Vicenin-2

Base Information

• Chemical Name: Vicenin-2
• CAS No.: 23666-13-9
• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.526
• Wikidata: Q104387517
• Mol file: 23666-13-9.mol

Synonyms:apigenin-6,8-di-C-glycopyranoside;vicenin II;vicenin-2

Chemical Property of Vicenin-2

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >250 °C (decomp)
• Boiling Point: 974.7ºC at 760 mmHg
• PKA: 5.68±0.40(Predicted)
• Flash Point: 323.7ºC
• PSA: 271.20000
• Density: 1.758g/cm3
• LogP: -2.39340
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly, Heated, Sonicated), DMSO (Slightly)
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 5
• Exact Mass: 594.15847025
• Heavy Atom Count: 42
• Complexity: 987

Purity/Quality:

99.5% ^*data from raw suppliers

Vicenin-II ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O
• Uses: Vicenin 2 (CAS# 23666-13-9) is a biologically active compound extracted from Hypericum salsugineum and displays significant anti-cancer effects on breast carcinoma cell lines.

Technology Process of Vicenin-2

There total 8 articles about Vicenin-2 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: 92.0%

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-6,8-bis((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one → vicenin-2 (19335-29-6,23666-13-9,82043-11-6,90898-93-4,61393-93-9)

Guidance literature:

With 10% palladium hydroxide on charcoal; water; hydrogen; In ethanol; ethyl acetate; at 20 ℃; for 12h;

DOI:10.1021/acs.orglett.6b02203

Reference yield: 90.7%

5,7,4'-triacetoxy-6,8-di-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)flavone (82616-06-6) → vicenin-2 (19335-29-6,23666-13-9,82043-11-6,90898-93-4,61393-93-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2006.02.019

Reference yield:

2'',2'''-di-O-α-rhamnopyranosyl vicenin II → vicenin-2 (19335-29-6,23666-13-9,82043-11-6,90898-93-4,61393-93-9) + L-Rhamnose (3615-41-6,478518-52-4)

Guidance literature:

With hydrogenchloride; In methanol; water; at 100 ℃; for 7h;

DOI:10.1691/ph.2016.5821

upstream raw materials:

5,7,4'-triacetoxy-6,8-di-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)flavone

apigenin-6-C-β-D-glucopyranosyl-8-C-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside

apigenin-6-C-β-D-glucopyranosyl-8-C-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside

Downstream raw materials:

5,7,4'-triacetoxy-6,8-di-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)flavone

Refernces

• 1、 Ho, Thanh C.,Kamimura, Haruki,Ohmori, Ken,Suzuki, Keisuke. "Total Synthesis of (+)-Vicenin-2". supporting information. p. 4488 - 4490. Retrieved 2016/09/28.
• 2、 Sato, Shingo,Akiya, Toshiki,Nishizawa, Hiroaki,Suzuki, Toshiyuki. "Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-d-glucosides". . p. 964 - 970. Retrieved 2007/10/03.