2092-49-1Relevant articles and documents
Four interpenetrating hydrogen-bonded three-dimensional networks in divanillin
Imer, Marcos R.,Aldabalde, Virginia,Pagola, Silvina,Streek, Jacco van de,Suescun, Leopoldo
, p. 1768 - 1773 (2018)
The crystal structure of divainillin (systematic name: 6,6′-dihydroxy-5,5′-dimethoxy-[1,1′-biphenyl]-3,3′-dicarbaldehyde), C16H14O6, was determined from laboratory powder X-ray diffraction data using the software EXPO2013 (direct methods) and WinPSSP (direct-space approach). Divanillin molecules crystallize in the orthorhombic space group Pba2 (No. 32), with two molecules per unit cell (Z′ =). Each divanillin molecule, with twofold symmetry, is linked through strong alcohol–aldehyde hydrogen bonds to four equivalent molecules, defining a three-dimensional hydrogen-bonding network, with rings made up of six divanillin units (a diamond-like arrangement). Each molecule is also connected through π–π interactions to a translation-equivalent molecule along c. Four consecutive molecules stacked along [001] belong to four different three-dimensional hydrogen-bonding networks defining a quadruple array of interpenetrating networks. This complex hydrogen-bonding array is proposed as an explanation for the aging process experienced by divanillin powders.
Electrochemical synthesis of biobased polymers and polymer building blocks from vanillin
Kunkel, Robin,Schmidt, Volkmar M.,Cremers, Carsten,Müller, Dominik,Schmiedl, Detlef,Tübke, Jens
, p. 8970 - 8985 (2021)
Vanillin, one of the few biobased aromatic compounds available on an industrial level, is an attractive candidate for the synthesis of biobased polymers and polymer building blocks. This study presents a detailed investigation of the reductive electrochemical coupling process by pinacolization of vanillin and divanillin in an electrochemical H-type cell setup to the polymer building block hydrovanilloin and to polyvanillin, respectively. Therein, different cathode materials are screened by linear sweep voltammetry for their capability and activity of hydrodimerization of phenolic aromatic aldehydes in alkaline aqueous media. Product distributions and faradaic efficiencies of the electrochemical vanillin reduction are investigated in bulk electrolysis experiments. Dependencies on electrochemical parameters such as current densities, applied charges and cathode materials are studied. Furthermore, the polyvanillin synthesis from divanillin is also investigated by bulk electrolysis experiments. The effects of selected electrochemical parameters (current density, applied charge and electrode material) on yield and structural features (weight-average molecular weight (MW), number-average molecular weight (MN), polydispersity (MW/MN)) measured by size exclusion chromatography of the obtained polyvanillin were evaluated. Structural features of isolated polyvanillin were determined by 2D-NMR (HSQC,13C/1H) analyses and by31P-NMR analyses afterin situlabeling with Cl-TMDP and possible pathways for their generation are discussed. These two promising electro-synthetic processes studied are free of hazardous materials and reagents and highlight the contributions of preparative electrochemistry to green chemistry and further pave the way toward the application of electrochemistry in the synthesis of biobased building blocks and polymers.
5,5′-bis-vanillin derivatives as discriminating sensors for trivalent cations
Costero, Ana M.,Gil, Salvador,Parra, Margarita,Mancini, Pedro M.E.,Kneeteman, María N.,Quindt, Matías I.
, p. 3988 - 3991 (2015)
Abstract Several bis-vanillin derivatives containing semicarbazone moieties have been prepared and used in discriminating trivalent cations. The prepared probes are readily obtained and they are usually highly crystalline. Depending on the ligand and the studied cations, quenching, enhancement or no changes in the fluorescence spectrum were observed. Using a series of the prepared ligands allows distinguishing between Fe3+, Cr3+ and Al3+. Detection limits and selectivity in front of divalent cations have been evaluated.
Evaluation of antioxidant activity of vanillin by using multiple antioxidant assays
Tai, Akihiro,Sawano, Takeshi,Yazama, Futoshi,Ito, Hideyuki
, p. 170 - 177 (2011)
Background: Vanillin, a compound widely used in foods, beverages, cosmetics and drugs, has been reported to exhibit multifunctional effects such as antimutagenic, antiangiogenetic, anti-colitis, anti-sickling, and antianalgesic effects. However, results of studies on the antioxidant activity of vanillin are not consistent. Methods: We systematically evaluated the antioxidant activity of vanillin using multiple assay systems. DPPH radical-, galvinoxyl radical-, and ABTS+-scavenging assays, ORAC assay and an oxidative hemolysis inhibition assay (OxHLIA) were used for determining the antioxidant activity. Results and conclusion: Vanillin showed stronger activity than did ascorbic acid and Trolox in the ABTS+-scavenging assay but showed no activity in the DPPH radical- and galvinoxyl radical-scavenging assays. Vanillin showed much stronger antioxidant activity than did ascorbic acid and Trolox in the ORAC assay and OxHLIA. In the ABTS+-scavenging assay, ORAC assay and OxHLIA, vanillin reacted with radicals via a self-dimerization mechanism. The dimerization contributed to the high reaction stoichiometry against ABTS + and AAPH-derived radicals to result in the strong effect of vanillin. Oral administration of vanillin to mice increased the vanillin concentration and the antioxidant activity in plasma. These data suggested that antioxidant activity of vanillin might be more beneficial than has been thought for daily health care. General significance: Based on the results of the present study, we propose the addition of antioxidant capacity to the multifunctionality of vanillin.
Antiatherogenic effect of bisvanillyl-hydralazone, a new hydralazine derivative with antioxidant, carbonyl scavenger, and antiapoptotic properties
Bouguerne, Benaissa,Belkheiri, Nadji,Bedos-Belval, Florence,Vindis, Cecile,Uchida, Koji,Duran, Hubert,Grazide, Marie-Helene,Baltas, Michel,Salvayre, Robert,Negre-Salvayre, Anne
, p. 2093 - 2106 (2011)
Reactive oxygen species (ROS) generated within the vascular wall trigger low-density lipoprotein (LDL) oxidation, lipid peroxidation, and carbonyl stress that are involved in atherogenesis. We recently reported that the antihypertensive drug, hydralazine, exhibits carbonyl scavenger and antiatherogenic properties, but only moderate antioxidant activity, so that high concentrations are required for inhibiting LDL oxidation. We aimed to develop agents sharing both antioxidant and carbonyl scavenger properties. We have synthesized a new hydralazine derivative, the bisvanillyl-hydralazone (BVH). BVH strongly inhibited LDL oxidation induced by copper and by human endothelial cells (HMEC-1), and prevented the formation of macrophagic foam cells. BVH reduced both the extracellular generation of ROS (superoxide anion and hydrogen peroxide) induced by oxidized LDL (oxLDL), as well as intracellular oxidative stress and proteasome activation, NFkappaB activation, and oxLDL-mediated proinflammatory signaling. In parallel, BVH prevented the carbonyl stress induced by oxLDL on cellular proteins, and blocked the apoptotic cascade as assessed by the inhibition of Bid cleavage, cytochrome C release, and DEVDase activation. Lastly, BVH prevented atherogenesis and carbonyl stress in apoE -/- mice. In conclusion, BVH is the prototype of a new class of antioxidant and carbonyl scavenger agents designed for new therapeutical approaches in atherosclerosis. Mary Ann Liebert, Inc.
Convenient preparation and quantification of 5,5′-diferulic acid
Yamamoto, Hirotaka,Hoshino, Tsutomu,Uchiyama, Takeo
, p. 390 - 394 (1999)
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.
A selective colorimetric chemosensor for detection of Cu(II) ions in aqueous samples
Ferretti, Cristián Alejandro,Guntero, Vanina Alejandra,Gutierrez, Leandro Gabriel,Kneeteman, María Nelida,Noriega, Pablo Javier
, (2021/12/23)
In this work we report a selective colorimetric chemosensor (S) for Cu2+ ion detection in aqueous media. It has been synthesized by a condensation reaction between 1-hydrazinophtalazine and 6,60-dihydroxy-5,50dimethoxy-(1,10-biphenyl)-3,30-dicarbaldehyde. The interaction between S and Cu2+ was studied and the results showed a bathochromic shift at 420 nm in UV–Vis spectra. The absorbance enhancement of S was attributed to complex formation with Cu2+ by 2:1 stoichiometry. The proposed analytical method can be applied to Cu2+ quantification with a linear range covering from 5.0 to 315.8 μM, and can be used to routinely analyze Cu2+ in environmental aqueous samples with satisfactory results.
