69232-85-5

Basic information

• Product Name: 4-(3,4-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one
• Synonyms: 4-(3,4-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one
• CAS NO: 69232-85-5
• Molecular Weight: 414.455
• Mol File: 69232-85-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-(3,4-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,4-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one(69232-85-5)
• EPA Substance Registry System: 4-(3,4-dimethoxybenzyl)-3-(4'-acetoxy-3'-methoxybenzyl)dihydrofuran-2(3H)-one(69232-85-5)

Safety Data

• Hazardous Substances Data: 69232-85-5(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 26687-82-1 Arctigenin 
• 75-36-5 acetyl chloride 

Downstream Products

• 80287-36-1 α-conidendrin monomethyl ether 
• 74861-36-2 5-acetoxyarctigenin monoacetate 
• 69610-59-9 5-allohydroxymatairesinol dimethyl ether 
• 74861-41-9 5-alloacetoxymatairesinol dimethyl ether 
• 74861-40-8 (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone 
• 71772-18-4 α-conidendrin dimethyl ether 

Relevant articles and documents

Studies on differentiation inducers. VI. Lignan derivatives from arctium fructus. (2)

In the previous paper, we reported the differentiation inducing activities of lignoids from Arctium Fructus (the fruits of Arctium lappa L., Compositae) against mouse myeloid leukemia cells (M1). We reinvestigated the active components of this extract and isolated three new dilignans. Furthermore, structure modifications were carried out using the most active lignan (arctigenin, 1) and its structure activity relationship was investigated. Its aliphatic esters were more effective in inducing the differentiation of M1 cells than its aromatic esters. Especially, n- decanoate, which was the most active derivative, induced more than half of the M1 cells into phagocytic cells at a concentration of 2 μM.

Synthesis and anticancer evaluation of (-)-arctigenin derivatives

Seven (-)-arctigenin derivatives 1-7 were designed and synthesized by using Mannich and acylation methods to improve the activity and bioavailability of (-)-arctigenin. Structures of compounds 1-7 were elucidated on the basis of spectroscopic analysis and chemical evidence. Anticancer activity of these compounds on SGC7901 was assayed in vitro.

Studies on differentiation-inducers from Arctium Fructus

In the course of studying differentiation-inducers from plants, their isolation was performed from the methanolic extract of Arctium Fructus (the fruits of Arctium lappa L., Compositae), and then their phagocytic activity on differentiated mouse myeloid leukemia cells (MI) was monitored. Thirteen compounds, including five new ones, were isolated as differentiation-inducers toward MI cells. These consisted of two lignans, eight sesquilignans and three dilignans. Arctigenin (2) was the most effective compound of all those isolated, and it induced differentiation of MI cells at a concentration 0.5 μM. Sesquilignans were less effective than lignans and dilignans showed even weaker activity. These lignoids were inactive towards a human acute promyelocytic leukemia cell line (HL-60).