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1

Lương, Thị Thanh, Phương Linh Trần, Thị Ngọc Trang Vũ та ін. "CẢI TIẾN TỔNG HỢP ACID (E)-4-(PIPERIDIN-1-YL) BUT-2-ENOIC HYDROCLORID LÀM CHẤT TRUNG GIAN QUAN TRỌNG TRONG ĐIỀU CHẾ THUỐC ĐIỀU TRỊ UNG THƯ PHỔI DACOMITINIB". Tạp chí Y Dược học Cần Thơ, № 84 (25 лютого 2025): 122–28. https://doi.org/10.58490/ctump.2025i84.3295.

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Đặt vấn đề: Dacomitinib là một chất ức chế EGFR tyrosin-kinase (TKIs) được chấp thuận sử dụng vào tháng 9 năm 2018 bởi FDA và vào tháng 3 năm 2019 bởi EMA làm thuốc điều trị đầu tay cho bệnh nhân trưởng thành mắc ung thư phổi dạng không tế bào nhỏ (NSCLC). Một trong số các chất trung gian quan trọng trong quy trình tổng hợp dacomitinib là acid (E)-4-(piperidin-1yl)but-2-enoic hydroclorid (LT-03). Hiện nay có nhiều tác giả quốc tế đã công bố về phương pháp tổng hợp LT-03, chủ yếu từ nguyên liệu là dẫn chất ester của acid crotonic (các alkyl crotonat). Bài báo này công bố một phương pháp mới để
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2

Parodi, Adriano, Alexandra Jorea, Maurizio Fagnoni, et al. "Bio-based crotonic acid from polyhydroxybutyrate: synthesis and photocatalyzed hydroacylation." Green Chemistry 23, no. 9 (2021): 3420–27. http://dx.doi.org/10.1039/d1gc00421b.

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Bio-based crotonic acid was prepared via the thermolytic distillation of polyhydroxybutyrate (PHB) and PHB-enriched bacteria, and then subjected to a photocatalyzed hydroacylation, showing a comparable reactivity with that of commercial crotonic acid.
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3

Danish, Isravel A., and Karnam J. R. Prasad. "Synthesis of 5-Methyl-1,2,3,4,5,6-hexahydrocyclopenta[g]carbazole-1,7- diones and Crotonyl-2-isopropyl-1-oxo-1,2,3,4-tetrahydrocarbazoles from 1-Oxo-1,2,3,4-tetrahydrocarbazoles by Friedel-Crafts Reaction." Zeitschrift für Naturforschung B 59, no. 6 (2004): 711–15. http://dx.doi.org/10.1515/znb-2004-0613.

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The reaction of 1-oxo-1,2,3,4-tetrahydrocarbazoles (1) with crotonic acid in polyphosporic acid afforded hitherto unknown 5-methyl-1,2,3,4,5,6-hexahydrocyclopenta[g]carbazole-1,7-diones (2) and 6-crotonyl-2-isopropyl-1-oxo-1,2,3,4-tetrahydrocarbazoles (3) in a single step. A plausible mechanism for the formation of the title compounds has been proposed, and all new compounds were characterized by IR, NMR, mass spectral methods and elemental analysis.
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4

Guseinov, K. Z., M. A. Mirzoyeva, and P. A. Aliyev. "CYANALKYLATION OF MERCAPTOACETIC ACID ESTERS." Azerbaijan Chemical Journal, no. 4 (December 8, 2021): 30–34. http://dx.doi.org/10.32737/0005-2531-2021-4-30-34.

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The addition of mercaptoacetic acid esters (MAAE) to nitriles of acrylic, methacrylic, and crotonic acids easily occurs in the presence of triethylamine as a catalyst to form the corresponding 2-cyanoal-kyl¬alkoxycarbonylmethyl sulfides
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5

Liu, Xing, Entezar Mehrabi Nasab, and Seyyed Shamsadin Athari. "Anti-inflammatory effect of N-(trifluoromethylphenyl)- 2-cyano-3-hydroxy-crotonic acid amide and gluconic acid on allergic rhinitis and asthma controlling." Allergologia et Immunopathologia 50, no. 6 (2022): 71–75. http://dx.doi.org/10.15586/aei.v50i6.612.

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Allergic rhinitis and asthma are the main airway diseases with a higher prevalence. Eosinophilic inflammation, airway hyperresponsiveness, mucus hypersecretion, and reversible airflow obstruction are immunopathogenesis symptoms of rhinitis and asthma. Crotonic acid has bioactivity on the inflammation, and gluconic acid as chelator may protect crotonic acid activity in airway and together may control allergic rhinitis and asthma.Allergic rhinitis and asthma mice models were treated with crotonic and gluconic acids. The total IgE, histamine, IL-4, IL-5, and IL-13 levels were measured. In lung ti
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6

Pulat, Mehlika, and Meliha Çetin. "Pantoprazole-Na Release from Poly(acrylamide-co-crotonic acid) and Poly(acrylic acid-co-crotonic acid) Hydrogels." Journal of Bioactive and Compatible Polymers 23, no. 4 (2008): 305–18. http://dx.doi.org/10.1177/0883911508090201.

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7

Helavi, V. B., S. B. Solabannavar, R. S. Salunkhe, and R. B. Mane. "Microwave-Assisted Solventless Pechmann Condensation." Journal of Chemical Research 2003, no. 5 (2003): 279–80. http://dx.doi.org/10.3184/030823403103173796.

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Solventless Pechmann condensation of various phenols with crotonic acid, malic acid, fumaric acid or maleic acid, using sulfuric acid or anhydrous zinc chloride under microwave irradiation yielded coumarins and chromanones.
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8

FURUYOSHI, Setsuo, Yoshito NAWA, and Nariyoshi KAWABATA. "Microbial production of 2-oxobutyric acid from crotonic acid." Agricultural and Biological Chemistry 55, no. 1 (1991): 123–28. http://dx.doi.org/10.1271/bbb1961.55.123.

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9

Furuyoshi, Setsuo, Yoshito Nawa, and Nariyoshi Kawabata. "Microbial Production of 2-Oxobutyric Acid from Crotonic Acid." Agricultural and Biological Chemistry 55, no. 1 (1991): 123–28. http://dx.doi.org/10.1080/00021369.1991.10870562.

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10

TSUKASA, Hidetaka. "Synthesis of Whisky Lactone from Crotonic Acid." Journal of Japan Oil Chemists' Society 36, no. 1 (1987): 51–53. http://dx.doi.org/10.5650/jos1956.36.51.

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11

Muroga, Yoshio, and Mitsuru Nagasawa. "Potentiometric Titration Behavior of Poly(crotonic acid)." Polymer Journal 18, no. 1 (1986): 15–19. http://dx.doi.org/10.1295/polymj.18.15.

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12

Ungerfeld, E. M., S. R. Rust, and R. Burnett. "Increases in microbial nitrogen production and efficiency in vitro with three inhibitors of ruminal methanogenesis." Canadian Journal of Microbiology 53, no. 4 (2007): 496–503. http://dx.doi.org/10.1139/w07-008.

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It was hypothesized that the addition of crotonic acid or 3-butenoic acid would relieve constraints in digestibility observed when methane formation is inhibited by lumazine, propynoic acid, or ethyl 2-butynoate. In six incubations, one of the three methanogenesis inhibitors, at three different concentrations, was combined with either crotonic acid or 3-butenoic acid at two different concentrations. A mixture of buffer and ruminal fluid (4:1) was incubated with grass hay in Erlenmeyer flasks for 72 h. Initial concentrations were 0, 0.6, and 1.2 mmol/L for lumazine; 0, 2, and 4 mmol/L for propy
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13

Xu, Changliang, Xiaoguang Bai, Jian Xu, et al. "Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study." RSC Advances 7, no. 8 (2017): 4763–75. http://dx.doi.org/10.1039/c6ra24953a.

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14

Hosseinzadeh, Hossein, and Darioush Alijani. "Synthesis, Characterization and Swelling Properties of Chitosan/Poly(acrylic acid-co-crotonic acid) Semi-Interpenetrating Polymer Networks." Polymer Korea 38, no. 5 (2014): 588–95. http://dx.doi.org/10.7317/pk.2014.38.5.588.

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15

Esmaeili, Mehdi, Brendan Paget, and Dmitriy Soldatov. "Solid-state photoreactivity of cinnamic acid and crotonic acid compared." Acta Crystallographica Section A Foundations and Advances 77, a1 (2021): a290. http://dx.doi.org/10.1107/s0108767321097099.

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16

Farid, Nur Falia Shazana Manja, Hidayah Ariffin, Mohd Rahimi Zakaria Mamat, Mior Ahmad Khushairi Mohd Zahari, and Mohd Ali Hassan. "Non-solvent-based pretreatment of poly(3-hydroxybutyrate) for improved bio-based crotonic acid production." RSC Advances 5, no. 42 (2015): 33546–53. http://dx.doi.org/10.1039/c5ra03017j.

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17

IC, TEWARI, RAJESH SHUKLA, and SUSHMA RANI. "OXIDATION OF CROTONIC ACID WITH CE (IV) PERCHLORATES." International Journal of Chemical Research 4, no. 1 (2012): 122–25. http://dx.doi.org/10.9735/0975-3699.4.1.122-125.

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18

Khachatryan, H. N. "Aza-Michael addition of pyrazoles to crotonic acid." Russian Journal of General Chemistry 87, no. 3 (2017): 572–74. http://dx.doi.org/10.1134/s1070363217030318.

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19

Li-Mei, Fan, Liu Chun-Yu, Ma Zhi-Wei, Sun Cheng-Lin, and Zhou Mi. "High pressure Raman investigations on crystalline crotonic acid." Optik 127, no. 5 (2016): 3112–16. http://dx.doi.org/10.1016/j.ijleo.2015.11.209.

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20

Hack, Ellen, Dominik Hümmer, and Matthias Franzreb. "Concentration of crotonic acid using capacitive deionization technology." Separation and Purification Technology 209 (January 2019): 658–65. http://dx.doi.org/10.1016/j.seppur.2018.08.049.

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21

Galust'yan, G. G. "Homolytic addition of cyclic ethers to crotonic acid." Chemistry of Heterocyclic Compounds 35, no. 1 (1999): 33–36. http://dx.doi.org/10.1007/bf02251657.

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22

Rivera Tito, Harry Anderson, Gerardo Hernández-Sosa, Carlos Romero-Nieto, et al. "Extraction of 2′-O-apiosyl-6′-O-crotonic acid-betanin from the ayrampo seed (Opuntia soehrensii) cuticle and its use as an emitting layer in an organic light-emitting diode." RSC Advances 10, no. 60 (2020): 36695–703. http://dx.doi.org/10.1039/d0ra05543c.

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23

Samorì, Chiara, Alisar Kiwan, Cristian Torri, Roberto Conti, Paola Galletti, and Emilio Tagliavini. "Polyhydroxyalkanoates and Crotonic Acid from Anaerobically Digested Sewage Sludge." ACS Sustainable Chemistry & Engineering 7, no. 12 (2019): 10266–73. http://dx.doi.org/10.1021/acssuschemeng.8b06615.

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24

Yue, Chuan-Jun, Huang-Li Chen, Li-Ping Gu, Ji-Wei Zheng, and Ya-Feng Zhuang. "Synthesis of crotonic acid from ethanol by sequential catalysis." Sustainable Chemistry and Pharmacy 17 (September 2020): 100288. http://dx.doi.org/10.1016/j.scp.2020.100288.

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25

Kang, Shimin, and Jian Yu. "Reaction routes in catalytic reforming of poly(3-hydroxybutyrate) into renewable hydrocarbon oil." RSC Advances 5, no. 38 (2015): 30005–13. http://dx.doi.org/10.1039/c5ra03195h.

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Crotonic acid is a major monomeric intermediate in the H<sub>3</sub>PO<sub>4</sub> catalytic poly(3-hydroxybutyrate) decomposition. Propylene and 2,3-dimethyl-2-cyclopenten-1-one are two key intermediates for formation of the main aromatic products.
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26

Boyakhchyan, M. G., V. E. Badalyan, E. B. Safaryan, N. I. Asatryan, and P. S. Voskanyan. "Production of a Vinyl Acetate–Vinyl Pyrrolidone–Crotonic Acid Terpolymer." International Polymer Science and Technology 34, no. 9 (2007): 29–32. http://dx.doi.org/10.1177/0307174x0703400904.

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27

Galust'yan, G. G. "ChemInform Abstract: Homolytic Addition of Cyclic Ethers to Crotonic Acid." ChemInform 31, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.200001052.

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28

Zhang, Youquan, Aimin Yu, Jiru Jia, et al. "NaH promoted [4+3] annulation of crotonate-derived sulfur ylides with thioaurones: synthesis of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines." Chemical Communications 53, no. 77 (2017): 10672–75. http://dx.doi.org/10.1039/c7cc04466f.

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The [4+3] annulation reaction of crotonic acid derivative sulfur ylides with thioaurones has, for the first time, been reported using NaH as the base. A diverse array of 2,5-dihydrobenzo[4,5]thieno[3,2-b]oxepines is obtained in good to excellent yields. The proposed mechanism is investigated and supported by DFT calculations.
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29

Mohammed, Rasha A., and Hazim A. Walli. "Removal of Cr (III) by using Chitosan-Grafting-Poly(Acryl Acid-Crotonic Acid) Characterization and Kinetic Study." INTERNATIONAL JOURNAL OF PHARMACEUTICAL QUALITY ASSURANCE 14, no. 03 (2023): 671–74. http://dx.doi.org/10.25258/ijpqa.14.3.35.

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Hydrogel nanocomposites were prepared using free radical polymerization chitosan and acrylic acid (AA) in combination with crotonic acid. KPS was employed as the initiating agent, while MBA functioned as the cross-linking agent. The nanocomposite of Ch-g-P(AA-co-CA) is a powerful pollutant absorber. Cr (III) was removed from the water using the combination. Field emission scanning electron microscopy (FESEM) and infrared spectroscopy (FTIR) were used to examine the nanocomposites’ structure and morphology. The kinetics of Cr (III) adsorption was studied using these rates. Pseudo-second order k
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30

Sanjeeva Reddy, Ch. "Homogeneous catalysis of manganese(II) in acid bromate oxidation of olefinic acids." Collection of Czechoslovak Chemical Communications 53, no. 12 (1988): 3138–48. http://dx.doi.org/10.1135/cccc19883138.

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Manganese(II)-catalysed acid bromate oxidation of acrylic trans-crotonic and trans-cinnamic acids, in the presence of mercury(II), a bromide ion scavenger, exhibits first order in concentration of bromate, and reaches an upper limit with increase in substrate as well as catalyst concentration. Oxidation rate increases with acidity and is not altered when deuterium replaces either α or β proton of the olefinic acid. The catalytic effect of Mn(II) is displayed by its complex forming ability and the proposed mechanism assumes the oxidation of the formed Mn(II)-substrate π complex to Mn(III)-subst
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31

Karadağ, Erdener, Ömer Bariş Üzüm, and Dursun Saraydin. "Water uptake in chemically crosslinked poly(acrylamide-co-crotonic acid) hydrogels." Materials & Design 26, no. 4 (2005): 265–70. http://dx.doi.org/10.1016/j.matdes.2004.07.014.

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32

Fausto, Rui. "An infrared and raman spectroscopic study of crystalline trans-crotonic acid." Journal of Molecular Structure: THEOCHEM 377, no. 2 (1996): 181–92. http://dx.doi.org/10.1016/s0166-1280(96)91073-8.

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33

Yiamsawas, Doungporn, Wiyong Kangwansupamonkon, Orawon Chailapakul, and Suda Kiatkamjornwong. "Synthesis and swelling properties of poly[acrylamide-co-(crotonic acid)] superabsorbents." Reactive and Functional Polymers 67, no. 10 (2007): 865–82. http://dx.doi.org/10.1016/j.reactfunctpolym.2007.05.011.

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34

Wang, Lei, Zhen Zong, Yuanlin Liu, et al. "Metabolic engineering of Yarrowia lipolytica for the biosynthesis of crotonic acid." Bioresource Technology 287 (September 2019): 121484. http://dx.doi.org/10.1016/j.biortech.2019.121484.

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35

Fausto, Rui. "An infrared and raman spectroscopic study of crystalline trans-crotonic acid." Journal of Molecular Structure 377, no. 2 (1996): 181–92. http://dx.doi.org/10.1016/0022-2860(95)09119-x.

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36

Solovskii, M. V. "Synthesis of modified N-vinylpyrrolidone-crotonic acid-p-nitrophenyl crotonate terpolymer." Russian Journal of Applied Chemistry 79, no. 7 (2006): 1143–45. http://dx.doi.org/10.1134/s1070427206070196.

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37

Saraydin, Dursun, Erdener Karadağ, and Olgun Güven. "The releases of agrochemicals from radiation induced acrylamide/crotonic acid hydrogels." Polymer Bulletin 41, no. 5 (1998): 577–84. http://dx.doi.org/10.1007/s002890050404.

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38

Jyoti Chaudhary. "Synthesis, Characterization and Curing of Vinyl ester resin." Journal of Environmental Nanotechnology 2, (Special Issue) (2022): 42–45. http://dx.doi.org/10.13074/jent.2013.02.nciset37.

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The epoxy resin employed in this study is synthesized by using excess of epichlorohydrin and aniline. Further the prepared diglycidyl aniline epoxy resin (DGA) is treated by crotonic acid to form vinyl ester resin (VER).The resultant resin was characterized by FT-IR spectral studies. The curing study of this resin was monitored by Differential Scanning Calorimeter (DSC). The unreinforced cured resin was subjected to Thermogravimetric analysis (TGA).
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39

Allan, J. R., J. G. Bonner, H. J. Bowley, D. L. Gerrard, and S. Hoey. "Thermal studies on fumaric acid and crotonic acid compounds of Cobalt(II) and Nickel(II)." Thermochimica Acta 141 (March 1989): 227–33. http://dx.doi.org/10.1016/0040-6031(89)87057-1.

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40

Pulat, Mehlika, and Do?an Babayi?it. "Graft copolymerization of PU membranes with acrylic acid and crotonic acid using benzoyl peroxide initiator." Journal of Applied Polymer Science 80, no. 14 (2001): 2690–95. http://dx.doi.org/10.1002/app.1383.

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41

Sargsyan, S. H., K. S. Margaryan, and A. S. Sargsyan. "Metal-Containing Nanocomposites Based on 1-Vinyl-1,2,4-triazole–Crotonic Acid Copolymer." Russian Journal of Applied Chemistry 91, no. 2 (2018): 310–13. http://dx.doi.org/10.1134/s1070427218020210.

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42

NARUCHI, Kiyoshi, Fumihiko AKUTSU, Tsutomu AYUHA, and Masatoshi MIURA. "Copolymerization of anhydrides and dimethyl esters of crotonic acid dimer with acrylonitrile." KOBUNSHI RONBUNSHU 46, no. 3 (1989): 183–88. http://dx.doi.org/10.1295/koron.46.183.

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43

Jasicka-Misiak, Izabela, Piotr P. Wieczorek, and Paweł Kafarski. "Crotonic acid as a bioactive factor in carrot seeds (Daucus carota L.)." Phytochemistry 66, no. 12 (2005): 1485–91. http://dx.doi.org/10.1016/j.phytochem.2005.04.005.

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44

Zhang, Chan, Qiang Li, Ling Zhan, Xiao-Lou Wang, Jia-Jia Zhang, and Chao-Jin Xu. "Inactivation of horseradish peroxidase with crotonic acid for reprobing of western blotting." Analytical Biochemistry 665 (March 2023): 115070. http://dx.doi.org/10.1016/j.ab.2023.115070.

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45

Saraydın, Dursun, Ebru Şahin Yıldırım, Erdener Karadağ, and Olgun Güven. "Radiation-Synthesized Acrylamide/Crotonic Acid Hydrogels for Selective Mercury (II) Ion Adsorption." Advances in Polymer Technology 37, no. 3 (2016): 822–29. http://dx.doi.org/10.1002/adv.21725.

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46

Shapekova, N. L., and R. Z. Safarov. "In silico analysis of anticancer effects of anabasine derivatives." BULLETIN of the L.N. Gumilyov Eurasian National University. BIOSCIENCE Series 134, no. 1 (2021): 6–19. http://dx.doi.org/10.32523/2616-7034-2021-134-1-6-19.

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In the paper a review of using of different derivatives of anabasine is represented. As well results of computer QSAR investigations of N-(anabazinil)-isobutyric acid, N-(anabazinil)- isovaleric acid, N-(anabazinil)-trimethylacetic acid, N-(anabazinil)-crotonic acid, N-(anabazinil)- chloroacetic acid are represented. For in silico analysis PASS, Molinspiration, OSIRIS software has been used. The results obtained show that summarizing all predictions N-(anabazinil)- isobutyric acid and N-(anabazinil)-chloroacetic acid are acceptable structures for creation new more active and effective derivati
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47

Salazar Avalos, Arturo, Minna Hakkarainen, and Karin Odelius. "Superiorly Plasticized PVC/PBSA Blends through Crotonic and Acrylic Acid Functionalization of PVC." Polymers 9, no. 12 (2017): 84. http://dx.doi.org/10.3390/polym9030084.

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48

Naruchi, Kiyoshi, and Masatoshi Miura. "Thermal dimerization of alkali-metal salts of crotonic acid in the solid state." Journal of the Chemical Society, Perkin Transactions 2, no. 2 (1987): 113. http://dx.doi.org/10.1039/p29870000113.

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49

Sun, Wen-Jun, Peter Salmon, James Wilson, and Neal Connors. "Crotonic acid-directed biosynthesis of the immunosuppressants produced by Streptomyces hygroscopicus var. ascomyceticus." Journal of Fermentation and Bioengineering 86, no. 3 (1998): 261–65. http://dx.doi.org/10.1016/s0922-338x(98)80003-2.

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50

Solovskii, M. V., M. S. Borisenko, E. B. Tarabukina, and A. I. Amirova. "Synthesis of Copolymers of N-Vinylpyrrolidone with Crotonic Acid Modified with 4-Oxybenzaldehyde." Russian Journal of General Chemistry 88, no. 3 (2018): 514–19. http://dx.doi.org/10.1134/s1070363218030192.

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