Search results for "Vanillyl"
showing 9 items of 9 documents
Multigram Scale Enzymatic Synthesis of (R)-1-(4′-Hydroxyphenyl)ethanol Using Vanillyl Alcohol Oxidase
2018
The enantioselective oxyfunctionalisation of C−H bonds is a highly interesting reaction, as it provides access to chiral alcohols that are important pharmaceutical building blocks. However, it is hard to achieve using traditional methods. One way in which it can be achieved is through the action of oxidative enzymes. Although many reports of the oxyfunctionalisation capabilities of enzymes at an analytical scale have been published, reports on the use of enzymes to achieve oxyfunctionalisation on a synthetically relevant scale are fewer. Here, we describe the scale-up of the conversion of 4-ethylphenol to (R)-1-(4′-hydroxyphenyl)ethanol using the flavin-dependent enzyme vanillyl alcohol oxi…
Tuning The Selectivity To Aldehyde Via Ph Regulation In The Photocatalytic Oxidation Of 4-Methoxybenzyl Alcohol And Vanillyl Alcohol By Tio2 Catalysts
2021
Abstract The influence of pH on the photocatalytic partial oxidation of 4-methoxybenzyl alcohol (MBA) and vanillyl alcohol (VA) to their corresponding aldehydes in aqueous suspension under UVA irradiation was investigated by using poorly crystalline home-prepared and crystalline commercial TiO2 (BDH, Merck and Degussa P25) photocatalysts. The results clearly show as tuning pH can strongly impart selectivity and activity to photocatalytic processes which are often quite unselective in aqueous suspensions. It was found that pH effect on reaction rate and product selectivity strongly depended on TiO2 crystallinity and substrate type. In the case of MBA oxidation, photoreactivity and selectivit…
Evaluation of Ligno Boost™ softwood kraft lignin epoxidation as an approach for its application in cured epoxy resins
2018
Abstract In this study, modification of LignoBoost™ softwood kraft lignin with epichlorhydrin in water-organic solvents media was realized. Lignin-based epoxy resins were obtained by two ways: acetone extraction of glycidylated lignin or glycidylation of the acetone soluble lignin fraction. The effect of glycidylation regimes on the yields of acetone soluble fractions, their functional composition and physical-chemical characteristics was investigated using wet chemistry methods, FTIR spectroscopy, size exclusion chromatography (SEC) and differential scanning calorimetry (DSC). The positive effect of the biphasic phase transfer catalytic system – KOH/quaternary ammonium salt – on glycidylat…
Vanillin Suppresses Metastatic Potential of Human Cancer Cells through PI3K Inhibition and Decreases Angiogenesis in Vivo
2009
Vanillin, a food flavoring agent, has been shown to suppress cancer cell migration and metastasis in a mouse model, but its mechanism of action is unknown. In this report, we have examined the antimetastatic potential of vanillin and its structurally related compounds, vanillic acid, vanillyl alcohol, and apocynin on hepatocyte growth factor (HGF)-induced migration of human lung cancer cells by the Transwell assay. Vanillin and apocynin could inhibit cell migration, and both compounds selectively inhibited Akt phosphorylation of HGF signaling, without affecting phosphorylation of Met and Erk. Vanillin and apocynin could inhibit the enzymatic activity of phosphoinositide 3-kinase (PI3K), as …
Dose-dependent metabolic disposition of hydroxytyrosol and formation of mercapturates in rats
2013
Hydroxytyrosol (HT), one of the major polyphenols present in olive oil, is known to possess a high antioxidant capacity. The aim of the present study was to investigate dose dependent (0, 1, 10 and 100 mg/kg) alterations in the metabolism of HT in rats since it has been reported that metabolites may contribute to biological effects. Special attention was paid to the activation of the semiquinone quinone oxidative cycle and the formation of adducts with potential deleterious effects. Thus, we developed a novel analytical methodology to monitor the in vivo formation of the HT mercapturate, N-acetyl-5-S-cysteinyl-hydroxytyrosol in urine samples. Biomarkers of hepatic and renal toxicity were ev…
Protective effect of homovanillyl alcohol on cardiovascular disease and total mortality: virgin olive oil, wine, and catechol-methylathion
2016
Background: Hydroxytyrosol is a phenolic compound that is present in virgin olive oil (VOO) and wine. Hydroxytyrosol-related foods have been shown to protect against cardiovascular disease (CVD).Objective: We investigated the associations between hydroxytyrosol and its biological metabolite, 3-O-methyl-hydroxytyrosol, also known as homovanillyl alcohol (HVAL), with CVD and total mortality.Design: We included 1851 men and women with a mean ± SD age of 66.8 ± 6 y at high risk of CVD from prospective cohort data. The primary endpoint was a composite of myocardial infarction, stroke, and death from cardiovascular causes; the secondary endpoint was all-cause mortality. Twenty-four-hour urinary h…
The effects of land abandonment and long-term afforestation practices on the organic carbon stock and lignin content of Mediterranean humid mountain …
2019
Afforestation is an important strategy that can decrease atmospheric carbon by sequestering carbon in biomass and soil. In Spain, an active afforestation programme was adopted in the 1950s when the soil was severely eroded after widespread abandonment of arable land. The Araguás catchment (Central Spanish Pyrenees) is a good example of this programme because it was afforested with both Pinus sylvestris L. (PS) and Pinus nigra J.F.Arnold (PN). The soil organic carbon (SOC) stock and lignin content (based on the vanillyl, syringyl and cinnamyl contents) of these afforested soils were examined and compared to those of bare soil, secondary succession and meadow soils. Both the SOC stock and lig…
Synthesis of vanillin in water by TiO2 photocatalysis
2012
Abstract The photoproduction of vanillin is studied in aqueous medium starting from trans-ferulic acid, isoeugenol, eugenol or vanillyl alcohol by using both commercial and home prepared TiO2 samples as photocatalysts and batch Pyrex photoreactors. The photo-oxidation at room temperature of these compounds produces vanillin with a selectivity ranging from 1.4 to 21 mol% with respect to the converted substrate. An investigation on the intermediates was performed in the case of trans-ferulic acid; for this substrate the most important intermediates were homovanillic acid, vanillyl mandelic acid, trans-caffeic acid, formic acid, acetic acid, and oxalic acid. The carbon mass balance, including …
A Hybrid Cavitand Made by Capping Permethylated α-Cyclodextrin with Cyclotriveratrylene
2012
A hybrid C 3 -symmetric cavitand 1, in which permethylated α-cyclodextrin (PM α-CDX) is capped with cyclotriveratrylene (CTV), has been prepared in 8 % yield by intramolecular cyclization of a vanillyl alcohol derivative attached to the primary rim of the CDX platform. The reaction proceeds diastereoselectively (dr ≈ 6:1), the chirality of the α-glucopyranosyl units controlling the chirality of the CTV component. Interestingly, in polar solvents, 1 shows self-complexation properties as the primary methoxy groups of the CDX component are directed towards the CTV cavity.