Isoginkgetin

Base Information

• Chemical Name: Isoginkgetin
• CAS No.: 548-19-6
• Molecular Formula: C32H22 O10
• Molecular Weight: 566.521
• DSSTox Substance ID: DTXSID00203271
• Nikkaji Number: J11.548G
• Wikidata: Q27148149
• Metabolomics Workbench ID: 46293
• ChEMBL ID: CHEMBL1208903
• Mol file: 548-19-6.mol

Synonyms:iso-ginkgetin;isoginkgetin

Chemical Property of Isoginkgetin

Chemical Property:

• Vapor Pressure: 8.5E-30mmHg at 25°C
• Melting Point: 355oC
• Boiling Point: 843.6°Cat760mmHg
• PKA: 6.16±0.40(Predicted)
• Flash Point: 280.2°C
• PSA: 159.80000
• Density: 1.506g/cm³
• LogP: 5.74000
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 566.12129689
• Heavy Atom Count: 42
• Complexity: 1080

Purity/Quality:

99% ^*data from raw suppliers

Isoginkgetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)OC
• Description: Isoginkgetin is a biflavonoid that has been found in G. biloba and is an inhibitor of pre-mRNA splicing. Isoginkgetin (33 μM) reduces the activity of an mRNA-dependent luciferase reporter by 5-fold, shifts the composition of total RNA extract from predominantly mRNA to pre-mRNA, and arrests cell growth in HEK293 cells. Isoginkgetin (10 μM) suppresses mouse lymphocyte proliferation induced by concanavalin A (Con A; ) and LPS by approximately 87 and 90%, respectively. It also suppresses arachidonic acid release induced by phorbol 12-myristate 13-acetate (PMA; ) and the calcium ionophore A23187 by 32.5 and 48.4%, respectively, in rat peritoneal macrophages when used at a concentration of 10 μM. Isoginkgetin (5-20 μM) reduces matrix metalloproteinase-9 (MMP-9) activity, expression, and mRNA levels in and decreases cell invasion by HT1080 fibrosarcoma cells in a concentration-dependent manner.

Technology Process of Isoginkgetin

There total 8 articles about Isoginkgetin 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:

(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(3-iodo-4-methoxyphenyl)prop-2-en-1-one → isoginkgetin (548-19-6)

Guidance literature:

Multi-step reaction with 4 steps

1: iodine / dimethyl sulfoxide / 16 h / 100 °C / Inert atmosphere

2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere; Sealed tube

3: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation

4: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C

With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; tetrakis-(triphenylphosphine)-palladium; palladium 10% on activated carbon; palladium hydroxide on carbon; hydrogen; iodine; anhydrous potassium acetate; sodium hydroxide; In methanol; dichloromethane; water monomer; dimethyl sulfoxide; N,N-dimethyl-formamide; 2: |Miyaura Borylation Reaction / 3: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.1c01654

Reference yield:

5,7-bis(benzyloxy)-8-iodo-2-(4-methoxyphenyl)-4H-chromen-4-one → isoginkgetin (548-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation

2: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C

With tetrakis-(triphenylphosphine)-palladium; palladium 10% on activated carbon; palladium hydroxide on carbon; hydrogen; sodium hydroxide; In methanol; dichloromethane; water monomer; N,N-dimethyl-formamide; 1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.1c01654

Reference yield:

5,7-bis(benzyloxy)-2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4H-chromen-4-one → isoginkgetin (548-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide; tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide; water monomer / 80 °C / Inert atmosphere; Sealed tube; Microwave irradiation

2: palladium 10% on activated carbon; hydrogen; palladium hydroxide on carbon / dichloromethane; methanol / 5 h / 20 °C

With tetrakis-(triphenylphosphine)-palladium; palladium 10% on activated carbon; palladium hydroxide on carbon; hydrogen; sodium hydroxide; In methanol; dichloromethane; water monomer; N,N-dimethyl-formamide; 1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.1c01654

upstream raw materials:

3,5-dihydroxyphenol

ethyl 4-methoxybenzoylacetate

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

Downstream raw materials:

4-methoxyisophthalic acid

4-methoxybenzoic acid

amentoflavone

Amentoflavon

Refernces