60299-54-9Relevant articles and documents
Regioselective dimerization of ferulic acid in a micellar solution
Larsen, Erik,Andreasen, Mette F.,Christensen, Lars P.
, p. 3471 - 3475 (2001)
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.
Structural modification of phenylpropanoid-derived compounds and the effects on their participation in redox processes
Russell, Wendy R.,Scobbie, Lorraine,Chesson, Andrew
, p. 2537 - 2546 (2007/10/03)
Oxidation and reduction processes are fundamental to many of the proposed mechanisms by which dietary phytochemicals are thought to exert protective effects against cardiovascular disease and some cancers. An understanding of the redox chemistry of these compounds is essential in assessing their potential to participate in these processes. Phenylpropanoid-derived compounds were selected and synthesised where required to represent many of the structural features found in this important group of compounds. Using electron paramagnetic resonance spectroscopy and computational chemistry a structure-redox activity relationship was obtained. Good correlation of computational and experimental results was observed for the mono-hydroxylated compounds. This demonstrated the value of computational chemistry in obtaining information about compounds, not readily available and the effect of electron delocalisation on parent radical stability. For compounds containing more than one hydroxyl, the relationship was found to be more complex. The importance of quinone formation in compounds containing more than one hydroxyl substituent was highlighted, as this was found to have a significant effect on stabilisation and therefore, their participation in redox processes.
Convenient preparation and quantification of 5,5′-diferulic acid
Yamamoto, Hirotaka,Hoshino, Tsutomu,Uchiyama, Takeo
, p. 390 - 394 (2007/10/03)
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.
