182572-57-2

Basic information

• Product Name: (E)-4-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid
• Synonyms: (E)-4-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid
• CAS NO: 182572-57-2
• Molecular Weight: 294.304
• Mol File: 182572-57-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-4-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid(182572-57-2)
• EPA Substance Registry System: (E)-4-(3,4-dimethoxyphenyl)-3-(ethoxycarbonyl)but-3-enoic acid(182572-57-2)

Safety Data

• Hazardous Substances Data: 182572-57-2(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 123-25-1 succinic acid diethyl ester 

Downstream Products

• 58402-11-2 (E)-diethyl 2-(3,4-dimethoxybenzylidene)succinate 

Relevant articles and documents

Total synthesis of leoligin from edelweiss roots

Leoligin, a tetrahydrofuran lignan isolated from the root of the edelweiss plant, was synthesised from veratraldehyde (2 mol), diethyl succinate and 2-methyl-(Z)-2-butenoic acid. Initially, veratraldehyde and diethyl succinate underwent a Stobbe condensation to yield a C6-C5 acid which, after esterification, was condensed with a second molecule of veratraldehyde to generate a 2,3,4-trisubsituted γ-butyrolactone intermediate. Two reduction steps yielded a triol, which was ring-closed with tosyl chloride to form a hydroxymethyl-tetrahydrofuran, esterification of which with 2-methyl-(Z)-2-butenoic acid generated leoligin.

Antiproliferative and apoptotic effects of the oxidative dimerization product of methyl caffeate on human breast cancer cells

Caffeic acid derivatives are increasingly regarded as potential oncoprotective that could inhibit both the initiation and progression of cancer. Here we have synthesized seven 1-arylnaphthalene lignans and related compounds and tested their impact on breast cancer cell growth in tissue culture. The product of the oxidative dimerization of methyl caffeate, 1-phenylnaphthalene lignan, was found to induce a strong decrease in breast cancer cell number (IC50 ～1 μM) and was selected for further investigation. Flow cytometry analysis revealed a decrease in cell proliferation and an increase in apoptosis in both MCF-7 and MDA-MB-231 breast cancer cell lines that are representative of the two main categories of breast tumors. The 3,4-dihydroxyphenyl group probably induced the biological activity, as the control compounds lacking it had no effect on breast cancer cells. Together, our data indicate that the oxidative dimerization product of methyl caffeate can inhibit breast cancer cell growth at a concentration adequate for pharmacological use.