rutin solubility in methanol

Results obtained for the rutin raw drug powder also proved physical stability. The measurement was performed in both conductivity-adjusted water (50 S/cm with NaCl solution and pH of 5.5) and original dispersion medium. Solubility System: Sodium formate with Methanol Components: (1) Methanol; CH4O; [67-56-1] NIST Chemistry WebBook for detail (2) Sodium formate; NaCHO2; [141-53-7] NIST Chemistry WebBook for detail Original Measurements: Henstock, H., J. Chem. 0000001461 00000 n 0000234140 00000 n We use cookies on our website to ensure you get the best experience. Rutin nanocrystals were further incorporated into hydroxypropyl cellulose (HPC) gel and its long-term stability was assessed. BK2008003, the Research Program of State Key Laboratory of Food Science and Technology, Jiangnan University. Choi, A.S.; Bea, I.Y. D.S.-N.: data curation, formal analysis. Although the investigated products cannot be named directly, their official retail prices and active compounds can be mentioned, categorized and published. Samples were analyzed undiluted to increase the probability of finding even a few large particles or aggregates. 0000059935 00000 n You are accessing a machine-readable page. The FAST indexA highly sensitive indicator of the heat impact on infant formula model. 0000208810 00000 n [, The profile and content of phenolic acids and flavonoids were analyzed according to the method described by Je et al. Yltrak, S.; Kocadali, T.; elik, E.E. articles published under an open access Creative Common CC BY license, any part of the article may be reused without WebMeasuring solubility of flavonoids has already been done in several solvents, usually in water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, ethyl acetate and Delgado-Andrade, C.; Conde-Aguilera, J.A. 2016; 3(1):9. Due to their size in the nano-dimension, nanocrystals possess higher kinetic saturation solubility, and, in combination with the large surface, it leads to fast dissolution. [. In organized media of the cationic surfactant miramistin and the polymers polyvinylpyrrolidone and human serum albumin, the solubility of natural flavonoids quercetin and rutin increased by one or two orders of magnitude. With the formula .mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}CH3ONa, it is a white solid, which is formed by the deprotonation of methanol. 0000190164 00000 n Methanol has density 0.792. W.W.: data curation, formal analysis, writingoriginal draft. In this study, the effects of 17 polysaccharides found in TCMs, on the water-solubility and stability (pH 9/90C) of eight flavonoids were investigated. Microwave Accelerated Transglycosylation of Rutin by Cyclodextrin Glucanotransferase from Bacillus sp. As a result, the time required to complete the reaction decreased from dozens of hours to only several minutes (, The shortening of time-course for rutin transglycosylation using MAR technique indicates a positive effect on the enzymatic reaction. most exciting work published in the various research areas of the journal. The concentration of rutin was analyzed using high-performance liquid chromatography (, Rutin concentrations were determined using a Kroma System 2000 version 1.7 (Kontron Instruments GmbH, Augsburg, Germany) combined with a solvent delivery pump equipped (Kontron Instruments SpA, Milano, Italy) consisted of a 20 L loop, an auto sampler model 560 and an UV detector model 430 measuring at a wavelength of 255 nm. No special Author to whom correspondence should be addressed. 2011 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. For more information, please refer to After the transglycosylation of rutin, samples were filtered through 0.45 m membrane and analyzed by HPLC using Agilent ZORBAX Eclipse XDB-C18 column (4.5 mm 150 mm, 5 m). Oniszczuk, A.; Kasprzak, K.; Wjtowicz, A.; Oniszczuk, T.; Olech, M. The Impact of Processing Parameters on the Content of Phenolic Compounds in New Gluten-Free Precooked Buckwheat Pasta. Assume the kH of O2 is 1.30 103 mol/ (L atm). ; Feferman, I.H.S. ; Kanmaz, E.O. The solid hydrolyzes in water to give methanol and sodium hydroxide. Review of nonenzymatic browning and antioxidant capacity in processed foods. Indeed, samples of sodium methoxide are often contaminated with sodium hydroxide, which is difficult to detect. 0000002748 00000 n Chemically its name is quercetin-3-rutinoside, and it is sparingly soluble in water but freely soluble in methanol. Li, Y.; Kong, F. Simulating human gastrointestinal motility in dynamic in vitro models. A rapid 1, 2-hydroxylation of alkenes using a lipase and hydrogen peroxide under microwave conditions. Therefore, the mechanistic principle should be transferable to other poorly soluble antioxidants. The clinical relevance of maintaining the functional integrity of the stratum corneum in both healthy and disease-affected skin. The solubilities of benzoic acid and its nitrated derivatives (3-nitrobenzoic acid and 3,5-dinitrobenzoic acid) in seven pure solventswater, methanol, ethanol, acetonitrile, dichloromethane, toluene, and ethyl acetatewere determined experimentally over a temperature range from 273.15 K to 323.15 K under 101.3 kPa. For this purpose, a novel Please let us know what you think of our products and services. Paper should be a substantial original Article that involves several techniques or approaches, provides an outlook for 1996-2023 MDPI (Basel, Switzerland) unless otherwise stated. This work was supported by grants from the Natural Science Foundation of Jiangsu Province, Project No. Please check Chemical Book where you can find all such relevant information for solubility of most compounds that are commercially available. For e 6: 3786-3796. For more information, please refer to We use cookies on our website to ensure you get the best experience. In order to be human-readable, please install an RSS reader. The pretreatment was carried out to reduce microbial populations existing on buckwheat flours before inoculated fermentation since they would compete with and inhibit the growth of inoculated microbes during the fermentation process. The influence of microwave irradiation on lipase catalyzed kinetic resolution of racemic secondary alcohols. 1: 9. In order to optimize the transglycosylation of rutin under microwave irradiation conditions, the ratio of maltodextrin to rutin, as well as the reaction pH and temperature were also investigated. All of the polysaccharides were able to The results were positive and inspiring: Microwave irradiation could drastically accelerate the transglycosylation rate of rutin. Bachu, P; Gibson, JS; Sperry, J; Brimble, MA. Tempe fermentation is one example of the traditional way of processing soybeans into tempeh products, originating in Indonesia. In this work we emphasize rutin, quercetin glucoside, and quercetin rhamnoside which is a flavonoid that has a significant antioxidant activity with important tissue protection capacity . A PB value higher than one indicates high bioaccessibility and a PB value lower than one indicates low bioaccessibility. 207671-50-9 Purity & Quality Control Biological Activity Description Rutin (Quercetin-3-O-rutinoside, Rutoside, Sophorin) is a glycoside found in a wide variety of plants including citrus fruit. Santos, S.X.D. Molecules 2023, 28, 2746. Arsenic : Not more than 1. : data curation, formal analysis. Title: 363-400[appendices].p65 Author: Billh Created Date: In this work we emphasize rutin, quercetin glucoside, and quercetin rhamnoside which is a flavonoid that has a significant antioxidant activity with important tissue protection capacity . In. Rodriguez-Lopez, JN; Fenoll, LG; Tudela, J; Devece, C; Sanchez-Hernandez, D; de Los eyes, E; Garcia-Canovas, F. Thermal inactivation of mushroom polyphenoloxidase employing 2450 MHz microwave radiation. 0000159700 00000 n The solubility reported for rutin nanocrystals is 133 g/mL [, An improved penetration of rutin into the porcine ear skin is given when rutin with lower concentrations remains in the upper part of the stratum corneum (first 20%) and in contrast penetrates in the deeper layers (70% to 100%) of the stratum corneum with higher concentrations. Patented Aug. 29, 1950 UNITED STATES PATENT OFFICE METHOD OF PURIFYI NG RUTIN James E. Couch, Glenside, and J'oseph Naghski and William L. Porter, J. Mol. To improve its physicochemical properties, many methods have been investigated, including the use of CGTase to carry out enzymatic transglycosylation to obtain transglycosylated rutin with improved properties such as good water solubility [. Sodium methoxide is the simplest sodium alkoxide. "Identification and Bioaccessibility of Maillard Reaction Products and Phenolic Compounds in Buckwheat Biscuits Formulated from Flour Fermented by Rhizopus oligosporus 2710" Molecules 28, no. Tekliye, M.; Pei, X.; Dong, M. RP-HPLC determination of Furosine in fermented milk of different brands retailed in China. 0000002088 00000 n For example, the product B with the second highest DPPH inhibition of just below 70% can be purchased for 10.99 and has the same price as product H with a DPPH inhibition below 10% (. Quercetin : Not more than 1%. Visit our dedicated information section to learn more about MDPI. ; Levin, J. No difference in penetration depth was investigated between both formulations since the used 30 tapes only removed approximately 84% [, The transfer of the m-sized rutin raw drug powder into nanocrystals could distinctly increase the. For the improvement of spreading properties, glycerol 85% at 2.5% was added dropwise as well as the preserving agent euxyl. In addition, As-EE enhanced the expression levels of hyaluronic acid synthase-1 and occludin in HaCaT cells. As a result, the enzymatic transglycosylation reaction system consists of nearly half part of methanol (v/v), which might induce an inhibitory effect on CGTase activity. 0000159723 00000 n 0000001310 00000 n 0000199543 00000 n Variables: Prepared By: T. A. Ageyeva Experimental Approved Methods of the American Association of Cereal Chemists, Data expressed as mean standard deviation (, Help us to further improve by taking part in this short 5 minute survey, Investigation of Molecular Mechanism of Cobalt Porphyrin Catalyzed CO, Untargeted Metabolomic Analysis and Chemometrics to Identify Potential Marker Compounds for the Chemical Differentiation of, Isolation, Identification and Application of Biologically Active Natural Products, https://creativecommons.org/licenses/by/4.0/. To the best of our knowledge, enzymatic transglycosylation of rutin under microwave irradiation conditions has not been reported so far. Computational calculations in microwave-assisted organic synthesis (MAOS). 0000134748 00000 n For trailer << /Size 48 /Info 2 0 R /Encrypt 6 0 R /Root 5 0 R /Prev 235919 /ID[<6e4895a384002dcdac0ff3f937ee68a2>] >> startxref 0 %%EOF 5 0 obj << /Type /Catalog /Pages 1 0 R /Metadata 3 0 R >> endobj 6 0 obj << /Filter /Standard /R 2 /O ( UV.`Dz-#_m_}g) /U (mo@~M&L_\r) /P -60 /V 1 /Length 40 >> endobj 46 0 obj << /S 36 /Filter /FlateDecode /Length 47 0 R >> stream The mobile phase contained a mixture of acetonitrile, water and formic acid (18:81.9:0.1, v/v/v) and the flow rate was 0.8 mL/min. Int. Silva, A.R. Solubility System: Methanol with Toluene and Water Components: (1) Water; H2O; [7732-18-5] NIST Chemistry WebBook for detail (2) Methanol (methyl alcohol); CH4O; [67-56-1] NIST Chemistry WebBook for detail (3) Toluene (methylbenzene); C7H8; [108-88-3] NIST Chemistry WebBook for detail Evaluator: Generally, the antioxidant activities of the tested products can be categorized into three classes: I, II and III, where class I products were able to neutralize more than 80% of the DPPH radicals to DPPH-H molecules (A), class II products less than 80% but more than 20% (B, C, D, E and F) and class III, showing almost no reduction in DPPH activity and thus had no antioxidant properties (G, H, I, J and K). It showed almost the same curve progression as the nanocrystal gel. Nogueira, BM; Carretoni, C; Cruz, R; Freitas, S; Melo, PA; Costa-Felix, R; Pinto, JC; Nele, M. Microwave activation of enzymatic catalysts for biodiesel production. About 50 g of each type of flour was suspended with 950 mL of distilled water. 2011; 12(6):3786-3796. https://doi.org/10.3390/cosmetics3010009, Pyo, Sung Min, Martina Meinke, Cornelia M. Keck, and Rainer H. Mller. The release of glycosyl residues from the substrate (maltodextrin) for transglycosylation is dependent on the availability of a particular energy level inside the microwave oven. Zhang, Y.; Li, Y.; Ren, X.; Zhang, X.; Wu, Z.; Liu, L. The positive correlation of antioxidant activity and prebiotic effect about oat phenolic compounds. In the enzymatic transglycosylation of rutin, methanol used as solvent causes an inhibition of CGTase activities, which might result in dozens of hours of reaction time to achieve the highest conversion rate of rutin and yield of transglycosylated products, which are mono-, di-, tri-, tetra-, penta-glucosylated rutins when maltodextrin is used as the donor of glycosyl residues. Commonly, in the marketed dermal formulations, the active rutin is either dissolved in very low concentrations or dispersed as raw drug powder. Al Shaal, L.; Mller, R.H.; Shegokar, R. smartCrystal combination technologyScale up from lab to pilot scale and long term stability. Shiosaka, M; Bunya, H. Thermostable cyclodextrin forming enzyme. H.Z. : conceptualization, funding acquisition, methodology, project administration, supervision, writingoriginal draft, writingreview and editing. 0000184746 00000 n WebLithium hydroxide is an inorganic compound with the formula LiOH. 0000184723 00000 n * Refer to Certificate of Analysis for lot specific data (including water content). https://doi.org/10.3390/cosmetics3010009, Subscribe to receive issue release notifications and newsletters from MDPI journals, You can make submissions to other journals. Thus, it was complemented. Firstly, it is well known that different enzymatic reactions would require also different reaction time periods if the highest yield of products is targeted. 2016 by the authors; licensee MDPI, Basel, Switzerland. MDPI and/or Rutin is a well-known antioxidant from the group of flavonoids. However, rutin is hardly soluble in water and not very stable, which limits its practical application in industries. WebIllustrations of solubility concepts: metabolic intermediates, lipid bilayer membranes, soaps and detergents. https://doi.org/10.3390/ijms12063786, Subscribe to receive issue release notifications and newsletters from MDPI journals, You can make submissions to other journals. Sci. 0000001240 00000 n While classified as a strong base, lithium hydroxide is the weakest known alkali metal hydroxide. WebA detailed solubility study on anhydrous rutin was performed by Zi et al. You seem to have javascript disabled. those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). 0000134771 00000 n Starzyska-Janiszewska, A.; Duliski, R.; Stodolak, B.; Mickowska, B.; Wikiera, A. 0000003478 00000 n No special This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). Overall data show that the two studied extracting mixtures do not have different specificities for phenolic compounds but differ in the extraction yield. and finally cooled to 37 C. As dispersion medium purified water was used. WebThe LogS of many substances already approved for use in therapeutics have a value greater than 4.00; in this study the compounds showed a value between 0.68 and 3.44, and the compounds 1, 2, 3, and 4 were considered soluble, while compounds 5 and 6 were considered moderately soluble. 0000005010 00000 n [3], The structure, and hence the basicity, of sodium methoxide in solution depends on the solvent. Rutin was subjected to intermolecular transglycosylation assisted with microwave irradiation using cyclodextrin glucanotransferase (CGTase) produced from, Rutin is one kind of bioflavonoid, which is used as a nutritive element or an antioxidant in the cosmetic, food and beverage industries. Rutin is one kind of bioflavonoid, which is used as a nutritive element or an antioxidant in the cosmetic, food and beverage industries. Cosmetics 2016, 3, 9. 2). Purity of rutin was confirmed by ultra-performance liquid chromatography at 97.6%; yield of the purified rutin was determined to be 78.2%. 1B ), which greatly improved its water solubility (by at least 200-fold). The solubilities of rutin in water, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, acetone, and ethyl acetate were determined at T= 283.15, 298.15, 313.15, ; Gkmen, V. Effects of sprouting and fermentation on the formation of Maillard reaction products in different cereals heated as wholemeal. permission is required to reuse all or part of the article published by MDPI, including figures and tables. Verardo, V.; Arrez-Romn, D.; Segura-Carretero, A.; Marconi, E.; Fernndez-Gutirrez, A.; Caboni, M.F. 0000001683 00000 n One of the well-known advantages of nanocrystals is the increased saturation solubility and increased dissolution velocity of actives. Using 60 W at 40 C in microwave-assisted reaction (MAR) system, the transglycosylation of rutin completed within only 6 min. Sarma, K; Borthakur, N; Goswami, A. Microwave irradiation has become an effective tool in synthetic organic chemistry, dramatically increasing reaction rates and yields [, Since the time-course of rutin transglycosylation was extremely long (dozens of hours), a microwave-assisted reaction (MAR) technique was investigated in this study. Patosz, N.; Sawicki, T.; Wiczkowski, W. Profile of phenolic acids and flavonoids of red beet and its fermentation products. You can use ethanol to dissolve rutin. All authors conceived and designed the experiments; Sung Min Pyo performed the experiments and analyzed the data; after result discussion with all co-authors, Sung Min Pyo wrote the paper, which was finally reviewed by all co-authors. ; Martnez- Avila, G.; Montaez- Saenz, J.; Aguilar, C.N. Commercial batches of sodium methoxide show variable levels of degradation, and were a major source of irreproducibility when used in Suzuki reactions.[8]. Editors select a small number of articles recently published in the journal that they believe will be particularly The present study focused on comparing the transglycosylation rate of rutin under conventional conditions with that assisted with microwave irradiation using CGTase as a biocatalyst produced from, Transglycosylation is an important process for structural modification of molecules to enhance their solubility and biological properties, which can also improve their properties and action in the body system [. https://doi.org/10.3390/molecules28062746, Subscribe to receive issue release notifications and newsletters from MDPI journals, You can make submissions to other journals. In order to increase rutin saturation solubility and improve the diffusion to the skin, rutin nanocrystals were produced by the smartCrystal process, e.g., bead milling followed by high pressure homogenization. ( 25) found that the rebamipide/methanol achieved maximum solubility in 17 min, with a maximum solubility that is 3.21 times that of rebamipide. 2023; 28(6):2746. 2011. Further supporting this statement is the fact that methanol is less soluble in hexane, a nonpolar substance, than ethanol. Wronkowska, M.; Jeliski, T.; Majkowska, A.; Zieliski, H. Physical properties of buckwheat water biscuits formulated on fermented flours by selected lactic acid bacteria. It is a significantly stronger base in DMSO where it is more fully ionized and free of hydrogen bonding. For fast detection of large particles and aggregates within the formulation and for the confirmation of LD data, LM was performed with an Orthoplan Leitz (Wetzlar, Germany) at magnifications of 100, 400 and 1000. Author to whom correspondence should be addressed. See further details. WebThe LogS of many substances already approved for use in therapeutics have a value greater than 4.00; in this study the compounds showed a value between 0.68 and 3.44, and the compounds 1, 2, 3, and 4 were considered soluble, while compounds 5 and 6 were considered moderately soluble. Institute of Pharmacy, Pharmaceutics, Pharmaceutical Nanotechnology & NutriCosmetics, Kelchstr. MDPI and/or Microwave activation of enzymatic catalysis. Je, M.; Wiczkowski, W.; Zieliska, D.; Biaobrzeski, I.; Baszczak, W. The impact of high pressure processing on the phenolic profile, hydrophilic antioxidant and reducing capacity of pure obtained from commercial tomato varieties. The compound absorbs carbon dioxide from the air to form methanol and sodium carbonate, thus diminishing the alkalinity of the base. Antioxidants, free radicals and skin care. In the upper part of the stratum corneum, represented by the depths of 15%, 1.8- and 2.4-fold less relative amount of rutin could be found, where in the deeper part of the stratum corneum, represented by the depths of 80%, 4.7- and 5.4-fold increased concentrations were obtained for the rutin nanocrystal gel. S1A). ; Lee, H.G. RutinIncreased Antioxidant Activity and Skin Penetration by Nanocrystal Technology (smartCrystals). Kaneko, T; Kato, T; Nakamura, N; Horikoshi, K. Spectrophotometric determination of cyclization activity of -cyclodextrin-forming cyclomaltodextrin glucanotransferase. Microwave Accelerated Transglycosylation of Rutin by Cyclodextrin Glucanotransferase from Bacillus sp. Measurement in conductivity-adjusted water yields the Stern potential, which is proportional to the surface charge (Nernst potential) measurement in the original dispersion medium the ZP value suitable for predicting long-term stability. Solubility (25C) In vitro Chemical Information In vivo Formulation Calculator (Clear solution) Microwave irradiation accelerated dramatically the enzymatic reaction rate during rutin transglycosylation. Concretely, under specific microwave irradiation conditions, the reaction time to complete the transglycosylation of rutin decreased from dozens of hours to only several minutes. Disclaimer/Publishers Note: The statements, opinions and data contained in all publications are solely ; Teixeira, J.A. Chi et al. 0000008446 00000 n Manzocco, L.; Calligaris, S.; Mastrocola, D.; Nicoli, M.C. articles published under an open access Creative Common CC BY license, any part of the article may be reused without The authors declare no conflict of interest. Aga, H; Yoneyama, M; Sakai, S; Yamamoto, I. Synthesis of 2-O--glucopyranosyl l-ascorbic acid by cyclomaltodextrin glucanotransferase from. Predicting buckwheat flavonoids bioavailability in different food matrices under in vitro simulated human digestion. Similarly, microwave irradiation has been reported to exert positive effects on different kinds of enzymes [, Although some researchers have tried to study the effects of microwave irradiation on the structure of enzymes [, CGTase was obtained through cultivation of, After cultivation for 96 h, cells were removed by centrifugation at 10,000 rpm and 4 C for 15 min.

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