Thalrugosine

Base Information

• Chemical Name: Thalrugosine
• CAS No.: 33889-68-8
• Deprecated CAS: 39347-58-5
• Molecular Formula: C₃₇H₄₀N₂O₆
• Molecular Weight: 608.734
• UNII: 863BR78K9R
• Nikkaji Number: J17.831D
• Wikipedia: Fangchinoline
• Wikidata: Q104402141
• Metabolomics Workbench ID: 139562
• ChEMBL ID: CHEMBL500614
• Mol file: 33889-68-8.mol

Synonyms:(1beta)-isomer of fangchinoline;7-O-demethyl-tetrandrine;7-O-demethyltetrandrine;berbaman-7-ol, 6,6',12-trimethoxy-2,2'-dimethyl-, (1beta)-;fangchinoline;isofangchinoline;limacine;thaligine;thalrugosine

Chemical Property of Thalrugosine

Chemical Property:

• Vapor Pressure: 8.25E-21mmHg at 25°C
• Refractive Index: 1.601
• Boiling Point: 709.7 °C at 760 mmHg
• PKA: 9.38±0.20(Predicted)
• Flash Point: 383 °C
• PSA: 72.86000
• Density: 1.204 g/cm³
• LogP: 6.73520
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly), Methanol (Sl
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 608.28863700
• Heavy Atom Count: 45
• Complexity: 963

Purity/Quality:

98%, ^*data from raw suppliers

Fangchinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@@H]6C7=C(O3)C(=C(C=C7CCN6C)OC)O)OC)OC
• Uses: Fangchinoline is an isolate from Stephania Tetrandra that shows anti-cancer activity. It inhibits breast adenocarcinoma proliferation through apoptosis induction. In addition, it has been shown to inhibit HIV-Type 1 replication.
• Description: Thalictrum rugosum Ait also contains this alkaloid which is dextrorotatory with [o:lbo + 128° (MeOH). The ultraviolet spectrum of this base consists of a single absorption maximum at 283 flI/J..

Technology Process of Thalrugosine

There total 8 articles about Thalrugosine 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: 51.5%

Tetrandrin (518-34-3,5990-67-0) → fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9)

Guidance literature:

With hydrogen bromide; acetic acid; at 90 ℃; for 8h;

DOI:10.1016/j.bioorg.2021.104694

Reference yield: 35.0%

Tetrandrin (518-34-3,5990-67-0) → Atherospermoline (21008-67-3) + (+)-penduline (26137-45-1) + 6',7-Bis-(O-demethyl)-tetrandrine (83087-72-3) + fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9)

Guidance literature:

With hydrogen bromide; at 20 ℃; for 24h; Yield given. Further byproducts given;

DOI:10.1002/ardp.19823150705

Reference yield: 35.0%

Tetrandrin (518-34-3,5990-67-0) → Tetrakis-(O-demethyl)-tetrandrin (83113-25-1) + Atherospermoline (21008-67-3) + (+)-penduline (26137-45-1) + 6',7,12-Tris-(O-demethyl)-tetrandrine (83113-24-0) + 6',7-Bis-(O-demethyl)-tetrandrine (83087-72-3) + fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9)

Guidance literature:

With hydrogen bromide; at 20 ℃; for 24h; Product distribution; different concentration of HBr, different times and temperatures;

DOI:10.1002/ardp.19823150705

upstream raw materials:

Tetrandrin

(+)-isotetrandrine

Downstream raw materials:

(+)-isotetrandrine

7-isopropoxy fangchinoline

Refernces

• 1、 Li, Jiayuan,Li, Li,Li, Xuyu,Liu, Yanfei,Shi, Guoru,Wang, Renzhong,Yu, Dequan,Yuan, Jiqiao,Zhou, Jie. "Bioactive bisbenzylisoquinoline alkaloids from the roots of Stephania tetrandra". . . Retrieved 2020/03/17.
• 2、 Pachaly,Praest. "Phenolic derivatives from the bisbenzylisoquinoline alkaloid tetrandrine by selective ether cleavage". . p. 589 - 597. Retrieved 2007/10/02.