2092-49-1Relevant academic research and scientific papers
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.
The early oxidative biodegradation steps of residual kraft lignin models with laccase
Crestini, Claudia,Argyropoulos, Dimitris S.
, p. 2161 - 2169 (1998)
A number of model compounds resembling the fundamental bonding patterns of residual kraft lignin, including a series of stilbenes, were incubated with laccase from Trametes versicolor in the presence and absence of delignification 'mediators' ABTS and HBT. The condensed kraft lignin model compounds seem to undergo initial degradation by laccase mainly via benzylic oxidation, demethylation and hydroxylation reactions. Phenolic 5-5', diphenylmethane and α-5 lignin models were found to be degraded mainly via side-chain oxidation reactions. Among the models studied, a phenolic stilbene was found to be the most reactive, yielding several products showing side-chain oxidation/transposition, demethoxylation and hydroxylation reactions. Non-phenolic 5-5', diphenylmethane and stilbene model compounds were found unreactive even in the presence of the laccase-mediator system. Copyright (C) 1997 Elsevier Science Ltd.
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.
Adsorption and anti-corrosion characteristics of vanillin Schiff bases on mild steel in 1 M HCl: Experimental and theoretical study
Banerjee, Priyabrata,Saha, Sourav Kr.,Satpati, Sanjoy,Suhasaria, Aditya,Sukul, Dipankar
, p. 9258 - 9273 (2020)
Herein, two Schiff base derivatives of vanillin and divanillin with 2-picolylamine, namely, 2-methoxy-4-((pyridin-2-ylmethylimino)methyl)phenol (compound A) and 3,3′-dimethoxy-5,5′-bis-((pyridin-2-ylmethylimino)methyl)-[1,1′-biphenyl]-2,2′-diol (compound B), respectively, were synthesized. Additionally, their adsorption characteristics and corrosion inhibition behavior were compared for mild steel in 1 M HCl using electrochemical impedance spectroscopy, potentiodynamic polarization and weight loss methods. Compound B was found to impart a better anti-corrosive effect (around 95% inhibition efficiency at 313 K) than compound A. The inhibitors act as effective mixed-type inhibitors and exhibit Langmuir-type adsorption behaviour. The kinetic-thermodynamic parameters together with the data obtained from density functional theory (DFT) and molecular dynamics (MD) simulations illustrate the mechanism of corrosion and mode of adsorption of both inhibitors on the metal surface. The better corrosion mitigation propensity of the dimeric form of the inhibitor (compound B) over the monomeric form (compound A) was tested experimentally and explained according to the theoretical data.
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.
Induction of axial chirality in divanillin by interaction with bovine serum albumin
Venturini, Diego,De Souza, Aguinaldo Robinson,Caracelli, Ignez,Morgon, Nelson Henrique,Da Silva-Filho, Luiz Carlos,Ximenes, Valdecir Farias
, (2017)
Vanillin is a plant secondary metabolite and has numerous beneficial health applications. Divanillin is the homodimer of vanillin and used as a taste enhancer compound and also a promissory anticancer drug. Here, divanillin was synthesized and studied in the context of its interaction with bovine serum albumin (BSA). We found that divanillin acquires axial chirality when complexed with BSA. This chiroptical property was demonstrated by a strong induced circular dichroism (ICD) signal. In agreement with this finding, the association constant between BSA and divanillin (3.3 × 105 mol-1L) was higher compared to its precursor vanillin (7.3 × 104 mol-1L). The ICD signal was used for evaluation of the association constant, demonstration of the reversibility of the interaction and determination of the binding site, revealing that divanillin has preference for Sudlow's site I in BSA. This property was confirmed by displacement of the fluorescent markers warfarin (site I) and dansyl-L-proline (site II). Molecular docking simulation confirmed the higher affinity of divanillin to site I. The highest scored conformation obtained by docking (dihedral angle 242°) was used for calculation of the circular dichroism spectrum of divanillin using Time-Dependent Density Functional Theory (TDDFT). The theoretical spectrum showed good similarity with the experimental ICD. In summary, we have demonstrated that by interacting with the chiral cavities in BSA, divanillin became a atropos biphenyl, i.e., the free rotation around the single bound that links the aromatic rings was impeded. This phenomenon can be explained considering the interactions of divanillin with amino acid residues in the binding site of the protein. This chiroptical property can be very useful for studying the effects of divanillin in biological systems. Considering the potential pharmacological application of divanillin, these findings will be helpful for researchers interested in the pharmacological properties of this compound.
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.
Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway
Jantaree, Phatcharida,Lirdprapamongkol, Kriengsak,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Choowongkomon, Kiattawee,Atjanasuppat, Korakot,Ruchirawat, Somsak,Svasti, Jisnuson
, p. 2299 - 2306 (2017)
The spread of cancer cells to distant organs, in a process called metastasis, is the main factor that contributes to most death in cancer patients. Vanillin, the vanilla flavoring agent, has been shown to suppress metastasis in a mouse model. Here, we evaluated the antimetastatic potential of the food additive divanillin, the homodimer of vanillin, and their structurally related compounds, apocynin and diapocynin, in hepatocellular carcinoma cells. The Transwell invasion assay showed that the dimeric forms exhibited a potency higher than those of vanillin and apocynin in inhibiting invasion, with IC50 values of 23.3 ± 7.4 to 41.3 ± 4.2 μM for the dimers, which are 26-34-fold lower than IC50 values of vanillin and apocynin (p 0.05). Both monomeric and dimeric forms target regulation of the invasion process by inhibiting phosphorylation of FAK and Akt. Molecular docking studies suggested that the dimers should bind more tightly than vanillin and apocynin to the Y397 pocket of the FAK FERM domain. Thus, the food additive divanillin has antimetastatic potential greater than that of the flavoring agent 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.
Selective laccase-catalyzed dimerization of phenolic compounds derived from lignin: Towards original symmetrical bio-based (bis) aromatic monomers
Llevot, Audery,Grau, Etienne,Carlotti, Stéphane,Grelier, Stéphane,Cramail, Henri
, p. 34 - 41 (2016)
A laccase-catalyzed process was developed to prepare, selectively, in high yield, dimers of lignin-based phenolic compounds without any purification. The influence of experimental parameters such as laccase loading, nature of solvent and the presence of oxygen on the conversion of vanillin was investigated. After the dimerization, the product obtained as a precipitate is filtered off and the solution containing the enzyme can be re-used several times, which improves the process economics. A phenolic-substrate screening reveals that such process enables to dimerize regioselectively, six ortho-methoxy-para-substituted phenols (vanillin, 4-hydroxy-3-methoxybenzonitrile, acetovanillon, methyl vanillate, 2-methoxy-4-methylphenol, and eugenol) with yields ranging from 87% to 96% and one ortho-disubstituted phenol (2,6-dimethoxyphenol) with 80% yield.
