Erysotrine

Base Information

• Chemical Name: Erysotrine
• CAS No.: 27740-43-8
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.397
• DSSTox Substance ID: DTXSID80182090
• Nikkaji Number: J404.521A
• Wikidata: Q27106501
• Metabolomics Workbench ID: 44286
• ChEMBL ID: CHEMBL442947
• Mol file: 27740-43-8.mol

Synonyms:Erysotrine;27740-43-8;(+)-Erysotrine;CHEBI:4838;(2R,13bS)-2,11,12-trimethoxy-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinoline;Erythrinan, 1,2,6,7-tetradehydro-3,15,16-trimethoxy-, (3beta)-;C09423;CHEMBL442947;DTXSID80182090;HY-N3852;BDBM50006648;AKOS032948694;CS-0024334;Q27106501;(1S,16R)-4,5,16-trimethoxy-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2(7),3,5,12,14-pentaene

Chemical Property of Erysotrine

Chemical Property:

• Vapor Pressure: 3.81E-09mmHg at 25°C
• Boiling Point: 473.8°Cat760mmHg
• Flash Point: 141.2°C
• PSA: 30.93000
• Density: 1.21g/cm³
• LogP: 2.61000
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 313.16779360
• Heavy Atom Count: 23
• Complexity: 517

Purity/Quality:

98%min ^*data from raw suppliers

Erysotrine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1CC23C(=CCN2CCC4=CC(=C(C=C34)OC)OC)C=C1
• Isomeric SMILES: CO[C@@H]1C[C@@]23C(=CCN2CCC4=CC(=C(C=C34)OC)OC)C=C1
• Uses: Erysotrin is an alkaloid found in the flowers and pods of Erythrina lysistemon, analyzed in studies for its DPPH radical scavenging properties.

Technology Process of Erysotrine

There total 64 articles about Erysotrine 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: 94.0%

(+)-erysotramidine (52358-58-4) → erysotrine (27740-43-8,70635-23-3,70635-25-5,70681-68-4)

Guidance literature:

With lithium aluminium tetrahydride; aluminium trichloride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.666667h;

DOI:10.3987/COM-91-S65 DOI:10.1248/cpb.41.2087

Reference yield: 80.0%

(+/-)-3α,15,16-trimethoxy-8-oxo-Δ1,6-erythrinan (52358-58-4,69111-35-9,112342-35-5) → (+/-)-erysotrine (27740-43-8,70635-23-3,70635-25-5,70681-68-4)

Guidance literature:

With aluminium hydride; In tetrahydrofuran; for 0.75h;

DOI:10.1248/cpb.35.479

Reference yield: 80.0%

(+/-)-Oxoerythratidine → (+/-)-erysotrine (27740-43-8,70635-23-3,70635-25-5,70681-68-4) + (+/-)-Erythratidine

Guidance literature:

With aluminium hydride; In diethyl ether; dimethyl sulfoxide; at 0 ℃; for 3.5h;

DOI:10.1039/b001906m

upstream raw materials:

(+)-erysotramidine

(+)-11β-acetoxyerysotramidine

diazomethane

(5R)-(+)-15,16-dimethoxy-3,8-dioxoeryhtrinan-1,6-diene

Downstream raw materials:

erythristemine

Refernces

• 1、 Hosoi, Shinzo,Nagao, Motoyoshi,Tsuda, Yoshisuke,Isobe, Kimiaki,Sano, Takehiro,Ohta, Tomihisa. "Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxy-erythrinans: Total synthesis of an alkenoid-type erythrinan alkaloid, (±)-erythratidine". . p. 1505 - 1511. Retrieved 2007/10/03.
• 2、 Tsuda,Hosoi,Katagiri,Kaneko,Sano. "Chiral synthesis of Erythrina alkaloids. I. Total synthesis of (+)-erysotrine via asymmetric Diels-Alder reaction under high pressure". . p. 2087 - 2095. Retrieved 2007/10/02.