Bufotalin

Base Information

• Chemical Name: Bufotalin
• CAS No.: 471-95-4
• Molecular Formula: C26H36 O6
• Molecular Weight: 444.568
• Hs Code.: 29329990
• UNII: EGL9670I6P
• ChEMBL ID: CHEMBL463064
• DSSTox Substance ID: DTXSID60894008
• Metabolomics Workbench ID: 121110
• Nikkaji Number: J5.948J
• Wikidata: Q5760807
• Wikipedia: Bufotalin
• Mol file: 471-95-4.mol

Synonyms:bufotalin

Chemical Property of Bufotalin

Chemical Property:

• Appearance/Colour: White to off-white solid.
• Vapor Pressure: 1.82E-16mmHg at 25°C
• Melting Point: 223°C (rough estimate)
• Refractive Index: 1.4593 (estimate)
• Boiling Point: 591.7 °C at 760 mmHg
• PKA: 14.44±0.70(Predicted)
• Flash Point: 195.8 °C
• PSA: 96.97000
• Density: 1.26 g/cm³
• LogP: 3.78350
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 444.25118886
• Heavy Atom Count: 32
• Complexity: 878

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bufotalin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC2(C3CCC4CC(CCC4(C3CCC2(C1C5=COC(=O)C=C5)C)C)O)O
• Isomeric SMILES: CC(=O)O[C@H]1C[C@@]2([C@@H]3CC[C@@H]4C[C@H](CC[C@@]4([C@H]3CC[C@@]2([C@H]1C5=COC(=O)C=C5)C)C)O)O
• Uses: Bufotalin is a component of Bufo bufo gargarizans which acts as an anti-tumor agent.

Technology Process of Bufotalin

There total 2 articles about Bufotalin 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:

bufotalin 3-pimeloylarginine ester (1337864-09-1) → heptanedioic acid (111-16-0) + L-arginine (74-79-3,25212-18-4) + bufotalin (471-95-4)

Guidance literature:

With hydrogenchloride; water; In 1,4-dioxane; at 80 ℃; for 4h;

DOI:10.1080/10286020.2010.505187

Reference yield:

Epietiocholanolone (571-31-3) → bufotalin (471-95-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 70 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: palladium diacetate / dichloromethane; acetonitrile / 25 h / 20 °C / Inert atmosphere

4.1: silica gel; N-ethyl-N,N-diisopropylamine / 4 h / 80 °C / Inert atmosphere

5.1: oxygen; phenylsilane; cobalt(II) aceylacetonate / 1,4-dioxane / 5 h / 20 °C / 760.05 Torr

6.1: triethylamine; hydrazine hydrate / ethanol / 13 h / 50 °C / Inert atmosphere

6.2: 0.67 h / 0 °C

7.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) chloride; lithium chloride / dimethyl sulfoxide; tetrahydrofuran / 13 h / 60 °C / Inert atmosphere

8.1: 3-chloro-benzenecarboperoxoic acid; sodium carbonate / dichloromethane / 5 h / -78 - -20 °C / Inert atmosphere

9.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

10.1: methanol; sodium tetrahydroborate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

11.1: pyridine / 18 h / 20 °C / Inert atmosphere

12.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 124 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; phenylsilane; oxygen; palladium diacetate; silica gel; sodium carbonate; pyridine hydrogenfluoride; cobalt(II) aceylacetonate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; lithium chloride; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.orglett.0c03251

Reference yield:

bufotalin (471-95-4) → 5?[(3S,5R,8R,9S,10S,13S)?3?hydroxy?10,13?di?methyl?2,3,4,5,6,7,8,9,10,11,12,13?dodecahydro?1H?cyclopenta[a]phenanthren?17?yl]?2H?pyran?2?one (474-53-3)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

bufotalin 3-pimeloylarginine ester

Epietiocholanolone

Downstream raw materials:

5?[(3S,5R,8R,9S,10S,13S)?3?hydroxy?10,13?di?methyl?2,3,4,5,6,7,8,9,10,11,12,13?dodecahydro?1H?cyclopenta[a]phenanthren?17?yl]?2H?pyran?2?one

Refernces

• 1、 Zhao, Hu-Yi,Wu, Fu-Kai,Qiu, Ying-Kun,Wu, Zhen,Jiang, Yong-Tao,Chen, Ji-Yong. "Studies on cytotoxic constituents from the skin of the toad Bufo bufo gargarizans". experimental part. p. 793 - 800. Retrieved 2010/12/20.