102767-61-3

Basic information

• Product Name: Butanedioic acid, bis[(4-hydroxy-3-methoxyphenyl)methylene]-, (2E,3E)-
• Synonyms: Di-((E?)-vanillyliden)-bernsteinsaeure;di-((E?)-vanillylidene)-succinic acid;E,E-bis(4-hydroxy-3-methoxybenzylidene)succinic acid
• CAS NO: 102767-61-3
• Molecular Formula: C20H18O8
• Molecular Weight: 386.35200
• Mol File: 102767-61-3.mol

Chemical Properties

• CAS DataBase Reference: Butanedioic acid, bis[(4-hydroxy-3-methoxyphenyl)methylene]-, (2E,3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanedioic acid, bis[(4-hydroxy-3-methoxyphenyl)methylene]-, (2E,3E)-(102767-61-3)
• EPA Substance Registry System: Butanedioic acid, bis[(4-hydroxy-3-methoxyphenyl)methylene]-, (2E,3E)-(102767-61-3)

Safety Data

• Hazardous Substances Data: 102767-61-3(Hazardous Substances Data)

Upstream product

• 121234-82-0 bis-((E)-3-methoxy-4-methoxymethoxy-benzylidene)-succinic acid 
• 4046-02-0 ethyl 4-hydroxy-3-methoxycinnamate 
• 102767-62-4 4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid monomethyl ester 
• 77550-11-9 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-2,6-dione 
• 5533-00-6 3-methoxy-4-methoxymethoxy-benzaldehyde 

Downstream Products

• 57934-45-9 bis-((E)-4-acetoxy-3-methoxy-benzylidene)-succinic acid-anhydride 
• 102767-62-4 4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid monomethyl ester 
• 73119-35-4 2,3-bis(3,4-dimethoxybenzylidene)butanedioic acid 
• 25936-93-0 6,7-dimethoxy-1-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylic anhydride 

Relevant articles and documents

Concise synthesis of Cannabisin G

Cannabisin G (1), a naturally occurring lignanamide, was synthesized in 45% overall yield starting from 3-tert-butyl ethyl ferulate (6). An oxidative coupling by potassium ferricyanide in an alkaline media serves as the key step to construct the biphenylb

Identification and Synthesis of New Ferulic Acid Dehydrodimers Present in Grass Cell Walls

Seven isomeric dehydrodimers of ferulic acid (4-hydroxy-3-methoxycinnamic acid) have been synthesized and identified in extracts of saponified cell walls of cocksfoot, switchgrass, and suspension-cultured corn.Dehydrodimers (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid, trans-5--2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid, (Z)-β--2-methoxyphenoxy>-4-hydroxy-3-methoxycinnamic acid, (E)-3--2-methoxyphenoxy>-4-hydroxy-5-methoxycinnamic acid, (E,E)-4,4'-dihydroxy-3,5'-dimethoxy-β,3'-bicinnamic acid, 4,4'-dihydroxy-3,3'-dimethoxy-β,β'-bicinnamic acid, and trans-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid, all arise from oxidative coupling of ferulate esters in cell walls and represent products of 8-5, 8-8, 8-O-4, 4-O-5, and 5-5 radical coupling.Prior literature has acknowledged only the presence of the 5-5 coupled dehydrodimer (E,E)-4,4'-dihydroxy-5,5'-dimethoxy-3,3'-bicinnamic acid.Consequently, by measuring only a single dehydrodimer and assuming inappropriate response factors, ferulate dehydrodimers have been underestimated by factors of up to 20.Synthetic routes to all seven isomers have been developed to provide structural authentication and determination of GC response factors.

Nucleophilic reactivity of dehydrodiferulic acid bislactone

Despite reports to the contrary, dehydrodiferulic acid bislactone can readily undergo nucleophilic attack.Silylation affords the disilyl ether-disilyl ester of the corresponding bismethylenesuccinic acid.Slow dissolution of the bislactone in sodium hydrogen carbonate solution affords this parent diacid, characterised as its mono- and dimethyl esters, and by its methylation to bisveratrylidenesuccinic acid, whose anhydride on aerial oxidation yields 6,7-dimethoxy-1-(3',4'-dimethoxyphenyl)naphthalene-2,3-dicarboxylic anhydride.