Isoscoparin

Base Information

• Chemical Name: Isoscoparin
• CAS No.: 20013-23-4
• Molecular Formula: C22H22O11
• Molecular Weight: 462.41
• DSSTox Substance ID: DTXSID70941996
• Nikkaji Number: J338.086F
• Wikidata: Q27102895
• Metabolomics Workbench ID: 51190
• Mol file: 20013-23-4.mol

Synonyms:Isoscoparin;20013-23-4;C-Glucosyl-6 chrysoeriol;Chrysoeriol 6-C-glucoside;Isoscoparine;5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one;5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one;(1S)-1,5-anhydro-1-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-6-yl]-D-glucitol;C05990;Kaempherol 3-O-beta-sophoroside;CHEBI:18200;DTXSID70941996;HY-N5080;AKOS040760486;CS-0032312;D85179;Q27102895;1,5-Anhydro-1-[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-6-yl]hexitol

Chemical Property of Isoscoparin

Chemical Property:

• Vapor Pressure: 2.39E-28mmHg at 25°C
• Boiling Point: 818.6°Cat760mmHg
• PKA: 5.90±0.40(Predicted)
• Flash Point: 287°C
• PSA: 190.28000
• Density: 1.649g/cm³
• LogP: 0.10030
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 462.11621151
• Heavy Atom Count: 33
• Complexity: 744

Purity/Quality:

≥98% ^*data from raw suppliers

Isoscoparin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)C4C(C(C(C(O4)CO)O)O)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O

Technology Process of Isoscoparin

There total 5 articles about Isoscoparin 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: 53.0%

C16H14O7 + UDP-glucose → 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-β-D-glucopyranoside (20013-23-4) + chrysoeriol 8-C-glucoside (301-16-6)

Guidance literature:

With recombinant Oryza sativa C-glycosyltransferase; In ethanol; at 30 ℃; pH=7.5; Enzymatic reaction;

DOI:10.1016/j.phytochem.2016.02.013

Reference yield:

isoscoparin-2''-β-D-glucopyranoside (97605-25-9) → 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-β-D-glucopyranoside (20013-23-4)

Guidance literature:

With hydrogenchloride; In methanol; water; at 100 ℃; for 4h;

DOI:10.1016/j.phytochem.2020.112312

Reference yield:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone (18065-05-9) → 3'-methoxy-5,7,4'-trihydroxyflavone 6-C-β-D-glucopyranoside (20013-23-4) + chrysoeriol 8-C-glucoside (301-16-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / Reflux

2: potassium hydroxide / pyridine / 1 h / 85 °C / Inert atmosphere

3: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran

4: recombinant Oryza sativa C-glycosyltransferase / ethanol / 30 °C / pH 7.5 / Enzymatic reaction

With dmap; palladium 10% on activated carbon; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; 2: |Baker-Venkataraman Rearrangement;

DOI:10.1016/j.phytochem.2016.02.013

upstream raw materials:

1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

isoscoparin-2''-β-D-glucopyranoside

Refernces

• 1、 Hao,Caulfield,Hamilton,Pickett,Midega,Khan,Wang,Hooper. "Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins". . p. 73 - 87. Retrieved 2016/04/06.