2,3-Dehydrosilybin A

Base Information

• Chemical Name: 2,3-Dehydrosilybin A
• CAS No.: 25166-14-7
• Deprecated CAS: 25166-13-6,26950-33-4,56833-34-2
• Molecular Formula: C₂₅H₂₀O₁₀
• Molecular Weight: 480.428
• DSSTox Substance ID: DTXSID60858706
• Nikkaji Number: J533.197H
• Wikidata: Q81977802
• Metabolomics Workbench ID: 144240
• ChEMBL ID: CHEMBL315670
• Mol file: 25166-14-7.mol

Synonyms:2,3-Dehydrosilybin A;2,3-Dehydrosilybin A;CHEMBL315670;DTXSID60858706;AKOS040735208

Chemical Property of 2,3-Dehydrosilybin A

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 480.10564683
• Heavy Atom Count: 35
• Complexity: 816

Purity/Quality:

HPLC≥95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
• Isomeric SMILES: COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3)C4=C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O

Technology Process of 2,3-Dehydrosilybin A

There total 4 articles about 2,3-Dehydrosilybin A 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: 91.0%

silibinin (22888-70-6) → 3-hydroxyhydnocarpin-D (25166-14-7)

Guidance literature:

With pyridine; iodine; magnesium chloride; at 100 ℃; for 1h; Temperature; Reagent/catalyst; Time;

DOI:10.1016/j.tetlet.2018.03.052

Reference yield: 75.0%

silibinin (22888-70-6) → 3-hydroxyhydnocarpin-D (25166-14-7) + 19-O-demethyl-2,3-dehydrosilybin

Guidance literature:

With pyridine; aluminum (III) chloride; iodine; at 110 ℃; for 1h;

DOI:10.1016/j.tetlet.2018.03.052

Reference yield: 69.0%

→ 3-hydroxyhydnocarpin-D (25166-14-7)

Guidance literature:

With pyridine; iodine; at 10 ℃; for 0.5h; under 760.051 Torr;

at 170 ℃; for 0.045h; under 7500.75 Torr;

upstream raw materials:

silibinin

silybin

Refernces

• 1、 Wen, Yong-ju,Zhou, Zong-yuan,Zhang, Guo-lin,Lu, Xiao-xia. "Metal coordination protocol for the synthesis of-2,3-dehydrosilybin and 19-O-demethyl-2,3-dehydrosilybin from silybin and their antitumor activities". . p. 1666 - 1669. Retrieved 2018.
• 2、 Sciacca, Michele. F. M.,Romanucci, Valeria,Zarrelli, Armando,Monaco, Irene,Lolicato, Fabio,Spinella, Natalia,Galati, Clelia,Grasso, Giuseppe,D'Urso, Luisa,Romeo, Margherita,Diomede, Luisa,Salmona, Mario,Bongiorno, Corrado,Di Fabio, Giovanni,La Rosa, Carmelo,Milardi, Danilo. "Inhibition of Aβ Amyloid Growth and Toxicity by Silybins: The Crucial Role of Stereochemistry". . p. 1767 - 1778. Retrieved 2017/08/21.