521-34-6

Basic information

• Product Name: SCIADOPITYSIN
• Synonyms: AMENTOFLAVONE-7,4',4'''-TRIMETHYL ETHER;AMENTOFLAVONE-7,4',4''-TRIMETHYL ETHER;AMENTOFLAVONE-7,4',4'-TRIMETHYL ETHER;SCIADOPITYSIN;5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-methoxyphenyl)-4-benzopyrone;SCIADOPITYSIN(SH);AMENTOFLAVONE-7,4'',4''-TRIMETHYL ETHER WITH HPLC;2-(4-Methoxyphenyl)-5,7-dihydroxy-8-[2-methoxy-5-(4-oxo-5-hydroxy-7-methoxy-4H-1-benzopyran-2-yl)phenyl]-4H-1-benzopyran-4-one
• CAS NO: 521-34-6
• Molecular Formula: C₃₃H₂₄O₁₀
• Molecular Weight: 580.54
• EINECS: 208-311-5
• Product Categories: Tri-substituted Flavones
• Mol File: 521-34-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 296-298°C
• Boiling Point: 839.6 °C at 760 mmHg
• Flash Point: 276.2 °C
• Appearance: /
• Density: 1.445 g/cm³
• Vapor Pressure: 1.7E-29mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: 2-8°C
• PKA: 6.16±0.40(Predicted)
• CAS DataBase Reference: SCIADOPITYSIN(CAS DataBase Reference)
• NIST Chemistry Reference: SCIADOPITYSIN(521-34-6)
• EPA Substance Registry System: SCIADOPITYSIN(521-34-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 521-34-6(Hazardous Substances Data)

Usage

Description

Sciadopitysin is a biflavonoid originally isolated from G. biloba and has diverse biological activities. It reduces cytotoxicity induced by amyloid-β (1-42) (Aβ42; ) in PC12 cells (EC50 = 9.84 μM). Sciadopitysin (0.1-10 μM) decreases methylglyoxal-induced insulin secretion, production of reactive oxygen species (ROS), cardiolipin peroxidation, and cytotoxicity in RIN-m5F pancreatic β-cells. It inhibits P-glycoprotein (P-gp; IC50 = 53.42 μM) and increases cellular toxicity of paraquat and paclitaxel in MDR1-MDCKII cells. Sciadopitysin inhibits RANKL-induced mRNA expression of the osteoclast-specific genes CTSK, TRAP, and MMP-9, activation of NF-κB, and osteoclastogenesis in a mouse model of LPS-induced bone loss.

Definition

ChEBI: A biflavonoid that is a 7, 4', 4'''-trimethyl ether derivative of amentoflavone.

InChI:InChI=1/C33H24O10/c1-39-18-7-4-16(5-8-18)27-15-25(38)32-23(36)13-22(35)30(33(32)43-27)20-10-17(6-9-26(20)41-3)28-14-24(37)31-21(34)11-19(40-2)12-29(31)42-28/h4-15,34-36H,1-3H3

Upstream product

• 3754-52-7 3'-iodo-5,7,4'-trimethoxyflavone 
• 135159-01-2 C₂₂H₂₅BO₇ 
• 135197-04-5 8-[5-(5,7-Dimethoxy-4-oxo-4H-chromen-2-yl)-2-methoxy-phenyl]-5,7-diisopropoxy-2-(4-methoxy-phenyl)-chromen-4-one 

Downstream Products

• 7507-89-3 2,6-dihydroxy-4-methoxy-acetophenone 
• 95803-60-4 8-(5-acetyl-2-methoxy-phenyl)-5,7-dihydroxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 438051-00-4 3-[5,7-dihydroxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-8-yl]-4-methoxybenzoic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 17482-35-8 sciadopitysin triacetate 

Relevant articles and documents

A new strategy for the synthesis of biflavonoids via arylboronic acids

Amentoflavone derivatives were prepared by catalytic coupling of 8-flavone-boronic acids with iodoflavones. 3-Arylflavones, as biflavonoid synthon, are accessible by the method.