28343-22-8Relevant academic research and scientific papers
Isolation and identification of a potent radical scavenger (canolol) from roasted high erucic mustard seed oil from nepal and its formation during roasting
Shrestha, Kshitij,Stevens, Christian V.,De Meulenaer, Bruno
, p. 7506 - 7512 (2012)
Roasting of high erucic mustard (HEM) seed has been reported to give a typical flavor and increase the oxidative stability of the extracted oil. A potent radical scavenging compound was successfully isolated from roasted HEM seed oil in a single-step chromatographic separation using an amino solid-phase extraction column. Nuclear magnetic resonance and mass spectrometry spectra revealed the compound as 2,6-dimethoxy-4-vinylphenol (generally known as canolol), and its identity was fully confirmed by chemical synthesis. The formation of canolol during roasting was compared among HEM varieties (Brassica juncea, B. juncea var. oriental, Brassica nigra, and Sinapis alba) together with a low erucic rapeseed variety. HEM varieties were shown to produce less than one-third of canolol compared to rapeseed at similar roasting conditions. This observation was linked to a lower free sinapic acid content together with a lower loss of sinapic acid derivatives in the HEM varieties compared to rapeseed. Around 50% of the canolol formed in the roasted seed was shown to be extracted in the oil. Roasting of HEM seed before oil extraction was found to be a beneficial step to obtain canolol-enriched oil, which could improve the oxidative stability.
Antioxidant canolol production from a renewable feedstock via an engineered decarboxylase
Morley, Krista L.,Grosse, Stephan,Leisch, Hannes,Lau, Peter C. K.
, p. 3312 - 3317 (2013)
Canolol (4-vinylsyringol, VS), a potent antioxidant and an alkylperoxyl radical scavenger originally discovered in crude canola oil (rapeseed), is produced by decarboxylation of sinapic acid (SA) during canola seed roasting. Chemical syntheses of VS from SA require thermal or microwave induced decarboxylation in the presence of a base. A laboratory-evolved enzyme, designated SA decarboxylase (SAD), was developed in this study. In a biphasic bioreactor system, SAD was shown to produce VS from SA extracts prepared from canola meal with an overall yield of 3.0 mg VS per g of canola meal. In addition, we investigated the application of VS in polymerization to produce polyvinylsyringol (PVS) as a potential biodegradable polymer. The characteristics of PVS determined by thermogravimetric analysis, differential scanning calorimetry and nanoindentation tests are described.
Production of canolol from canola meal phenolics via hydrolysis and microwave-induced decarboxylation
Khattab, Rabie Y.,Eskin, Michael N.A.,Thiyam-Hollander, Usha
, p. 89 - 97 (2014)
A potent antioxidant, anti-inflammatory and anti-mutagenic agent; 4-vinyl-2,6-dimethoxyphenol (canolol) was obtained from canola meal in a significant yield via alkaline (NaOH)/enzymatic (ferulic acid esterase) hydrolysis followed by microwave-assisted decarboxylation. The hydrolysis was carried out either through using canola meal directly as a substrate or by using the 70 % aqueous methanolic extract filtrates. The hydrolyzed extracts underwent RP-HPLC analysis which showed that 81.0 and 94.8 % of the total phenolics were hydrolyzed to sinapic acid after the alkaline hydrolysis of the meal and the methanolic extracts, respectively. The enzymatic hydrolysis showed lower conversion rates (49.5 and 58.3 %). The hydrolyzed extracts were consequently decarboxylated using 8-diazabicyclo[5.4.0]undec-7-ene under microwave irradiation at different conditions. The HPLC profiling of decarboxylated extracts showed that using microwave at 300 Wof microwave power for 12 min brought the highest sinapic acid conversion to canolol (58.3 %) yielding 4.2 mg canolol from each gram of canola meal suggesting that the process could be commercially economical. AOCS 2013.
Studies on the key aroma compounds in raw (unheated) and heated japanese soy sauce
Kaneko, Shu,Kumazawa, Kenji,Nishimura, Osamu
, p. 3396 - 3402 (2013)
An investigation using the aroma extract dilution analysis (AEDA) technique of the aroma concentrate from a raw Japanese soy sauce and the heated soy sauce revealed 40 key aroma compounds including 7 newly identified compounds. Among them, 5(or 2)-ethyl-4-hydroxy-2(or 5)-methyl-3(2H)-furanone and 3-hydroxy-4,5-dimethyl-2(5H)-furanone exhibited the highest flavor dilution (FD) factor of 2048, followed by 3-(methylthio)propanal, 4-ethyl-2-methoxyphenol, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone having FD factors from 128 to 512 in the raw soy sauce. Furthermore, comparative AEDAs, a quantitative analysis, and a sensory analysis demonstrated that whereas most of the key aroma compounds in the raw soy sauce were common in the heated soy sauce, some of the Strecker aldehydes and 4-vinylphenols contributed less to the raw soy sauce aroma. The model decarboxylation reactions of the phenolic acids during heating of the raw soy sauce revealed that although all reactions resulted in low yields, the hydroxycinnamic acid derivatives were much more reactive than the hydroxybenzoic acid derivatives due to the stable reaction intermediates. Besides the quantitative analyses of the soy sauces, the estimation of the reaction yields of the phenolic compounds in the heated soy sauce revealed that although only the 4-vinylphenols increased during heating of the raw soy sauce, they might not mainly be formed as decarboxylation products from the corresponding hydroxycinnamic acids but from the other proposed precursors, such as lignin, shakuchirin, and esters with arabinoxylan.
Antioxidant activity of soybean oil containing 4-vinylsyringol obtained from decarboxylated sinapic acid
Wang, Xiang-Yu,Yang, Dan,Jia, Cai-Hua,Shin, Jung-Ah,Hong, Soon Taek,Lee, Ki-Teak,Zhang, Hua,Lee, Yong-Hwa,Jang, Young-Seok
, p. 1543 - 1550,8 (2014)
4-Vinylsyringol was produced by decarboxylation from sinapic acid. To evaluate the antioxidant activity of 4-vinylsyringol, 500 ppm of 4-vinylsyringol, sinapic acid, or α-tocopherol was added to soybean oil and the oxidation processes were monitored by the peroxide value (PV), the thiobarbituric acid reactive substances value (TBARS) assay, and 1H-NMR spectroscopy. The results obtained by PV and TBARS indicated that soybean oil containing 4-vinylsyringol (SBO-VS) showed the highest oxidative stability. 1H-NMR analysis also showed concurring results. After 19 days of oxidation, the degradation rates of linoleic acid (4.2 %) and linolenic acid (4.4 %) in SBO-VS were significantly lower than those in other oils. Secondary oxidation products (i.e. aldehydes) were undetectable in SBO-VS by 1H NMR, whereas concentrations of such compounds in soybean oils containing α-tocopherol or sinapic acid were 38.0 ± 0.4 and 2.75 ± 0.2 mM oil, respectively. In addition, synergistic antioxidant effect between any two antioxidants was not observed.
Isolation, identification, and structure of a potent alkyl-peroxyl radical scavenger in crude canola oil, canolol
Wakamatsu, Daisuke,Morimura, Shigeru,Sawa, Tomohiro,Kida, Kenji,Nakai, Chiaki,Maeda, Hiroshi
, p. 1568 - 1574 (2005)
Alkylhydroperoxides in oxidized oil are undesirable components because they become alkylperoxyl radicals (ROO?) in the presence of heme, hemoglobin, or myoglobin in red meat. ROO? are biochemically reactive and damage nucleic acids and proteins, thereby harming living cells. We isolated a component, a highly potent ROO? scavenger, from crude canola oil (rapeseed), which we designated canolol, and identified its chemical structure, 4-vinyl-2,6-dimethoxyphenol. The canolol content of crude canola oil greatly increased after the seed was roasted as compared with that from unroasted seed, but it decreased in highly purified oil. This anti-ROO? activity was highest in crude oil, deceased after each refining step, and was lowest in highly purified refined oil. Canolol was thus generated during roasting. As shown previously, canolol is one of the most potent anti-ROO? components in crude canola oil and its potency is much greater than that of well-known antioxidants, including α-tocopherol, vitamin C, β-carotene, rutin, and quercetin.
New hybrids based on curcumin and resveratrol: Synthesis, cytotoxicity and antiproliferative activity against colorectal cancer cells
Cardona-G, Wilson,Hernández, Cristian,Herrera-R, Angie,Moreno, Gustavo
, (2021)
We synthesized twelve hybrids based on curcumin and resveratrol, and their structures were elucidated by spectroscopic analysis. The chemopreventive potential of these compounds was evaluated against SW480 human colon adenocarcinoma cells, its metastatic derivative SW620, along with the non-malignant CHO-K1 cell line. Among the tested compounds, hybrids 3e and 3i (for SW480) and 3a, 3e and 3k (for SW620) displayed the best cytotoxic activity with IC50 values ranging from 11.52 ± 2.78 to 29.33 ± 4.73 μM for both cell lines, with selectivity indices (SI) higher than 1, after 48 h of treatment. Selectivity indices were even higher than those reported for the reference drug, 5-fluorouracil (SI = 0.96), the starting compound resveratrol (SI = 0.45) and the equimolar mixture of curcumin plus resveratrol (SI = 0.77). The previous hybrids showed good antiproliferative activity.
A kinetic approach in the evaluation of radical-scavenging efficiency of sinapic acid and its derivatives
Niciforovi?, Neda,Polak, Toma?,Makuc, Damjan,Ulrih, Nata?a Poklar,Abramovic, Helena,McPhee, Derek J.
, (2017)
A kinetic approach was used to determine the radical scavenging activities of sinapic acid and its derivatives: sinapine, 4-vinylsyringol, syringic acid, syringaldehyde, and ethyl, propyl and butyl sinapate. The responses were expressed as rates of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) scavenging (RS), superoxide radical (O2-) scavenging (RFF), and β-carotene bleaching in the emulsion system (RB). For RS and RB, the esters of sinapic acid showed the highest responses while, for RFF, this was seen for syringic acid. The effectiveness of the selected compounds for scavenging these free radicals was also determined at a fixed endpoint. The early response parameters were demonstrated to be good discriminators in assessing differences for antioxidants with comparable fixed endpoint activity. The primary feature that ranks the kinetic data and the endpoint determinations is interpreted in terms of the mechanisms of the reactions involved in each of the assays conducted.
Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins
Yang, Biao,Dong, Kui,Li, Xiang-Sheng,Wu, Li-Zhu,Liu, Qiang
supporting information, p. 2040 - 2044 (2022/03/17)
An environmentally friendly and highly diastereoselective method for synthesizing indanes has been developed via a metastable-state photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water is the only byproduct.
Amino Group Functionalized Hf-Based Metal-Organic Framework for Knoevenagel-Doebner Condensation
Das, Aniruddha,Anbu, Nagaraj,Gogoi, Chiranjib,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
, p. 3396 - 3403 (2021/08/20)
A Hf(IV) metal-organic framework (MOF) with di-amino functionalized linker was obtained as a crystalline solid with UiO-67 topology under solvothermal reaction conditions. The guest free form of Hf(IV) MOF (1′) was efficiently employed as a heterogeneous catalyst to synthesize cinnamic acid derivatives via Knoevenagel-Doebner reaction for the first time. The catalyst (1′) was efficiently active to directly achieve cinnamic acid from benzaldehyde and malonic acid. The solid retained its activity up to 6th cycle with no decay in its activity. The noticeable advantages of the catalyst are its milder reaction conditions, high yield, high stability, recyclable nature towards catalysis and wide substrate scope as well as shape-selective behaviour. The possible mechanism of the reaction was also studied thoroughly with suitable control experiments.
