23666-13-9

Basic information

• Product Name: VICENIN
• Synonyms: 2-(4-Hydroxyphenyl)-5,7-dihydroxy-6,8-bis(β-D-glucopyranosyl)-4H-1-benzopyran-4-one;6,8-Di(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;Apigenin 6,8-C-diglucoside;5,7-Dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one;Vicenin-2;Vicenin-II;4H-1-Benzopyran-4-one,6,8-di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-;6,8-Di-C-β-D-glucopyranosylapigenin
• CAS NO: 23666-13-9
• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.519
• Mol File: 23666-13-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: >250 °C (decomp)
• Boiling Point: 974.7ºC at 760 mmHg
• Flash Point: 323.7ºC
• Appearance: /
• Density: 1.758g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.748
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly, Heated, Sonicated), DMSO (Slightly)
• PKA: 5.68±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: VICENIN(CAS DataBase Reference)
• NIST Chemistry Reference: VICENIN(23666-13-9)
• EPA Substance Registry System: VICENIN(23666-13-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23666-13-9(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2

Upstream product

• 82616-06-6 5,7,4'-triacetoxy-6,8-di-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)flavone 
• 1646598-05-1 apigenin-6-C-β-D-glucopyranosyl-8-C-[β-D-apiofuranosyl-(1→2)]-β-D-glucopyranoside 
• 1646598-06-2 apigenin-6-C-β-D-glucopyranosyl-8-C-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside 

Downstream Products

• 82616-06-6 5,7,4'-triacetoxy-6,8-di-C-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)flavone 

Relevant articles and documents

Total Synthesis of (+)-Vicenin-2

The bis-C-glucosyl flavonoid vicenin-2 (1) has been synthesized by exploiting bis-C-glycosylation of 1,3,5-trifluorobenzene and aromatic nucleophilic substitution to transform fluorine atoms to oxygen functions in excellent yield.

New flavone-di-C-glycosides from the seeds of Egyptian lupin (Lupinus termis)

Raw lupin seeds flour is increasingly used as a food ingredient because of its nutritional and functional values. This study is considered to be the first phytochemical investigation of the flavonoids of the methanol (MeOH) fraction of Lupinus termis seeds. The study led to the isolation of two new di-C-glycoside flavones, apigenin-6-C-β-d-glucopyranosyl-8-C-[β-d-apiofuranosyl-(1 → 2)]-β-glucopyranoside (1), apigenin-6-C-β-d-glucopyranosyl-8-C- [α-l-rhamnopyranosyl-(1 → 2)]-β-glucopyranoside (2), together with one known flavone di-C-glycoside, apigenin-7-O-β-d-apiofuranosyl-6,8- di-C-β-glucopyranoside (3). These compounds are considered to have potential functional properties. The isolated compounds may contribute to the yellow color of raw lupin seeds flour-based products. It may also be used as natural yellow color in food or pharmaceutical products and as a dietary supplement product. These rare flavones were purified by using semi-preparative HPLC. The structures of the isolated compounds were elucidated on the basis of extensive spectroscopic methods, 1D and 2D nuclear magnetic resonance techniques, FAB (Fast Atom Bombardment) - mass spectrometry and acid hydrolysis.

Unusual phenolic glycosides from Cotoneaster orbicularis

The whole plant of Cotoneaster orbicularis contains the novel di-C- glycosylflavone, 4'',4'''-di-O-β-glucopyranosyl-vicenin II, or 6,8-di-C-β- Cellobiosylapigenin, as well as the hitherto unknown natural phenolic glucoside, gentisic acid 2-O-β-glucopyranoside, or orbicularin. Further phenolics are protocatechuic, anisic, caffeic, p-coumaric acids, catechin, epicatechin, 2''-O-α-rhamnopyranosylvitexin, vitexin, rutin, isoquercetrin, hyperin and naringenin. All structures were determined by routine methods of analysis and confirmed mostly by 1H- and 13C-NMR. (C) 2000 Elsevier Science Ltd.