Journal articles: 'Vanilline'

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Iskandar, Damayanti, and Susy Yunita Prabawati. "Synthesis of Compounds Acetyl Vanilat as Analgesic Compound Components." Jurnal ILMU DASAR 17, no. 2 (February 1, 2017): 73. http://dx.doi.org/10.19184/jid.v17i2.2683.

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Acetyl vanillate was synthesized to become an analgesic compound was conducted in two stages.The first stage is oxidation vanillin using Tollens reagent. The result of the oxidation wascharacterized by melting point and FTIR. The second stage, vanillic acid was acetylated usingacetic acid anhydrous under two conditions, that are acid and base using H2SO4 and NaOH 10%,respectively. Two difference products from those processes were characterized using FTIR and1H-NMR. The result of the melting point vanillic acid test showed 204°C and the standard is210°C. Vanilline was successfully oxidized, based on comparison FTIR spectra between vanillineand its precursor that showed no functional group of C-H aldehyde at 2,700-2,800 cm-1. Thecharacteristics FTIR spectra under base conditions showed no absorption of functional group ‒OHthat substituted by an acetyl group. So that, the base catalyst indicated no product of the expectedcompound. The product under acidic compounds have the characteristic yellow crystals with amelting point of 130°C. Characteristics of FTIR showed no width absorption at wave number 3400cm-1 and evidenced by 1H-NMR spectra. Shift peak at 2.342 ppm was an absorption acetylcompounds. It was concluded that acetylation of acetyl vanillate compounds under acidicconditions to produce the expected product.Keywords: vanilin, vanilic acid, acetylation

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Chatonnet, Pascal, Jean-Noël Boidron, Denis Dubourdieu, and Monique Pons. "Evolution de certains composés volatils du bois de chêne au cours de son séchage premiers résultats." OENO One 28, no. 4 (December 31, 1994): 359. http://dx.doi.org/10.20870/oeno-one.1994.28.4.1720.

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Pendant le séchage des merrains sur parc à l'air libre, on assiste à une profonde modification de la composition chimique et du profil aromatique du bois de chêne. La teneur en eugénol, en aldéhydes phénols et en Β-méthyl-y-octalactone augmente régulièrement pendant le vieillissement du bois. Principalement sous forme trans au début du séchage, la Β-méthyl-y-octalactone s'accumule finalement sous la forme cis plus aromatique. Dans le même temps, on observe également une accumulation importante du précurseur inodore de Β-méthyl-y-octalactone. L'intervention des micro-organismes fréquemment isolés sur le bois en cours de séchage naturel sur la formation de composés aromatiques a été étudiée. La culture de diverses moisissures isolées de bois en cours de séchage naturel sur extraits de bois et directement sur sciure de chêne aboutit dans tous les cas à une forte diminution des teneurs en aldéhydes phénols, notamment de la vanilline. En effet, tous les micro-organismes étudiés (Penicilium sp., Trichoderma sp., Aureobasidium sp.) sont incapables de dégrader la lignine car ils ne possèdent pas d'activité ligninase. En revanche, ces champignons possèdent une forte activité oxydo-réductase capable de réduire la vanilline en alcool vanillique inodore. En conséquence, les aldéhydes phénols apparaissant au cours du séchage naturel du merrain ne dérivent pas d'une attaque enzymatique mais plus vraisemblablementde l'acidolyse et de l'oxydation chimique de la lignine du bois. Le stockage du bois à l'air libre en présence d'eau et d'oxygène doit permettre une évolution favorable de son potentiel aromatique tant que la vanilline et la cis Β-méthyly-octalactone s'accumulent.

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Kamaal, Saima, Md Serajul Haque Faizi, Arif Ali, Musheer Ahmad, Mayank Gupta, Necmi Dege, and Turganbay Iskenderov. "Crystal structure of 4-[(2-hydroxy-3-methoxybenzyl)amino]benzoic acid hemihydrate." Acta Crystallographica Section E Crystallographic Communications 75, no. 2 (January 8, 2019): 159–62. http://dx.doi.org/10.1107/s2056989018018455.

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In the crystal of the title vanilline derivative, 2C15H15NO4·H2O, the secondary amine molecule is accompanied by half equivalent of water. The molecule is non-planar, with torsion angle Caryl—CH2—NH—Caryl of −83.9 (2)°. In the crystal, the system of O—H...O hydrogen bonds, including bridging water molecules residing on crystallographic twofold axes, results in a two-dimensional layered structure. Within the layers, there are also weak N—H...π interactions involving the vanilline benzene ring.

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Onozaki, Hiromichi, Hisaye Asai, Shinobu Isshiki, and Hideo Esaki. "Bacterial metabolism of vanillylamine and vanilline." Journal of Fermentation Technology 64, no. 5 (October 1986): 470. http://dx.doi.org/10.1016/0385-6380(86)90041-5.

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Yue, Yongkang, Fangjun Huo, Caixia Yin, Jianbin Chao, Yongbin Zhang Yongbin Zhang, and Xing Wei. "An ICT based ultraselective and sensitive fluorescent probe for detection of HClO in living cells." RSC Advances 5, no. 95 (2015): 77670–72. http://dx.doi.org/10.1039/c5ra16097a.

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An ICT based ultraselective and sensitive probe for colorimetric and fluorescent detection of HClOviaoxidative cleavage of an alkene linker to epoxide and then to aldehydes was developed through the conjugation of pyridinium with vanilline.

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Kim, Taehyeong, Heeseok Jeong, Suji Park, and Gyungmin Kim. "Anti-mold Activity of Vanillin and o-Vanillin for the Production of Anti-mold Wallpaper." Korean Science Education Society for the Gifted 15, no. 1 (April 30, 2023): 122–35. http://dx.doi.org/10.29306/jseg.2023.15.1.122.

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Molds are toxic and harmful to the human body. In this study, we intended to produce anti-mold wallpaper using easily obtained substances. First, four strains were separated and identified from actual moldy wallpaper. Next, Vanillin and o-Vanillin were both selected as anti-mold substances due to the fact that they were confirmed to have growth-inhibitory effects on the four identified strains. For all the strains, the growth inhibitory effect of o-Vanillin was higher than Vanillin. It was verified that the higher the treatment concentration of Vanillin and o-Vanillin, the higher the ROS production in all fungi, which means the anti-mold activity of Vanillin and o-Vanillin is related to the increase in ROS production. Vanillin and o-Vanillin were smeared on the wallpaper to confirm this anti-mold effect. Mold growth was suppressed in the wallpaper treated with Vanillin of 0.05M or more and o-Vanillin of 0.01M or more, but at concentrations below that, the growth of the mold did not differ significantly from the control group. The cytotoxicity of Vanillin and o-Vanillin was directly proportional to the concentration of the treated candidate substances, and the cytotoxicity of o-Vanillin was higher than that of Vanillin. Therefore, it would be appropriate to apply Vanillin of 0.05M or less for the use of anti-mold wallpaper. Based on its stronger anti-mold activity when compared to anti-mold drugs on the market, Vanillin can be used in a wide variety of places, including anti-mold sprays and paints.

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ROSU, Tudor, Angela KRIZA, Viorel CARCU, and Anca NICOLAE. "TRANSITION METAL COMPLEXES OF THE FORMYL VANILLINE DERIVATIVES LIGAND FAMILY." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 5, no. 5 (December 20, 1997): 67–77. http://dx.doi.org/10.48141/sbjchem.v5.n5.1997.68_1997.pdf.

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Divalent 3d metal complexes with formyl-vanilline derivatives, of lite type ML2 or ML2X2 (M = Cu(II), Co(II); X = Cl), were sythesized by reaction of the corresponding metal(II) chlorides with 1-[3-formyl-4-methoxy-6-hidroxybemilydene]-2-phenazinoyllhydrazine, (FDFH), 1-benzilydene-2-phenazinoyhydrazine, (BFH), and 3-formyl-5,6-dihydroxybemilydenc-2-nitro-1--methylaniline, (FBAH). The novel complexes were characterized by ESR, IR, electronic spectroscopy, molar electric conductibility measurements and magnctk studies. These compounds appear to bn hexacoordinated.

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Kozlov, N. G., and L. I. Basalaeva. "Vanilline Alkanoates in the Synthesis of Hexahydrobenzacridine and Octahydroxanthene Derivatives." Russian Journal of General Chemistry 75, no. 4 (April 2005): 617–21. http://dx.doi.org/10.1007/s11176-005-0282-2.

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9

Böeseken, J., and J. Greup. "L'Oxydation de Quelques Dérivés de la Vanilline par L'acide Peracétique." Recueil des Travaux Chimiques des Pays-Bas 58, no. 6 (September 3, 2010): 528–37. http://dx.doi.org/10.1002/recl.19390580608.

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10

Monties, Bernard. "Composition chimique des bois de chêne: composés phénoliques, relations avec quelques propriétés physiques et chimiques susceptibles d'influencer la qualité des vins et des eaux-de-vie." OENO One 21, no. 3 (September 30, 1987): 169. http://dx.doi.org/10.20870/oeno-one.1987.21.3.1282.

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Les polyphénols du bois de chêne, extractibles et composés liés à la paroi végétale = lignines, lignanes, tanins et aldéhydes phénoliques, ont été envisagés au niveau moléculaire de leurs relations avec les propriétés physico-chimiques des bois : retrait, porosité, propriétés mécaniques.Des résultats originaux ont été aussi présentés concernant le fractionnement des polyphénols pariétaux, l'incrustation des parois par les tanins hydrolysables: acide ellagique associé à des fractions de lignine, ainsi que la formation d'aldéhydes phénoliques (vanilline, syringaldéhyde, aldéhydes coniférylique et sinapylique) par pyrolyse douce de la lignine. Des mécanismes réactionnels hypothétiques ont été suggérés.+++Oak wood phenolics, extractives and cell wall linked compounds : lignins, lignans, tanins and phenolic aldehydes have been discussed, at the molecular level, in their relations with physico-chemical properties of wood = shrinking, permeability and mechanical properties.Unpublished results have been also reported concerning fractionnation of cell wall phenolics, incrustation of cell wall by tanins: ellagic acid associated with lignins fractions and formation of phenolic aldehydes (vanillin, syringaldehyde, coniferaldehyde, sinapaldehyde) during mild pyrolysis of lignin in oak wood. Hypotherical reaction mechanism have been suggested.

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YEMIŞ, GÖKÇE POLAT, FRANCO PAGOTTO, SUSAN BACH, and PASCAL DELAQUIS. "Effect of Vanillin, Ethyl Vanillin, and Vanillic Acid on the Growth and Heat Resistance of Cronobacter Species." Journal of Food Protection 74, no. 12 (December 1, 2011): 2062–69. http://dx.doi.org/10.4315/0362-028x.jfp-11-230.

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Preservatives could be part of an effective intervention strategy for the control of Cronobacter species in foods, but few compounds with the desired antimicrobial properties have been identified to date. We examined the antibacterial activity of vanillin, ethyl vanillin, and vanillic acid against seven Cronobacter spp. in quarter-strength tryptic soy broth with 5 g/liter yeast extract (TSBYE) adjusted to pH 5.0, 6.0, and 7.0 at 10, 21, and 37°C. All compounds exhibited pH- and temperature-dependant bacteriostatic and bactericidal activity. MICs of vanillin and ethyl vanillin consistently increased with decreasing pH and temperature, but vanillic acid had little activity at pH values of 6.0 and 7.0. The MICs for all temperatures, pH values, and bacterial strains tested were 2 mg/ml ethyl vanillin, 3 mg/ml vanillin, and >8 mg/ml vanillic acid. MBCs also were influenced by pH, although significantly higher concentrations were needed to inactivate the bacteria at 21°C than at 10 or 37°C. Survivor curves for Cronobacter sakazakii strains at the MBCs of each compound revealed that all treatments resulted in immediate loss of cell viability at 37°C. Measurements of propidium iodide uptake indicated that the cell membranes were damaged by exposure to all three compounds. The thermal resistance of C. sakazakii was examined at 58°C in TSBYE supplemented with MBCs of each compound at pH 5.0 and 6.0. D-values at pH 5.0 were reduced from 14.56 ± 0.60 min to 0.93 ± 0.01, 0.63 ± 0.01, and 0.98 ± 0.02 min for vanillin, ethyl vanillin, and vanillic acid, respectively. These results suggest that vanillin, ethyl vanillin, and vanillic acid may be useful for the control of Cronobacter spp. in food during preparation and storage.

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DELAQUIS, PASCAL, KAREEN STANICH, and PETER TOIVONEN. "Effect of pH on the Inhibition of Listeria spp. by Vanillin and Vanillic Acid." Journal of Food Protection 68, no. 7 (July 1, 2005): 1472–76. http://dx.doi.org/10.4315/0362-028x-68.7.1472.

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The antimicrobial effects of vanillin and vanillic acid were verified against several species and strains of Listeria monocytogenes, Listeria innocua, Listeria grayi, and Listeria seeligeri in a laboratory medium adjusted to pH values ranging from 5.0 to 8.0. Medium pH had little influence on the MIC of vanillin as determined by a broth dilution assay, and growth of all test strains was inhibited by concentrations ranging from 23 to 33 mM. In contrast, none of the strains were inhibited by 100 mM vanillic acid at pH > 6.0, but complete inhibition was achieved at pH 5.0 with 10 mM. The effect of pH was further characterized by incubation of L. monocytogenes, L. innocua, and L. grayi in media containing 30 mM vanillin or 60 mM vanillic acid at pH 5.0, 6.0, and 7.0. Bactericidal effects increased with pH in media supplemented with vanillin. An inverse relationship was found for vanillic acid, and the lethality of the compound increased with declining pH. Mixtures of vanillin and vanillic acid exhibited additive inhibitory effects, particularly at lower pH. These natural antimicrobial compounds could prove useful either alone or in mixtures for the control of Listeria spp. in food products.

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Swami Vetha, Berwin Singh, Angela Guma Adam, and Azeez Aileru. "Redox Responsive Copolyoxalate Smart Polymers for Inflammation and Other Aging-Associated Diseases." International Journal of Molecular Sciences 22, no. 11 (May 25, 2021): 5607. http://dx.doi.org/10.3390/ijms22115607.

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Polyoxalate (POx) and copolyoxalate (CPOx) smart polymers are topics of interest the field of inflammation. This is due to their drug delivery ability and their potential to target reactive oxygen species (ROS) and to accommodate small molecules such as curcumin, vanilline, and p-Hydroxybenzyl alcohol. Their biocompatibility, ultra-size tunable characteristics and bioimaging features are remarkable. In this review we discuss the genesis and concept of oxylate smart polymer-based particles and a few innovative systemic delivery methods that is designed to counteract the inflammation and other aging-associated diseases (AADs). First, we introduce the ROS and its role in human physiology. Second, we discuss the polymers and methods of incorporating small molecule in oxalate backbone and its drug delivery application. Finally, we revealed some novel proof of concepts which were proven effective in disease models and discussed the challenges of oxylate polymers.

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Li, Tao, and John P. N. Rosazza. "Biocatalytic Synthesis of Vanillin." Applied and Environmental Microbiology 66, no. 2 (February 1, 2000): 684–87. http://dx.doi.org/10.1128/aem.66.2.684-687.2000.

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ABSTRACT The conversions of vanillic acid and O-benzylvanillic acid to vanillin were examined by using whole cells and enzyme preparations of Nocardia sp. strain NRRL 5646. With growing cultures, vanillic acid was decarboxylated (69% yield) to guaiacol and reduced (11% yield) to vanillyl alcohol. In restingNocardia cells in buffer, 4-O-benzylvanillic acid was converted to the corresponding alcohol product without decarboxylation. PurifiedNocardia carboxylic acid reductase, an ATP and NADPH-dependent enzyme, quantitatively reduced vanillic acid to vanillin. Structures of metabolites were established by 1H nuclear magnetic resonance and mass spectral analyses.

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Ingole, Ashwini, Megha P. Kadam, Aishwarya P. Dalu, Shital M. Kute, Piyusha R. Mange, Vaishali D. Theng, Om R. Lahane, et al. "A Review of the Pharmacological Characteristics of Vanillic Acid." Journal of Drug Delivery and Therapeutics 11, no. 2-S (April 15, 2021): 200–204. http://dx.doi.org/10.22270/jddt.v11i2-s.4823.

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A dihydroxybenzoic acid analog used as a flavoring agent is vanillic acid (4hydroxy-3-methoxybenzoic acid). It's a form of vanillin that has been oxidized. It's also a step in the process of making vanillin from Ferulic Acid. Vanillic acid has seen a lot of press because of its many uses in the cosmetics, fruit, flavorings, cigarettes,alcohols, drinks, and polymer sectors. It's said to have effective antioxidant, anti-inflammatory, and neuroprotective properties. The pharmacological impact on oxidative stress-induced neuro-degeneration, on the other hand, have not been thoroughly examined. The pharmacological properties of vanillic Acid lead to its possible use in the treatment of various diseases. Keywords: Vanillic acid, Pharmacological Potential, wound healing, Antioxidants

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Fleige, Christian, Gunda Hansen, Jens Kroll, and Alexander Steinbüchel. "Investigation of the Amycolatopsis sp. Strain ATCC 39116 Vanillin Dehydrogenase and Its Impact on the Biotechnical Production of Vanillin." Applied and Environmental Microbiology 79, no. 1 (October 12, 2012): 81–90. http://dx.doi.org/10.1128/aem.02358-12.

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ABSTRACTThe actinomyceteAmycolatopsissp. strain ATCC 39116 is capable of synthesizing large amounts of vanillin from ferulic acid, which is a natural cell wall component of higher plants. The desired intermediate vanillin is subject to undesired catabolism caused by the metabolic activity of a hitherto unknown vanillin dehydrogenase (VDHATCC 39116). In order to prevent the oxidation of vanillin to vanillic acid and thereby to obtain higher yields and concentrations of vanillin, the responsible vanillin dehydrogenase inAmycolatopsissp. ATCC 39116 was investigated for the first time by using data from our genome sequence analysis and further bioinformatic approaches. Thevdhgene was heterologously expressed inEscherichia coli, and the encoded vanillin dehydrogenase was characterized in detail. VDHATCC 39116was purified to apparent electrophoretic homogeneity and exhibited NAD+-dependent activity toward vanillin, coniferylaldehyde, cinnamaldehyde, and benzaldehyde. The enzyme showed its highest level of activity toward vanillin at pH 8.0 and at a temperature of 44°C. In a next step, a precisevdhdeletion mutant ofAmycolatopsissp. ATCC 39116 was generated. The mutant lost its ability to grow on vanillin and did not show vanillin dehydrogenase activity. A 2.3-times-higher vanillin concentration and a substantially reduced amount of vanillic acid occurred with theAmycolatopsissp. ATCC 39116 Δvdh::Kmrmutant when ferulic acid was provided for biotransformation in a cultivation experiment on a 2-liter-bioreactor scale. Based on these results and taking further metabolic engineering into account, theAmycolatopsissp. ATCC 39116 Δvdh::Kmrmutant represents an optimized and industrially applicable platform for the biotechnological production of natural vanillin.

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Pawar, Kranti, Ramanlal Kachave, Madhuri Kanawade, and Vinayak Zagre. "A Review on Nanoparticles Drug Delivery System." Journal of Drug Delivery and Therapeutics 11, no. 4 (July 15, 2021): 101–4. http://dx.doi.org/10.22270/jddt.v11i4.4865.

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The method or process of delivering a pharmaceutical ingredient to create a therapeutic effect in people or animals is referred to as drug delivery. Nasal and pulmonary routes of medication administration are becoming increasingly important in the treatment of human illnesses. These methods, especially for peptide and protein therapies, provide potential alternatives to parenteral drug administration. Several medication delivery methods have been developed for this purpose and are being tested for nasal and pulmonary delivery. Chitosan, Alginate, vanilline oxalate, zinc oxalate, cellulose, polymeric micelles, Gliadin, and phospholipid are examples of these. Multidrug resistance, a key issue in chemotherapy, can be reversed with these nanoparticles. Surgery, chemotherapy, immunotherapy, and radiation are all well-established treatments used in cancer treatment. A nanoparticle has emerged as a potential method for the targeted delivery of medicines used to treat certain illnesses. Keywords: Nasal Drug Delivery, Pulmonary Drug Delivery, Nanoparticles

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Budimarwanti, C., and Karim Theresih. "SYNTHESIS OF AMYL VANILLIL ETHER AS WARMING AGENT FROM VANILLIN." Jurnal Sains Dasar 4, no. 2 (May 20, 2016): 100. http://dx.doi.org/10.21831/jsd.v4i2.9084.

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Synthesis of amyl vanillyl ether from vanillin was carried out by two different methods, two-steps reaction method and one-step reaction method. In two-steps reaction method beginning with the first stage reduction of vanillin with NaBH4 to obtain vanillyl alcohol. Then, dehydration vanillyl alcohol and amyl alcohol with concentrated sulfuric acid. Synthesized compound were identification by TLC, IR spectroscopy and GCMS. In one step reaction method the vanillyl alcohol as a result of reduction of vanillin with NaBH4 are not isolated in advance, immediately reacted with amyl alcohol to form amyl vanillyl ether compound with concentrated HCl dehydrator. The results of two-steps reaction method showed that the reduction reaction of vanillin with NaBH4 produced vanillyl alcohol. Vanillyl alcohol compound that produced is white powder and yield 41.28%. Vanillyl amyl ether compound could not synthesis by dehydration from vanillyll alcohol from reduction of vanillin and amyl alcohol. Ether compound from dehydration of vanillyl alcohol from reduction of vanillin and amyl alcohol is diamyl ethers. Method one reaction step successfully synthesized amyl vanilil ether compound. Amyl vanilil ether compound that produced is liquid, colorless and yield 86.42%. Keywords: amyl vanillil ether, vanillin, vanillil alcohol, amyl alcohol

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Chen, Hao-Ping, Mindy Chow, Chi-Chun Liu, Alice Lau, Jie Liu, and Lindsay D. Eltis. "Vanillin Catabolism in Rhodococcus jostii RHA1." Applied and Environmental Microbiology 78, no. 2 (November 4, 2011): 586–88. http://dx.doi.org/10.1128/aem.06876-11.

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ABSTRACTGenes encoding vanillin dehydrogenase (vdh) and vanillateO-demethylase (vanAB) were identified inRhodococcus jostiiRHA1 using gene disruption and enzyme activities. During growth on vanillin or vanillate,vanAwas highly upregulated whilevdhwas not. This study contributes to our understanding of lignin degradation by RHA1 and other actinomycetes.

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Jamin, Eric, Frédérique Martin, Gilles G. Martin, I. Billault, A. I. Blanch-Cortès, C. Fauhl, C. Guillou, et al. "Determination of Site-Specific (Deuterium/Hydrogen) Ratios in Vanillin by 2H-NuclearMagnetic Resonance Spectrometry: Collaborative Study." Journal of AOAC INTERNATIONAL 90, no. 1 (January 1, 2007): 187–95. http://dx.doi.org/10.1093/jaoac/90.1.187.

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Abstract The results of collaborative study are reported for a method that determines the site-specific isotope ratios of deuterium/hydrogen (D/H)i in vanillin by deuterium-nuclear magnetic resonance (2H-NMR) spectrometry. This method allows characterization of all the main commercial sources of commercial vanillin and detection of undeclared mixtures. It is based on the fact that the amounts of deuterium at various positions in the vanillin molecule are significantly different from one source to another. Vanillin is dissolved in acetonitrile and analyzed with a high-field NMR spectrometer fitted with a deuterium probe and a fluorine lock. The proportions of isotopomers monodeuterated at each hydrogen position of the molecule are recorded, and the corresponding (D/H) ratios are determined by using a calibrated reference. Nine laboratories analyzed 5 materials supplied as blind duplicates (1 natural vanillin from vanilla beans, 2 synthetic vanillins from guaiacol, 1 semisynthetic vanillin from lignin, and a mixture of natural and synthetic vanillins). The precision of the method for measuring site-specific ratios was as follows: for (D/H)1 the within-laboratory standard deviation (sr) values ranged from 2.2 to 5.8 ppm, and the among-laboratories standard deviation (sR) values ranged from 3.6 to 5.1 ppm; for (D/H)3 the sr values ranged from 1.7 to 3.2 ppm, and the sR values ranged from 2.4 to 3.7 ppm; for (D/H)4 the sr values ranged from 2.3 to 6.2 ppm, and the sR values ranged from 2.4 to 6.4 ppm; for (D/H)5 the sr values ranged from 0.8 to 2.7 ppm, and the sR values ranged from 0.9 to 2.3 ppm. It was shown that these values allow a satisfactory discrimination between vanillin sources. Therefore, the Study Director recommends the method for adoption as a First Action Official Method by AOAC INTERNATIONAL.

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Xiao, Furong, Lu Chen, Jide Wang, Ronglan Wu, Fan Yue, and Jing Li. "Studies on solid state synthesis and the oxygenation property of cobalt (II) Schiff base (vanilline polyamine) complexes." Frontiers of Chemistry in China 2, no. 2 (April 2007): 169–73. http://dx.doi.org/10.1007/s11458-007-0034-4.

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Poveda-Giraldo, Jhonny A., and Carlos A. Cardona Alzate. "Biorefinery potential of Eucalyptus grandis to produce phenolic compounds and biogas." Canadian Journal of Forest Research 51, no. 1 (January 2021): 89–100. http://dx.doi.org/10.1139/cjfr-2020-0201.

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Vanillin is widely known in the food industry as the main flavoring compound of vanilla. Its natural extraction from the seed is not enough to supply the worldwide vanillin demand; therefore, new chemical routes from biomass have been developed to satisfy the vanillin market. A biorefinery for forest waste valorization could be an opportunity to maximize the economic gains and reduce the environmental impact in an integrated approach. This work demonstrates the experimental production of vanillin and vanillic acid through black liquor oxidation, after alkaline pretreatment of Eucalyptus grandis W. Hill ex Maiden chips. Additionally, the remaining solid fraction was valorized by anaerobic digestion. The experimental yields in the oxidation stage were 4.37% and 2.14% (based on lignin) for vanillin and vanillic acid, respectively. The biogas productivity in anaerobic digestion was 163 mL·g volatile solids–1. These values were the basis for the process simulation to analyze the potential for an integrated biorefinery. From an economic perspective, the process is feasible at a minimal processing scale of 8.58 t·h–1. On the other hand, the environmental assessment concludes that the environmental impact is mainly affected by the CO2 and CH4 emissions from biogas upgrading.

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Amombo Noa, Francoise M., and Gift Mehlana. "Co-crystals and salts of vanillic acid and vanillin with amines." CrystEngComm 20, no. 7 (2018): 896–905. http://dx.doi.org/10.1039/c7ce02022h.

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Vaishnav, Jasraj, and Prasad S. Variyar. "Biotransformation of Phenolic Acids by Fusarium udum E. Butler." Current Nutrition & Food Science 17, no. 1 (December 29, 2020): 75–81. http://dx.doi.org/10.2174/1573401316999200612105514.

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Background: The biotechnological generation of natural flavor compounds is rapidly expanding. Production of desired flavor compounds by biotransformation is natural, more effective, and an economical process. High economic value of bio-vanillin has led to a wide interest in research on the production of vanillin through biotechnological routes. Objective: The aim of the present study was to use F. udum E. Butler as a bio-catalyst for the production of bio-vanillin, from easily available and economically viable phenolic substrates. Method: Mycelium of fungal strain, was incubated in minimal medium with phenolic substrates. The medium was analyzed by GC/MS at specific time intervals in order to identify products formed during biotransformation on different time scales. Results: Production of bio-vanillin was observed after 24 h as the major product when F. udum E. Butler was grown on vanillic acid. Guaiacol was found to be the end product of this reaction as the further conversion of guaiacol was not observed. The metabolic pathway for vanillic acid biotransformation was also elucidated by identifying intermediate metabolites of the reaction and fate of these intermediates when these intermediates were used as a sole carbon source was also elucidated. Conclusion: Microbial production of bio-vanillin is one of the highly economically attractive biotransformation processes as substrates of this process are byproducts of agroindustrial sources. However, toxicity of vanillin accumulation is one of the major bottleneck in bio-vanillin production, and it demands serious scientific inputs.

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Mitsui, Ryoji, Yoko Kusano, Hiroya Yurimoto, Yasuyoshi Sakai, Nobuo Kato, and Mitsuo Tanaka. "Formaldehyde Fixation Contributes to Detoxification for Growth of a Nonmethylotroph, Burkholderia cepacia TM1, on Vanillic Acid." Applied and Environmental Microbiology 69, no. 10 (October 2003): 6128–32. http://dx.doi.org/10.1128/aem.69.10.6128-6132.2003.

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ABSTRACT During bacterial degradation of methoxylated lignin monomers, such as vanillin and vanillic acid, formaldehyde is released through the reaction catalyzed by vanillic acid demethylase. When Burkholderia cepacia TM1 was grown on vanillin or vanillic acid as the sole carbon source, the enzymes 3-hexulose-6-phosphate synthase (HPS) and 6-phospho-3-hexuloisomerase (PHI) were induced. These enzymes were also expressed during growth on Luria-Bertani medium containing formaldehyde. To understand the roles of these enzymes, the hps and phi genes from a methylotrophic bacterium, Methylomonas aminofaciens 77a, were introduced into B. cepacia TM1. The transformant strain constitutively expressed the genes for HPS and PHI, and these activities were two- or threefold higher than the activities in the wild strain. Incorporation of [14C]formaldehyde into the cell constituents was increased by overexpression of the genes. Furthermore, the degradation of vanillic acid and the growth yield were significantly improved at a high concentration of vanillic acid (60 mM) in the transformant strain. These results suggest that HPS and PHI play significant roles in the detoxification and assimilation of formaldehyde. This is the first report that enhancement of the HPS/PHI pathway could improve the degradation of vanillic acid in nonmethylotrophic bacteria.

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Bezerra-Filho, Carlos S. M., Joice N. Barboza, Marilia T. S. Souza, Peter Sabry, Nasser S. M. Ismail, and Damião P. de Sousa. "Therapeutic Potential of Vanillin and its Main Metabolites to Regulate the Inflammatory Response and Oxidative Stress." Mini-Reviews in Medicinal Chemistry 19, no. 20 (December 16, 2019): 1681–93. http://dx.doi.org/10.2174/1389557519666190312164355.

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Many phenolic compounds found in foods and medicinal plants have shown interesting therapeutic potential and have attracted the attention of the pharmaceutical industry as promising pharmacologically active compounds in health promotion and disease prevention. Vanillin is a phenolic aldehyde, widely used as a flavoring agent in the food, pharmaceutical, and cosmetics industries. A variety of pharmacological activities has been attributed to this compound and its main metabolites, vanillic acid and vanillyl alcohol, including their anti-inflammatory ability. The relationship of the anti- inflammatory effects of vanillin, vanillic acid, and vanillyl alcohol and their actions on oxidative stress is well established. Considering that the inflammatory process is related to several pathologies, including new diseases with few therapeutic options, and limited efficiency, the search for effective treatment strategies and discovery of new anti-inflammatory agents capable of modulating inflammation becomes necessary. Therefore, in this review, we discuss the therapeutic potential of vanillin and its main metabolites for the treatment of inflammatory diseases and their actions on redox status. In addition, the molecular docking evaluation of vanillin, its metabolites and isoeugenol were carried out into the phospholipase A2 binding site.

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Khang, Do Tan, La Hoang Anh, Pham Thi Thu Ha, Phung Thi Tuyen, Nguyen Van Quan, Luong The Minh, Nguyen Thanh Quan, et al. "Allelopathic Activity of Dehulled Rice and its Allelochemicals on Weed Germination." International Letters of Natural Sciences 58 (September 2016): 1–10. http://dx.doi.org/10.18052/www.scipress.com/ilns.58.1.

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In this study, the allelopathic potential of dehulled rice, rice, and hulls of rice on germination of weeds was evaluated in laboratory. Phenolic acids in growth media of these plants were also identified and quantified using HPLC. Identified allelochemicals were reversely tested for phytotoxic effects on germination and seedling growth of barnyardgrass, lettuce, radish and rice. The results showed that the inhibitory effects of dehulled rice were stronger than those of hulls and rice. Dehulled rice caused 66.7% and 50.6% reduction in radish root length and lettuce shoot height, respectively. Dehulled rice showed strong inhibitory effects on root length of lettuce and shoot height of radish while hulls and rice exhibited stimulation. Regarding phenolic identification, vanillin and vanillic acid were detected as allelochemicals in root exudates of rice and tested plants. The results revealed that most of the vanillin and vanillic acid treatments showed high inhibitory effects on germination rates and seedling growth of lettuce and radish, high stimulatory activity on root elongation of rice. Vanillic acid (100 ppm and 200 ppm), vanillin (100 ppm) and their mixture (200 ppm) completely inhibited survival of lettuce. The findings indicate the allelopathic potential of dehulled rice which can be used for identification of more phytotoxins to produce bioherbicides in agricultural practices.

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Khang, Do Tan, La Hoang Anh, Pham Thi Thu Ha, Phung Thi Tuyen, Nguyen Van Quan, Luong The Minh, Nguyen Thanh Quan, et al. "Allelopathic Activity of Dehulled Rice and its Allelochemicals on Weed Germination." International Letters of Natural Sciences 58 (September 9, 2016): 1–10. http://dx.doi.org/10.56431/p-61d2tq.

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In this study, the allelopathic potential of dehulled rice, rice, and hulls of rice on germination of weeds was evaluated in laboratory. Phenolic acids in growth media of these plants were also identified and quantified using HPLC. Identified allelochemicals were reversely tested for phytotoxic effects on germination and seedling growth of barnyardgrass, lettuce, radish and rice. The results showed that the inhibitory effects of dehulled rice were stronger than those of hulls and rice. Dehulled rice caused 66.7% and 50.6% reduction in radish root length and lettuce shoot height, respectively. Dehulled rice showed strong inhibitory effects on root length of lettuce and shoot height of radish while hulls and rice exhibited stimulation. Regarding phenolic identification, vanillin and vanillic acid were detected as allelochemicals in root exudates of rice and tested plants. The results revealed that most of the vanillin and vanillic acid treatments showed high inhibitory effects on germination rates and seedling growth of lettuce and radish, high stimulatory activity on root elongation of rice. Vanillic acid (100 ppm and 200 ppm), vanillin (100 ppm) and their mixture (200 ppm) completely inhibited survival of lettuce. The findings indicate the allelopathic potential of dehulled rice which can be used for identification of more phytotoxins to produce bioherbicides in agricultural practices.

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Kozlevčar, Bojan, Polonca Baškovič, Aleksej Arko, Amalija Golobič, Nives Kitanovski, and Primož Šegedin. "Copper Fixation to Guaiacyl Lignin Units by Nitrogen Donor Ligands." Zeitschrift für Naturforschung B 63, no. 5 (May 1, 2008): 481–88. http://dx.doi.org/10.1515/znb-2008-0501.

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Several new copper(II) complexes with guaiacyl lignin models vanillin (HL1) [Cu(L1)2(nia)2] (1) (nia = nicotinamide) or vanillic acid (HL2) [Cu(L2)2(nia)2] (2) [Cu2(μ-L2)4(nia)2] (3), and [Cu(L2)2(Hetam)2] (4) (Hetam = ethanolamine) were isolated and characterized. The molecular structure of complex 1 reveals bidentate vanillin (HL1) coordination via the methoxy and the deprotonated hydroxy groups. On the other hand, the vanillic acid (HL2) complexes 2 - 4 show a deprotonated carboxylate group with chelating coordination mode in 2, bridging in 3 and monodentate coordination in 4. The mononuclear complexes 1, 2 and 4 show a distorted trans octahedral coordination sphere with pairs of monodentate and chelating ligands. A replacement of the monodentate nicotinamide ligand in 2 with the bidentate ethanolamine ligand in 4 changes the coordination mode of the vanillic acid anion from bidentate (complex 2) to monodentate (complex 4). This shift inside the coordination sphere reveals different O-Cu-O Jahn-Teller axes by the vanillic acid anion in 2 and ethanolamine in 4. Empty channels are present in the crystal structure of the dinuclear complex 3, stabilized by hydrogen bonds and π-π stacking.

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Penín, Lucía, Matteo Gigli, Federica Sabuzi, Valentín Santos, Pierluca Galloni, Valeria Conte, Juan Carlos Parajó, Heiko Lange, and Claudia Crestini. "Biomimetic Vanadate and Molybdate Systems for Oxidative Upgrading of Iono- and Organosolv Hard- and Softwood Lignins." Processes 8, no. 9 (September 16, 2020): 1161. http://dx.doi.org/10.3390/pr8091161.

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Recently reported acetosolv soft- and hardwood lignins as well as ionosolv soft- and hardwood lignins were transformed into monomeric aromatic compounds using either a vanadate or a molybdate-based catalyst system. Monomers were generated with remarkable, catalyst-dependent selectivity and high depolymerisation yields via oxidative exo- and endo-depolymerisation processes. Using the vanadate–hydrogen peroxide system on acetosolv pine lignin, vanillin and isovanillin were produced as main products with depolymerisation yields of 31%. Using the molybdate system on acetosolv and ionosolv lignin, vanillic acid was the practically exclusive product, with depolymerisation yields of up to 72%. Similar selectivities, albeit with lower depolymerisation yields of around 50% under standardised conditions, were obtained for eucalyptus acetosolv lignin, producing vanillin and syringaldehyde or vanillic acid as products, by using the vanadate- or the molybdate-based systems respectively.

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Kahan, Sidney. "Liquid Chromatographic Method for Determination of Vanillin and Related Flavor Compounds in Vanilla Extract: Collaborative Study." Journal of AOAC INTERNATIONAL 72, no. 4 (July 1, 1989): 614–18. http://dx.doi.org/10.1093/jaoac/72.4.614.

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Abstract A liquid chromatographic method for determination of vanillin, vanillic acid, p-hydroxybenzaldehyde, and p-hydroxybenzoic acid was collaboratively studied. The compounds are separated on a reversephase C-8 column using an acidic 10% methanol solvent and are detected at 254 nm. Recoveries for the 4 compounds present in vanilla extract ranged from 94 to 99%. Method performance as measured by repeatability and reproducibility standard deviations (sr and sR) and relative standard deviations (RSDr and RSDR), respectively, for determination of the 4 flavor compounds in authentic and adulterated vanilla extracts were as follows: p-hydroxybenzoic acid—sr 0.29, SR 0.39, RSDr 8.98%, RSDR 11.68%; p-hydroxybenzaldehyde—sr 0.92, sR 1.20, RSDr 6.16%, RSDR 6.95%; vanillic acid—sr 0.85, sR 1.12, RSDr 7.47%, RSDR 9.97%; vanillin—sr 7.45, sR 7.50, RSDr 3.43%, RSDR 3.48%. The method has been approved interim official first action.

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Žilius, Modestas, Kristina Ramanauskienė, and Vitalis Briedis. "Release of Propolis Phenolic Acids from Semisolid Formulations and Their Penetration into the Human SkinIn Vitro." Evidence-Based Complementary and Alternative Medicine 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/958717.

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Antioxidant and free radical scavenging effects are attributed to phenolic compounds present in propolis, and when delivered to the skin surface and following penetration into epidermis and dermis, they can contribute to skin protection from damaging action of free radicals that are formed under UV and premature skin aging. This study was designed to determine the penetration of phenolic acids and vanillin into the human skinin vitrofrom experimentally designed vehicles. Results of the study demonstrated the ability of propolis phenolic acids (vanillic, coumaric, caffeic, and ferulic acids) and vanillin to penetrate into skin epidermis and dermis. The rate of penetration and distribution is affected both by physicochemical characteristics of active substances and physical structure and chemical composition of semisolid vehicle. Vanillin and vanillic acid demonstrated relatively high penetration through epidermis into dermis where these compounds were concentrated, coumaric and ferulic acids were uniformly distributed between epidermis and dermis, and caffeic acid slowly penetrated into epidermis and was not determined in dermis. Further studies are deemed relevant for the development of semisolid topically applied systems designed for efficient delivery of propolis antioxidants into the skin.

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Mpofu, Enock, Joydeep Chakraborty, Chiho Suzuki-Minakuchi, Kazunori Okada, Toshiaki Kimura, and Hideaki Nojiri. "Biotransformation of Monocyclic Phenolic Compounds by Bacillus licheniformis TAB7." Microorganisms 8, no. 1 (December 21, 2019): 26. http://dx.doi.org/10.3390/microorganisms8010026.

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Bacillus licheniformis strain TAB7 is a bacterium used as a commercial deodorizing agent for compost in Japan. In this work, its ability to biotransform the following monocyclic phenolic compounds was assessed: ferulate, vanillate, p-coumarate, caffeate, protocatechuate, syringate, vanillin, and cinnamate (a precursor for some phenolic compounds). These compounds are abundant in composting material and are reported to have allelopathic properties. They come from sources such as plant material decomposition or agro-industrial waste. Biotransformation assays were carried out in LB supplemented with 0.2 mg/mL of an individual phenolic compound and incubated for up to 15 days followed by extraction and HPLC analysis. The results showed that TAB7 could biotransform ferulate, caffeate, p-coumarate, vanillate, protocatechuate, and vanillin. It, however, had a poor ability to transform cinnamate and syringate. LC-MS/MS analysis showed that ferulate was transformed into 4-vinylguaiacol as the final product, while caffeate was transformed into 4-ethylcatechol. TAB7 genome analysis suggested that, while TAB7 may not mineralize phenolic compounds, it harbored genes possibly encoding phenolic acid decarboxylase, vanillate decarboxylase, and some protocatechuate degradation pathway enzymes, which are involved in the catabolism of phenolic compounds known to have negative allelopathy on some plants. The results thus suggested that TAB7 can reduce such phenolic compounds in compost.

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Lala, Mousikha, Malay Bhattacharya, and Arnab Sen. "Pharmacological Activity of Citrus macroptera: an overview of a medicinal plant." NBU Journal of Plant Sciences 11, no. 1 (2019): 85–100. http://dx.doi.org/10.55734/nbujps.2019.v11i01.005.

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Plants and plant parts have been extensively used as medicine from the dates of early civilization. They are low in cost and have least side effects. In India, the practice of the traditional medicinal can be traced back to 5000 B.C. Citrus macroptera (Mont.) of the family Rutaceae is a bitter fruit bearing plant commonly found in tropical and subtropical regions. It is an endangered wild plant of North-eastern India. Various parts of this plant such as leaves, bark, pulp, peel specially fruits have an immense range of medicinal importance and has been used in different kinds of ailments like fever, kidney and liver dysfunction, dyspepsia, cardiovascular disease, stroke and many more to mention. The fruit of this perennial spiny plant has potential antioxidant, cytotoxic, antimicrobial, antihypertensive, antipyretic and appetite stimulant activity. The principal phytochemical constituents of this plant are Ribalinine, Edulinine, Bergamottin, Psoralen, Marmin, Severine, Geipavarine, β-pinene, α-pinene, ρ-cimene, (E)-ocimene, vanilline, Rutin, kaempferol, sabinene, limonene, γ-terpinene and so forth. Furthurmore thrombolytic, antidiabetic, antidepressant, cardioprotective, hepatoprotective activity have been reported on this plant. This review represents a comprehensive study on the various aspects of Citrus macroptera with respect to their traditional and medicinal usage or better use as alternative medicine for various kinds of treatments.

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Hirose, Jun, Naoki Tsuda, Munetoshi Miyatake, Haruhiko Yokoi, and Jun Shimodaira. "Draft Genome Sequence of Pseudomonas sp. Strain LLC-1 (NBRC 111237), Capable of Metabolizing Lignin-Derived Low-Molecular-Weight Compounds." Genome Announcements 6, no. 16 (April 19, 2018): e00308-18. http://dx.doi.org/10.1128/genomea.00308-18.

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ABSTRACT Pseudomonas sp. strain LLC-1 (NBRC 111237), isolated from soil, metabolizes lignin-derived low-molecular-weight compounds and utilizes vanillin and vanillic acid as its sole sources of carbon. Here, we report the draft genome sequence of Pseudomonas sp. strain LLC-1.

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Kaur, Baljinder, Debkumar Chakraborty, and Balvir Kumar. "Phenolic Biotransformations during Conversion of Ferulic Acid to Vanillin by Lactic Acid Bacteria." BioMed Research International 2013 (2013): 1–6. http://dx.doi.org/10.1155/2013/590359.

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Vanillin is widely used as food additive and as a masking agent in various pharmaceutical formulations. Ferulic acid is an important precursor of vanillin that is available in abundance in cell walls of cereals like wheat, corn, and rice. Phenolic biotransformations can occur during growth of lactic acid bacteria (LAB), and their production can be made feasible using specialized LAB strains that have been reported to produce ferulic acid esterases. The present study aimed at screening a panel of LAB isolates for their ability to release phenolics from agrowaste materials like rice bran and their biotransformation to industrially important compounds such as ferulic acid, 4-ethyl phenol, vanillic acid, vanillin, and vanillyl alcohol. Bacterial isolates were evaluated using ferulic acid esterase, ferulic acid decarboxylase, and vanillin dehydrogenase assays. This work highlights the importance of lactic acid bacteria in phenolic biotransformations for the development of food grade flavours and additives.

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Belkhadem, Karima, Yihong Cao, and René Roy. "Synthesis of Galectin Inhibitors by Regioselective 3′-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis." Molecules 26, no. 1 (December 29, 2020): 115. http://dx.doi.org/10.3390/molecules26010115.

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Vanillin-based lactoside derivatives were synthetized using phase-transfer catalyzed reactions from per-O-acetylated lactosyl bromide. The aldehyde group of the vanillin moiety was then modified to generate a series of related analogs having variable functionalities in the para- position of the aromatic residue. The corresponding unprotected lactosides, obtained by Zemplén transesterification, were regioselectively 3′-O-sulfated using tin chemistry activation followed by treatment with sulfur trioxide-trimethylamine complex (Men3N-SO3). Additional derivatives were also prepared from the vanillin’s aldehyde using a Knoevenagel reaction to provide extended α, β-unsaturated carboxylic acid which was next reduced to the saturated counterpart.

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Vidal, Bernard, Josie Vardin, and Françoise Wong Pin. "Near UV Spectra of Vanillin and Vanillic Acid." Spectroscopy Letters 25, no. 5 (August 1992): 661–79. http://dx.doi.org/10.1080/00387019208020700.

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Yamamoto, Mayu, Yasuhiro Futamura, Kouki Fujioka, and Kenji Yamamoto. "Novel Production Method for Plant Polyphenol from Livestock Excrement Using Subcritical Water Reaction." International Journal of Chemical Engineering 2008 (2008): 1–5. http://dx.doi.org/10.1155/2008/603957.

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Plant polyphenol, including vanillin, is often used as the intermediate materials of the medicines and vanilla flavoring. In agriculture generally vanillin is produced from vanilla plant and in industry from lignin of disposed wood pulp. We have recently developed a method for the production of plant polyphenol with the excrement as a natural resource of lignin, of the herbivorous animals, by using the subcritical water. The method for using the subcritical water is superior to that of the supercritical water because in the latter complete decomposition occurs. We have successfully produced the vanillin, protocatechuic acid, vanillic acid, and syringic acid in products. Our method is simpler and more efficient not only because it requires the shorter treatment time but also because it releases less amount of carbon dioxide into the atmosphere.

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Mohd Rifaie, Raisatul Mirza, and Latiffah Karim. "Production of Vanillin from Pumpkin Peels via Microbiological Fermentation using Aspergillus niger." Malaysian Journal of Fundamental and Applied Sciences 19, no. 6 (December 4, 2023): 1119–30. http://dx.doi.org/10.11113/mjfas.v19n6.3193.

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Vanilla is the main natural flavouring agent used in industries such as pharmaceuticals, food, flavouring, and fragrance, in which vanillin is the major component. Vanillin (4-hydroxy-3-methoxybenzaldehyde) is a secondary metabolite of plants and the major organoleptic aroma component of natural vanilla. The vanillin compound can be produced using the following routes: direct vanilla bean extraction, chemical synthesis, and biotechnological processes (bio-vanilla production). Nowadays, the chemical synthesis method used for vanillin production has been rejected by the United States and European legislation, while plant-derived vanillin is expensive. The current study demonstrates vanillin production from pumpkin peels (Cucurbita moschata) by Aspergillus niger via one-step fermentation approach. This study implements different concentrations of sodium hydroxide (1.0 M and 2.0 M) during alkaline hydrolysis pretreatment and different feeding volumes of hydrolysates during the biotransformation processes of ferulic acid into vanillin, classified as small feeding volumes (SFV) and large feeding volumes (LFV). Detection and quantification analysis were carried out using high performance liquid chromatography (HPLC), resulting in vanillin yield of 0.49 mg/L (1.0 M SFV), 0.5 mg/L (1.0 M LFV), 0.33 mg/L (2.0 M SFV), 0.59 mg/L (2.0 M LFV). Analysis with ultraviolet-visible (UV-VIS) spectrophotometry using thiobarbituric acid as reagent was carried out as well, resulting in vanillin yield of 2.76 µg/ml (1.0 M SFV), 3.78 µg/ml (1.0 M LFV), 2.68 µg/ml (2.0 M SFV), 3.05 µg/ml (2.0 M LFV). In conclusion, pumpkin peels can be considered a great source of ferulic acid and Aspergillus niger was reported as an efficient fungus in converting ferulic acid to vanillic acid, which will then be transformed into vanillin.

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Bueno, Mónica, Julián Zapata, Laura Culleré, Ernesto Franco-Luesma, Arancha de-la-Fuente-Blanco, and Vicente Ferreira. "Optimization and Validation of a Method to Determine Enolones and Vanillin Derivatives in Wines—Occurrence in Spanish Red Wines and Mistelles." Molecules 28, no. 10 (May 22, 2023): 4228. http://dx.doi.org/10.3390/molecules28104228.

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Understanding the chemical nature of wine aroma demands accurate quantitative determinations of different odor-active compounds. Quantitative determinations of enolones (maltol, furaneol, homofuraneol, and sotolon) and vanillin derivatives (vanillin, methyl vanillate, ethyl vanillate, and acetovanillone) at low concentrations are complicated due to their high polarity. For this reason, this paper presents an improved and automated version for the accurate measure of these common trace wine polar compounds (enolones and vanillin derivatives). As a result, a faster and more user-friendly method with a reduction of organic solvents and resins was developed and validated. The optimization of some stages of the solid phase extraction (SPE) process, such as washing with an aqueous solution containing 1% NaHCO3 at pH 8, led to cleaner extracts and solved interference problems. Due to the polarity of these type of compounds, an optimization of the large volume injection was also carried out. Finally, a programmable temperature vaporization (PTV) quartz glass inlet liner without wool was used. The injector temperature was raised to 300 °C in addition to applying a pressure pulse of 180 kPa for 4 min. Matrix effects were solved by the use of adequate internal standards, such as ethyl maltol and 3′,4′-(methylenedioxy)acetophenone. Method figures of merit were highly satisfactory: good linearity (r2 > 0.98), precision (relative standard deviation, RSD < 10%), high recovery (RSD > 89%), and low detection limits (<0.7 μg/L). Enolones and vanillin derivatives are associated with wine aging. For this reason, the methodology was successfully applied to the quantification of these compounds in 16 Spanish red wines and 12 mistelles. Odor activity values (OAV) indicate that furaneol should be considered an aroma impact odorant in red wines and mistelles (OAV > 1) while homofuraneol and sotolon could also produce changes in their aroma perceptions (0.1 < OAV < 1).

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Kahan, Sidney, Dana A. Krueger, R. Berger, A. Filandro, L. R. Hageman, T. Korpinski, S. Lin, N. E. Lally, M. Parrish, and K. L. Schoen. "Liquid Chromatographic Method for Determination of Vanillin and Ethyl Vanillin in Imitation Vanilla Extract (Modification of AOAC Official Method 990.25): Collaborative Study." Journal of AOAC INTERNATIONAL 80, no. 3 (May 1, 1997): 564–70. http://dx.doi.org/10.1093/jaoac/80.3.564.

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Abstract A collaborative study of a method for analysis of vanillin and ethyl vanillin in fortified and imitation vanilla flavors was performed. The method, which is an extension of AOAC Official Method 990.25, Vanillin, Vanillic Acid, p-Hydroxybenzaldehyde, and p-Hydroxybenzoic Acid in Vanilla Extract, Liquid Chromatographic Method, involves reversed-phase high-pressure liquid chromatography (LC) of the sample on a Cβ column with a water-methanol-acetic acid (89 + 10 + 1) mobile phase and UV detection at 254 nm. The method yields good recoveries of vanillin at 484 and 723 mg/100 mL and of ethyl vanillin from 37 to 400 mg/100 mL. For vanillin, repeatability (r) values were 8 mg/100 mL at a level of 155 mg/100 mL, 12 mg/100 mLat a level of 484 mg/100 mL, and 31 mg/100 mL at a level of 723 mg/100 mL. Reproducibility (R) values were 20 mg/100 mL, 55 mg/100 mL, and 137 mg/100 mL over the same range. For ethyl vanillin, r values were 2.4 mg/100 mL at a level of 37 mg/100 mL, 3.2 mg/100 mL at a level of 74 mg/100 mL, and 8.6 mg/100 mL at a level of 180 mg/100 mL. R values were 6.4 mg/100 mL, 5.4 mg/100 mL, and 22.0 mg/100 mL over the same range. AOAC Official Method 990.25 has been modified to include determination of ethyl vanillin in vanilla extract and artificial vanilla flavor.

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Civolani, Claudio, Paolo Barghini, Anna Rita Roncetti, Maurizio Ruzzi, and Alma Schiesser. "Bioconversion of Ferulic Acid into Vanillic Acid by Means of a Vanillate-Negative Mutant of Pseudomonas fluorescens Strain BF13." Applied and Environmental Microbiology 66, no. 6 (June 1, 2000): 2311–17. http://dx.doi.org/10.1128/aem.66.6.2311-2317.2000.

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ABSTRACT From a ferulic-acid-degrading Pseudomonas fluorescensstrain (BF13), we have isolated a transposon mutant, which retained the ability to bioconvert ferulic acid into vanillic acid but lost the ability to further degrade the latter acid. The mutant, BF13-97, was very stable, and therefore it was suitable to be used as a biocatalyst for the preparative synthesis of vanillic acid from ferulic acid. By use of resting cells we determined the effect on the bioconversion rate of several parameters, such as the addition of nutritional factors, the concentration of the biomass, and the carbon source on which the biomass was grown. The optimal yield of vanillic acid was obtained with cells pregrown on M9 medium containing p-coumaric acid (0.1% [wt/vol]) as a sole carbon source and yeast extract (0.001% [wt/vol]) as a source of nutritional factors. Under these conditions, 1 mg (wet weight) of biomass produced 0.23 mg of vanillic acid per h. The genomic region of BF13-97 flanking the transposon's site of insertion was cloned and sequenced revealing two open reading frames of 1,062 (vanA) and 954 (vanB) bp, respectively. The van genes are organized in a cluster and encode the subunits of the vanillate-O-demethylase, which catalyzes the first step of the vanillate catabolism. Amino acid sequences deduced from vanA and vanB genes were shown to have high identity with known VanAs and VanBs fromPseudomonas and Acinetobacter spp. Highly conserved regions known to exist in class IA oxygenases were also found in the vanillate-O-demethylase components from P. fluorescens BF13. The terminal oxygenase VanA is characterized by a conserved Rieske-type [2Fe-2S]R ligand center. The reductase VanB contains a plant-type ferredoxin [2Fe-2S]Fd, flavin mononucleotide, and NAD-ribose binding domains which are located in its C-terminal and N-terminal halves, respectively. Transfer of wild-type vanAB genes to BF13-97 complemented this mutant, which recovered its ability to grow on either vanillic or ferulic acid.

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Longe, Lionel, Gil Garnier, and Kei Saito. "Synthesis of Lignin-based Phenol Terminated Hyperbranched Polymer." Molecules 24, no. 20 (October 16, 2019): 3717. http://dx.doi.org/10.3390/molecules24203717.

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In this work, we proved the efficient synthesis of a bio-based hyper-branched polyphenol from a modified lignin degradation fragment. Protocatechuic acid was readily obtained from vanillin, a lignin degradation product, via alkaline conditions, and further polymerised to yield high molecular weight hyperbranched phenol terminated polyesters. Vanillic acid was also subjected to similar polymerisation conditions in order to compare polymerisation kinetics and differences between linear and hyperbranched polymers. Overall, protocatechuic acid was faster to polymerise and more thermostable with a degradation temperature well above linear vanillic acid polyester. Both polymers exhibited important radical scavenging activity (RSA) compared to commercial antioxidant and present tremendous potential for antioxidant applications.

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Noubigh, Adel. "Thermodynamic modeling of the solid-liquid equilibrium of two phenolic compounds in several solvents at temperatures ranging from 283.15 K to 323.15 K." Bulletin of the Chemical Society of Ethiopia 38, no. 3 (March 12, 2024): 799–810. http://dx.doi.org/10.4314/bcse.v38i3.19.

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The solubility of two natural phenolic compounds (vanillic acid (VA) and vanillin (V)) in four individual solvents (ethanol, butan-2-ol, ethylene glycol, and ethyl acetate) was measured using the gravimetric method from 283.15 to 323.15 K at atmospheric pressure. The optimization of the complexes between VA–solvents and V–solvents using the B3LYP theoretic technique and the 6-31+G (d, p) basis set indicated that the absolute value of interaction energy was higher, suggesting that the interaction between solute and the solvent was stronger. In addition, two excellent activity coefficient models (NRTL and Wilson) were used to correlate and evaluate the equilibrium solubility results. The highest relative average deviation and root-mean-square deviation values for VA are 4.36% and 3.09 × 10-3, respectively, and 3.35% and 5.52 × 10-3 for V. Furthermore, the excess enthalpy of the solution was determined on the basis of thermodynamic relations and the Wilson model. The findings indicate that the dissolution process was endothermic. KEY WORDS: Solid-liquid equilibrium, Vanillin, Vanillic acid, NRTL and Wilson models, Thermodynamic parameters Bull. Chem. Soc. Ethiop. 2024, 38(3), 799-810. DOI: https://dx.doi.org/10.4314/bcse.v38i3.19

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46

Morabbi Heravi, Kambiz, Julian Lange, Hildegard Watzlawick, Jörn Kalinowski, and Josef Altenbuchner. "Transcriptional Regulation of the Vanillate Utilization Genes (vanABKOperon) of Corynebacterium glutamicum by VanR, a PadR-Like Repressor." Journal of Bacteriology 197, no. 5 (December 22, 2014): 959–72. http://dx.doi.org/10.1128/jb.02431-14.

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Corynebacterium glutamicumis able to utilize vanillate, the product of lignin degradation, as the sole carbon source. The vanillate utilization components are encoded by thevanABKoperon. ThevanAandvanBgenes encode the subunits of vanillateO-demethylase, converting vanillate to protocatechuate, while VanK is the specific vanillate transporter. ThevanABKoperon is regulated by a PadR-type repressor, VanR. Heterologous gene expression and variations of thevanRopen reading frame revealed that the functional VanR contains 192 residues (21 kDa) and forms a dimer, as analyzed by size exclusion chromatography.In vivo, ferulate, vanillin, and vanillate induced PvanABKinC. glutamicum, while only vanillate induced the activity of PvanABKinEscherichia colilacking the ferulate catabolic system. Differential scanning fluorimetry verified that vanillate is the only effector of VanR. Interaction between the PvanABKDNA fragment and the VanR protein had an equilibrium dissociation constant (KD) of 15.1 ± 1.7 nM. The VanR-DNA complex had a dissociation rate constant (Kd) of (267 ± 23) × 10−6s−1, with a half-life of 43.5 ± 3.6 min. DNase I footprinting localized the VanR binding site at PvanABK, extending from +9 to +45 on the coding strand. Deletion of the nucleotides +18 to +27 inside the VanR binding site rendered PvanABKconstitutive. Fusion of the T7 promoter and the wild-type VanR operator, as well as its shortened versions, indicated that the inverted repeat AACTAACTAA(N4)TTAGGTATTT is the specific VanR binding site. It is proposed that the VanR-DNA complex contains two VanR dimers at the VanR operator.

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Baré, G., V. Delaunois, R. Rlkir, and Ph Thonart. "Bioconversion of vanillin into vanillic acid byPseudomonas fluorescens strain BTP9." Applied Biochemistry and Biotechnology 45-46, no. 1 (March 1994): 599–610. http://dx.doi.org/10.1007/bf02941833.

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48

Nazareth, S., and S. Mavinkurve. "Degradation of ferulic acid via 4-vinylguaiacol by Fusarium solani (Mart.) Sacc." Canadian Journal of Microbiology 32, no. 6 (June 1, 1986): 494–97. http://dx.doi.org/10.1139/m86-090.

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Fusarium solani (Mart.) Sacc. metabolizes ferulic acid to a transient intermediate, 4-vinylguaiacol, a compound hitherto not reported in the metabolic pathway of ferulic acid in fungi. The compound was isolated in pure form and identified spectrometrically. 4-Vinylguaiacol was further metabolized to vanillin, vanillic acid, and protocatechuic acid, followed by ortho cleavage of the aromatic ring. The organism was also found to catabolize eugenol and p-coumaric acid, but not cinnamic acid.

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Orhan, Ilkay, Murat Kartal, Yüksel Kan, and Bilge Şener. "Activity of Essential Oils and Individual Components against Acetyland Butyrylcholinesterase." Zeitschrift für Naturforschung C 63, no. 7-8 (August 1, 2008): 547–53. http://dx.doi.org/10.1515/znc-2008-7-813.

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We have tested acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities of nineteen essential oils obtained from cultivated plants, namely one from Anethum graveolens L. (organic fertilizer), two from Foeniculum vulgare Mill. collected at fullymature and flowering stages (organic fertilizer), two from Melissa officinalis L. (cultivated using organic and chemical fertilizers), two from Mentha piperita L. and M. spicata L. (organic fertilizer), two from Lavandula officinalis Chaix ex Villars (cultivated using organic and chemical fertilizers), two from Ocimum basilicum L. (green and purple-leaf varieties cultivated using only organic fertilizer), four from Origanum onites L., O. vulgare L., O. munitiflorum Hausskn., and O. majorana L. (cultivated using organic fertilizer), two from Salvia sclarea L. (organic and chemical fertilizers), one from S. officinalis L. (organic fertilizer), and one from Satureja cuneifolia Ten. (organic fertilizer) by a spectrophotometric method of Ellman using ELISA microplate-reader at 1 mg/ml concentration. In addition, a number of single components widely encountered in most of the essential oils [γ-terpinene, 4-allyl anisole, (-)-carvone, dihydrocarvone, (-)-phencone, cuminyl alcohol, cumol, 4-isopropyl benzaldehyde, trans-anethole, camphene, iso-borneol, (-)-borneol, l-bornyl acetate, 2- decanol, 2-heptanol, methyl-heptanol, farnesol, nerol, iso-pulegol, 1,8-cineole, citral, citronellal, citronellol, geraniol, linalool, α-pinene, β-pinene, piperitone, iso-menthone, menthofurane, linalyl oxide, linalyl ester, geranyl ester, carvacrol, thymol, menthol, vanilline, and eugenol] was also screened for the same activity in the same manner. Almost all of the essential oils showed a very high inhibitory activity (over 80%) against both enzymes, whereas the single components were not as active as the essential oils.

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Yemiş, Gökçe Polat, Franco Pagotto, Susan Bach, and Pascal Delaquis. "Thermal Tolerance and Survival ofCronobacter sakazakiiin Powdered Infant Formula Supplemented with Vanillin, Ethyl Vanillin, and Vanillic Acid." Journal of Food Science 77, no. 9 (August 17, 2012): M523—M527. http://dx.doi.org/10.1111/j.1750-3841.2012.02834.x.

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Journal articles on the topic 'Vanilline'

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