60299-54-9

Basic information

• Product Name: 5,5-DIFERULICACID
• Synonyms: (2E,2'E)-3,3'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)diacrylic acid;2-Propenoic acid, 3,3'-(6,6'-dihydroxy-5,5'-dimethoxy[1,1'-biphenyl]-3,3'-diyl)bis-, (2E,2'E)-
• CAS NO: 60299-54-9
• Molecular Formula: C₂₀H₁₈O₈
• Molecular Weight: 386.35
• Mol File: 60299-54-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5,5-DIFERULICACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-DIFERULICACID(60299-54-9)
• EPA Substance Registry System: 5,5-DIFERULICACID(60299-54-9)

Safety Data

• Hazardous Substances Data: 60299-54-9(Hazardous Substances Data)

Upstream product

• 2092-49-1 6,6'-dihydroxy-5,5'-dimethoxy-biphenyl-3,3'-dicarbaldehyde 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 19813-65-1 5,5'-diformyl-3,3'-dimethoxy-[1,1'-biphenyl]-2,2'-diyl diacetate 
• 2253-47-6 5.5'-Dimethoxy-6.6'-diacetoxy-3.3'-bis-(trans-2-carboxy-vinyl)-biphenyl 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 

Relevant articles and documents

Regioselective dimerization of ferulic acid in a micellar solution

Dehydrodimers of hydroxycinnamates play an important role in the cross-linking of plant cell walls. An aqueous solution of quaternary ammonium salts with a long aliphatic chain is known to spontaneously organize itself into micelles with the ionic part at the outer sphere. It is shown that regioisomeric ferulic acid dehydrodimers can be obtained in one step from trans-ferulic acid after attachment to these micelles and using the biomimetic peroxidase-H2O2 system. The surfactant hexadecyltrimethylammonium hydroxide yielded trans-4-(4-hydroxy-3-methoxybenzylidene)-2-(4-hydroxy-3-methoxyphenyl)-5- oxotetrahydrofuran-3-carboxylic acid (25%), (E, E)-4,4′-dihydroxy-5,5′-dimethoxy-3,3′-bicinnamic acid (21%), and trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxyphenyl)7-methoxy-2,3- dihydrobenzofuran-3-carboxylic acid (14%), whereas the surfactant tetradecyltrimethyl-ammonium bromide gave 4-cis, 8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione (18%) as the main product. The use of micelles appears to be not only a new way to synthesize regioisomeric ferulic acid dehydrodimers but may also help to understand the regiospecificity of dimeric hydroxycinnamate formation in vivo.

Convenient preparation and quantification of 5,5′-diferulic acid

5,5′-Diferulic acid (5,5′-DFA), which is one of the cross-linking residues in plant cell walls, was prepared by using a facile procedure. The phenol oxidation of vanillin with Fe Cl3 gave divanillin, which was further devoted to a Perkin reaction to give the desired product. It was found on 13C-NMR that the chemical shift of C-5 of ferulic acid (FA) clearly shifted downfield, when this carbon is quaternarized by the oxidative dimerizaton to 5,5′-DFA, while those of other carbons of 5,5′-DFA are fundamentally same as those of FA. Also prepared was [9,9′-13C2]-5,5′-DFA, which was proved to be a good internal standard on GC-MS quantification of endogenous 5,5′-DFA from plant tissues.