88909-07-3

Basic information

• Product Name: (E)-3-(3,4-dimethoxyphenyl)acrylic anhydride
• Synonyms: (E)-3-(3,4-dimethoxyphenyl)acrylic anhydride
• CAS NO: 88909-07-3
• Molecular Weight: 398.412
• Mol File: 88909-07-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (E)-3-(3,4-dimethoxyphenyl)acrylic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(3,4-dimethoxyphenyl)acrylic anhydride(88909-07-3)
• EPA Substance Registry System: (E)-3-(3,4-dimethoxyphenyl)acrylic anhydride(88909-07-3)

Safety Data

• Hazardous Substances Data: 88909-07-3(Hazardous Substances Data)

Upstream product

• 77-95-2 D-(-)-quinic acid 
• 39856-08-1 3,4-dimethoxy-cinnamoyl chloride 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 121-33-5 vanillin 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 14737-89-4 3,4-dimethoxy-trans-cinnamic acid 

Downstream Products

• 68622-78-6 (+)-subcosine I 
• 88931-06-0 (+/-)-subcosine I 
• 89771-50-6 (+/-)-2-episubcosine II 

Relevant articles and documents

Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase

Cinnamic anhydrides have been shown to be more than reactive reagents, but they also act as inhibitors of the enzyme acetylcholinesterease (AChE). Thus, out of a set of 33 synthesised derivatives, several of them were mixed type inhibitors for AChE (from electric eel). Thus, (E)-3-(2,4-dimethoxyphenyl)acrylic anhydride (2c) showed Ki = 8.30 ± 0.94 μM and Ki′ = 9.54 ± 0.38 μM, and for (E)-3-(3-chlorophenyl)acrylic anhydride (2u) Ki = 8.23 ± 0.93 μM and Ki′ = 13.07 ± 0.46 μM were measured. While being not cytotoxic to many human cell lines, these compounds showed an unprecedented and noteworthy inhibitory effect for AChE but not for butyrylcholinesterase (BChE).

Synthesis of Mono-, Di-, and Tri-3,4-dimethoxycinnamoyl-1,5-γ-quinides

Tri-3,4-dimethoxycinnamoyl-1,5-γ-quinide was synthesized and fully characterized by a direct synthesis from quinic acid and a large excess of 3,4-dimethoxycinnamoyl chloride. Mono- and di-3,4-dimethoxycinnamoyl-1,5-γ-quinides were also obtained from the direct coupling of 1,5-γ-quinide and 3,4-dimethoxycinnamoyl chloride in different molar ratios. Moreover, a hypothetical mechanism of the direct lactonization is proposed.