour activity but rapid administration of the base causes brachycardia, hypotension and inhibition of respiration in laboratory animals. Slow intravenous injection, however, produces none of these effects. Thaliblastine is cytotoxic to HEF and Sa9 cells in vitro.

Technology Process of Thalicarpine

There total 4 articles about Thalicarpine 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: 74.0%

C47H56N2O12 + methyl iodide (74-88-4) → Thalicarpine (4829-32-7,16624-97-8,35721-25-6,5373-42-2)

Guidance literature:

C₄₇H₅₆N₂O₁₂; methyl iodide; With caesium carbonate; In dimethyl sulfoxide;

With lithium aluminium tetrahydride; In tetrahydrofuran; for 12h; Reflux;

DOI:10.1021/acscatal.8b04443

Reference yield:

→ Thalicarpine (4829-32-7,16624-97-8,35721-25-6,5373-42-2)

Guidance literature:

N-Methyl-laurotetanin, L-6'-Brom-laudanosin, CuO, wfr. K2CO3, wfr. Py., 140-145grad;

Reference yield:

→ Thalicarpin (4829-32-7,5373-42-2,16624-97-8,35721-25-6)

Guidance literature:

12 1.)Zn 2.)HCOH, HCOOH;

DOI:10.1021/ja00790a044

upstream raw materials:

methyl iodide

Refernces

• 1、 -. "Compounds and compositions for treating infection". . . Retrieved 2009/04/24.
• 2、 Kupchan,Liepa,Kameswaran,Sempuku. "Total synthesis of the tumor-inhibitory alkaloid thalicarpine.". . p. 2995 - 3000. Retrieved 2007/10/04.