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Journal articles on the topic 'Enoic Acid'

Author: Grafiati

Published: 5 June 2025

Last updated: 24 June 2025

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1

Allan, RD, HW Dickenson, GAR Johnston, R. Kazlauskas, and HW Tran. "Synthesis of Analogues of GABA. XIV. Synthesis and Activity of Unsaturated Derivatives of 5-Aminopentanoic Acid (d-Aminovaleric Acid)." Australian Journal of Chemistry 38, no. 11 (1985): 1651. http://dx.doi.org/10.1071/ch9851651.

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The (Z) and (E) pairs of 5-aminopent-2-enoic acid and 5-aminopent-3- enoic acid, as well as the related 5-aminopent-3-ynoic acid, have been prepared for structure-activity studies on GABA receptors. Only the (Z) isomers were active as GABA agonists with (Z)-5-aminopent-2-enoic acid being two- to four-fold more active than 5-aminopentanoic acid.

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2

F., G. BADDAR, N. BASYOUNI M., F. EI-NEWAIRY M. та H. GHALY E. "ᵧ.ᵧ-Disubstituted Itaconic Acids. Part Vll.1 The Stobbe Condensation of Benzyl-, p-Chlorobenzyl-, and p-Methoxybenzylphenyl Ketones with Diethyl Succinate". Journal of Indian Chemical Society Vol. 51, Jul 1974 (2022): 698–704. https://doi.org/10.5281/zenodo.6417065.

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Department of <em>Chemistry, </em>Faculty of Science, A' in Shams <em>University, Cairo, Egypt.</em> <em>Manuscript received 22 October 1973 ; acepted 23 May 1974.</em> <em>\(Cis \)</em>(Ph/Ar)-5-Aryl-3-ethoxycarbonyl-4-phenyl-pent-4-enoic acids were converted into ethyl <em>\(trans\)-</em>(Ph/Ar)<em><sup>-</sup> 5-aryl-3-</em>carboxy-4-phenyl-pent-4-enoute (14), (15) and (16), which have been cyclised<em> </em>to 1-acetoxy-naphthalenes (17), (18) <em>and </em>(19). <em>\(Cis\) </em>(Ph/ Ar)<em>-4, </em>5-Diphenyl- <em>and </em>cis (Ph/Ar)-4-phenyl-5-p-tolyl-pent-4-enoic acid anhydrides<em> </em>were converted with aluminium chloride<em> </em>to<em> a </em>mixture of the corresponding cyclopentenones and arylidene tetralone carboxylic acids<em>. \(Trans \)(Ph/CO<sub>2</sub></em>E<em>t)-5-Aryl-3-</em>ethoxycarbonyl-4-phenyl-pent-3-enolc acids were cyclised to ethyl 4-acetoxY-1-arylmethyl-2-naphthoates.

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3

Zhang, Jun, Kaida Zhou, and Jie Wu. "Generation of sulfonated isobenzofuran-1(3H)-ones under photocatalysis through the insertion of sulfur dioxide." Organic Chemistry Frontiers 5, no. 5 (2018): 813–16. http://dx.doi.org/10.1039/c7qo00987a.

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Generation of sulfonated isobenzofuran-1(3H)-ones starting from 2-vinylbenzoic acids, aryldiazonium tetrafluoroborates, and DABCO˙(SO<sub>2</sub>)<sub>2</sub> under photocatalysis in the presence of visible light is achieved. Additionally, the method can be extended to 4-phenylpent-4-enoic acid and 5-phenylhex-5-enoic acid.

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4

Abou-ElWafa, Ghada S. E., Mohamed Shaaban, Khaled A. Shaaban, Mohamed E. E. El-Naggar, and Hartmut Laatsch. "Three New Unsaturated Fatty Acids from the Marine Green Alga Ulva fasciata Delile." Zeitschrift für Naturforschung B 64, no. 10 (2009): 1199–207. http://dx.doi.org/10.1515/znb-2009-1014.

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From the dichloromethane extract of the marine green alga Ulva fasciata Delile, collected from the Mediterranean coast of Egypt, three new fatty acids, namely, (E)-11-oxo-octadeca-12-enoic acid (1a), (E)-11-hydroxy-octadeca-12-enoic acid (2a) and 6-hydroxy-oct-7-enoic acid (3a) together with cholesterol were isolated. Analysis of the unpolar part of the extract using GC-MS detected the existence of further ten compounds, namely, dimethylsulfoxide, dimethylsulfone, phenylacetamide, 6,10,14-trimethyl-pentadecan-2-one, 8-heptadecene, dodecane, tridecane, 4-oxo-pentanoic acid, hexadecanoic acid, and the naturally new 1,1ʹ-bicyclohexyl. Structures of the isolated compounds 1a - 3a were confirmed by spectroscopic analyses including mass spectra (EI-MS, HR/ESIMS), 1D and 2D NMR experiments, and by the synthetic conversion into their corresponding methyl esters 1b - 3b. The algal extract and its components were comparatively examined against several pathogenic microorganisms, and brine shrimps for cytotoxicity.

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5

Teichert, Axel, Tilo Lübken, Jürgen Schmidt, Andrea Porzel, Norbert Arnold, and Ludger Wessjohann. "Unusual Bioactive 4-Oxo-2-alkenoic Fatty Acids from Hygrophorus eburneus." Zeitschrift für Naturforschung B 60, no. 1 (2005): 25–32. http://dx.doi.org/10.1515/znb-2005-0105.

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From fruit bodies of the basidiomycete Hygrophorus eburneus (Bull.: Fr.) Fr. (Tricholomataceae) eight fatty acids (C16, C18) with γ -oxocrotonate partial structure could be isolated. Initial tests demonstrate their bactericidal and fungicidal activity. The structures of (2E,9E)-4-oxooctadeca- 2,9,17-trienoic acid (1), (2E,11Z)-4-oxooctadeca-2,11,17-trienoic acid (2), (E)-4-oxohexadeca-2,15- dienoic acid (3), (E)-4-oxooctadeca-2,17-dienoic acid (4), (2E,9E)-4-oxooctadeca-2,9-dienoic acid (5), (2E,11Z)-4-oxooctadeca-2,11-dienoic acid (6), (E)-4-oxohexadec-2-enoic acid (7), and (E)-4- oxooctadec-2-enoic acid (8) were elucidated on the basis of their spectroscopic data.

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6

Sonneck, Marcel, Tim Peppel, Anke Spannenberg, and Sebastian Wohlrab. "Crystal structure of (E)-dodec-2-enoic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 7 (2015): o528—o529. http://dx.doi.org/10.1107/s2056989015011937.

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The crystal structure of (E)-dodec-2-enoic acid, C12H22O2, an α,β-unsaturated carboxylic acid with a melting point (295 K) near room temperature, is characterized by carboxylic acid inversion dimers linked by pairs of O—H...O hydrogen bonds. The carboxylic acid group and the following three carbon atoms of the chain of the (E)-dodec-2-enoic acid molecule lie almost in one plane (r.m.s. deviation for the four C atoms and two O atoms = 0.012 Å), whereas the remaining carbon atoms of the hydrocarbon chain adopt a nearly fully staggered conformation [moduli of torsion angles vary from 174.01 (13) to 179.97 (13)°].

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7

Gauthier, Kathryn M., Christina Deeter, U. Murali Krishna, et al. "14,15-Epoxyeicosa-5( Z )-enoic Acid." Circulation Research 90, no. 9 (2002): 1028–36. http://dx.doi.org/10.1161/01.res.0000018162.87285.f8.

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8

Sonneck, Marcel, Tim Peppel, Anke Spannenberg, and Sebastian Wohlrab. "Synthesis and Molecular Structures of (E)-non-2-enoic Acid and (E)-dec-2-enoic Acid." Crystals 5, no. 4 (2015): 466–74. http://dx.doi.org/10.3390/cryst5040466.

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9

FENG, Jun, Jing SHI, Sarath R. SIRIMANNE, Corinne E. MOUNIER-LEE, and Sheldon W. MAY. "Kinetic and stereochemical studies on novel inactivators of C-terminal amidation." Biochemical Journal 350, no. 2 (2000): 521–30. http://dx.doi.org/10.1042/bj3500521.

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C-terminal amidation, a required post-translational modification for the bioactivation of many neuropeptides, entails sequential enzymic action by peptidylglycine α-mono-oxygenase (PAM, EC 1.14.17.3) and peptidylamidoglycolate lyase (PGL, EC 4.3.2.5). Here we introduce novel compounds in which an olefinic functionality is incorporated into peptide analogues as the most potent turnover-dependent inactivators of PAM. Kinetic parameters for PAM inactivation by 4-oxo-5-acetamido-6-phenyl-hex-2-enoic acid and 4-oxo-5-acetamido-6-(2-thienyl)-hex-2-enoic acid were obtained by using both the conventional dilution assay method and the more complex progress curve method. The results obtained from the progress curve method establish that these compounds exhibit the kinetic characteristics of pure competitive inactivators (i.e. no ESI complex forms during inactivation). On the basis of kinact/Ki values, 4-oxo-5-acetamido-6-(2-thienyl)-hex-2-enoic acid is almost two orders of magnitude more potent than benzoylacrylate, a chemically analogous olefinic inactivator that lacks the peptide moiety. Stereochemical studies established that PAM inactivation by 4-oxo-5-acetamido-6-(2-thienyl)-hex-2-enoic acid is stereospecific with respect to the moiety at the P2 position, which is consistent with previous results with substrates and reversible inhibitors. In contrast, 2,4-dioxo-5-acetamido-6-phenylhexanoic acid, which is a competitive inhibitor with respect to ascorbate, exhibits a low degree of stereospecificity in binding to the ascorbate sites of both PAM and dopamine-β-hydroxylase.

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10

Vijender, Singh, Ali Mohammed, Malik Archana, and Sultana Shahnaz. "New aliphatic constituents from the aerial parts of Artemisia annua L." Algerian Journal of Natural Products 5, no. 2 (2017): 515–23. https://doi.org/10.5281/zenodo.1117151.

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<em>Artemisia annua</em> L. (Asteraceae) is an aromatic annual herb, up to 2 m in height, found in temperate Asia, especially China and naturalized in many countries of the world.  The plant is prescribed against fever, malaria, skin diseases, jaundice, malignant ulcers and haemorrhoids. Phytochemical investigation of the aerial parts of <em>A. annua</em> led to the isolation of alkyl alcohols, fatty acid esters, alkyl glucoside and fatty acids characterized as <em>n-</em>nonadecan-2β-ol (isononadecanol, <strong>1</strong>), <em>n-</em>docosan-9β-ol (isodocosanol, <strong> 2</strong>), 1<em>-</em>octacosanol (<em>n-</em>octacosanyl alcohol,<strong> 3</strong>), <em>n</em>-heptadecanyl <em>n</em>-octadec-9,12-dienoate (<em>n</em>-heptadecanyl linoleate, <strong> 4</strong>), <em>n</em>-octadecanyl <em>n-</em>octadec-9,12,-dienoate (<em>n</em>-octadecanyl linoleate, <strong>5</strong>), <em>n</em>-nonacosanyl <em>n</em>-octadec-9, 12-dienoate (<em>n</em>-nonacosanyl linoleate,<strong> 6</strong>), <em>n</em>-cos-(Z)-10-enoic acid (<em>cis</em>-cos-10-enoic acid, <strong>7</strong>), <em>n</em>-cos-(Z)-9-enoic acid (<em>cis-c</em>os-9-enoic acid<strong>, 8</strong>) and <em>n-</em>heptadecanyl-ß-D-glucopyronoside (<em>n</em>-heptadecanyl glucoside,<strong> 9</strong>). The structures of all phytoconstituents, isolated for the first time from <em>A. annua</em> have been elucidated on the basis of spectral data analysis and chemical reactions

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11

Ciesielski, Wojciech, Henryk Kołoczek, Zdzisław Oszczęda, Jacek A. Soroka, and Piotr Tomasik. "Potential risk resulting from the influence of static magnetic field upon living organisms. Numerically simulated effects of the static magnetic field upon fatty acids and their glycerides." BioRisk 19 (March 6, 2023): 1–24. https://doi.org/10.3897/biorisk.19.96250.

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Background: We attempt to recognise the effects of static magnetic field (SMF) of varying flux density on flora and fauna. For this purpose, the influence of static magnetic field is studied for molecules of octadecanoic (stearic), cis-octadec-9-enoic (oleic), cis,cis-octadec-9,12-dienoic (linoleic), all cis-octadec-6,9.12-trienoic (linolenic), trans-octadec-9-enoic – (elaidic), cis-octadec-11-enoic (vaccenic) and all trans-octadec-6,9,12-trienoic (trans-linolenic) acids as well as 1- and 2-caproyl monoglycerides, 1,2- and 1,3-caproyl diglycerides and 1,2,3-caproyl triglyceride. In such a manner we attempt to develop an understanding of the interactions of living cells with SMF on a molecular level. Methods: Computations of the effect of real SMF 0.0, 0.1, 1, 10 and 100 AMFU (Arbitrary Magnetic Field Unit; here 1AMFU > 1000 T) flux density were performed in silico (computer vacuum), involving advanced computational methods. Results: SMF polarises molecules depending on applied flux density It neither ionises nor breaks valence bonds at 0.1 and 1 AMFU. In some molecules under consideration flux density of 10 and 100AMFU some C-H and C-C bonds were broken. Some irregularities were observed in the changes of positive and negative charge densities and bond lengths against increasing flux density. They provide evidence that molecules slightly change their initially fixed positions with respect to the force lines of the magnetic field. The length of some bonds and bond angles change with an increase in the applied flux density providing, in some cases, polar interactions between atoms through space. Conclusions: SMF destabilizes lipid acids and caproyl glycerides irregularly against increasing flux density. That irregularity results from the ability of those molecules to twist out of the initially established SMF plain and squeeze molecules around some bonds. In some molecules SMF flux density of 10 AMFU and above breaks some valence bonds and only in case of elaidic acid the trans-cis conversion is observed. Depending on the structure and applied flux density SMF either stimulates or inhibits metabolic processes of the lipids under study.

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12

Wang, Youliang, and Raymond A. Poirier. "Ab initio study on the thermal decarboxylation of but-3-enoic acid and its derivatives." Canadian Journal of Chemistry 72, no. 5 (1994): 1338–46. http://dx.doi.org/10.1139/v94-166.

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The mechanism for thermal decarboxylation of but-3-enoic acid and its derivatives HXC=CYCH2COOH (X, Y=H, F, CH3, C2H5, and Cl) leading to carbon dioxide and olefins has been studied from the theoretical point of view by ab initio MO calculations. The transition states obtained by our ab initio calculations are completely consistent with the experimental data, and support the "synchronous" mechanism for thermal decarboxylation of but-3-enoic acid and its derivatives via a "twisted chair" six-membered cyclic transition state. The effects of β- and γ-substituents on the activation energy (Ea) can be explained in terms of electronic charge distribution. β-Substitution decreases the activation energy, while γ-substitution increases it. Changes in the activation energy are related to changes in the charges at Cγ(C1) and Cβ(C2) as the substituents are varied. The activation energy decreases with an increase of negative charge at Cγ, while it increases with an increase of negative charge at Cβ. The best estimate of 156.8 kJ/mol for the activation energy with MP2/6-31G*//HF/3-21G(*) is in reasonable agreement with the available experimental values of 164 ± 7 kJ/mol and 160 kJ/mol for decarboxylation of but-3-enoic acid. The calculated primary kH/kD, 2.86, and [Formula: see text] 1.03, for the decarboxylation of but-3-enoic acid, are also in excellent agreement with the available experimental values of 2.7 and 1.035, respectively, supporting the transition state structure obtained.

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13

Nokami, Junzo, Masahiro Osafune, Kazuhiro Shiraishi, Shin-ichi Sumida, and Nobuyuki Imai. "Convenient synthesis of cytotoxic (11E)-13-hydroxy-10-oxooctadec-11-enoic acid from undec-10-enoic acid." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (1997): 2947–48. http://dx.doi.org/10.1039/a706245a.

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14

P., Muralidhar Reddy, Ashok M., Narasaiah V., and Ravinder V. "Synthesis, structure, reactivity and electrochemical studies of oxovanadium(IV) chelates with some carboxyamide derivatives." Journal of Indian Chemical Society Vol. 83, Oct 2006 (2006): 973–79. https://doi.org/10.5281/zenodo.5830354.

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Department of Chemistry, University Arts&. Science College, Kakatiya University, Warangal-506 001, Andhra Pradesh, India E-mail: ravichemku@yahoo.co.in <em>Manuscript received 17 November 2005, accepted 30 June 2006</em> Oxovanadium(IV) chelates of (2\(Z\))-4-(2-acetylhydrazino)-4-oxobut-2-enoic acid (AOBER), 4-(2-acetylhydrazino)- 4-oxobutanoic acid (AOBAR), 2-[(2-acetylhydrazino)carbonyl]benzoic acid (ARCBR), (2\(Z\))-4-[(2-cyanophenyl)amino]-4- oxobut-2-enoic acid (COBER), 4-[(2-cyanophenyl)amino]-4-oxobutanoic acid (COBAR), 2-[{(2-cyanophenyl)amino) carbonyl}benzoic acid (CACBR), (2\(Z\))-4-(1H-benzimidazol-2-ylamino)-4-oxobut-2-enoic acid (BOBER), 4-(1Hbenzimldazol- 2-ylamino)-4-oxobutanoic acid (BOBAR) and 2-[(1H-benzimidazol-2-ylamino)carbonyl]benzoic acid (BYCBR) have been prepared and characterized by elemental analysis, magnetic moments, IR, electronic, NMR, ESR spectra and thermal studies. The magnetic moments and electronic spectral studies suggest square pyramid geometry to all the oxovanadium(IV) complexes and distorted octahedral geometry to the vanadium(IV) complexes with O<sub>4</sub> and Cl<sub>2</sub>O<sub>4</sub> as donor sets from the ligands. The electrochemical studies by cyclic volammograms produced Irreversible single oxidation peak for V<sup>IV</sup>_V<sup>V</sup> vs SCE ranging from 0.43-0.64 V rationalized by the basicity of ligands.

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15

Dong, Su-Lan, and Xiao-Chun Cheng. "(Z)-3-(Benzylcarbamoyl)prop-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 67, no. 3 (2011): o689. http://dx.doi.org/10.1107/s160053681100609x.

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16

Yakovleva, M. P., G. R. Mingaleeva, V. A. Vydrina, A. A. Kravchenko, and G. Yu Ishmuratov. "Macrolactonization of 12R-Hydroxyoctadec-9Z-Enoic Acid." Chemistry of Natural Compounds 54, no. 6 (2018): 1149–51. http://dx.doi.org/10.1007/s10600-018-2577-7.

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17

Ananto, Agus Dwi. "Studi In Silico Bioaktivitas Antikanker Senyawa Aktif Dalam Minyak Biji Buah Wali [Brucea javanica (L.) Merr]." Sasambo Journal of Pharmacy 1, no. 2 (2020): 26–29. http://dx.doi.org/10.29303/sjp.v1i2.13.

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Insilico study of anticancer bioactivity in oil of “buah wali” [Brucea javanica (L.) Merr] has been successfully carried out. “Buah Wali” (Brucea javanica (L.) Merr) is known to treat various diseases such as diabetes, diarrhea, and malaria. In addition, “buah wali” seeds are supported to have antidiabetic, antioxidant, and anticancer activities. The stages of the study began by taking a sample of “buah wali”seeds, then extracted to get oil of “buah wali”. While GC-MS analysis resulted Octadec-9-enoic acid (56.25%), palmitic acid (13.82%), stearic acid (10.57%), and acids -9-octadecanoate (5.91%) were found as the major components of the seed oil. Based on these compounds, docking molecular was carried out to find anticancer bioactivity. The results obtained are compounds that have lower binding energy than the native ligands [Octadec-9-enoic acid (-72.4518), hexadecanoic acid (-70.2136), octadecanoic (-72.2362).

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18

Bukhari, Ishfaq A., Abdul Jabbar Shah, Kathryn M. Gauthier, et al. "11,12,20-Trihydroxy-eicosa-8(Z)-enoic acid: a selective inhibitor of 11,12-EET-induced relaxations of bovine coronary and rat mesenteric arteries." American Journal of Physiology-Heart and Circulatory Physiology 302, no. 8 (2012): H1574—H1583. http://dx.doi.org/10.1152/ajpheart.01122.2011.

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Arachidonic acid is metabolized to four regioisomeric epoxyeicosatrienoic acids (EETs) by cytochrome P-450. 5,6-, 8,9-, 11,12-, and 14,15-EET are equipotent in relaxing bovine coronary arteries (BCAs). Vasorelaxant effects of EETs are nonselectively antagonized by 14,15-epoxyeicosa-5( Z)-enoic acid. The 11,12-EET analogs, 20-hydroxy-11,12-epoxyeicosa-8( Z)-enoic acid (20-H-11,12-EE8ZE) and 11,12,20-trihydroxyeicosa-8( Z)-enoic acid (11,12,20-THE8ZE) were synthesized and tested for antagonist activity against EET-induced relaxations in BCAs. In U-46619-preconstricted arterial rings, 5,6-, 8,9-, 11,12-, and 14,15-EET caused concentration-dependent relaxations with maximal relaxations ranging from 80 to 96%. Preincubation of arteries with 20-H-11,12-EE8ZE (10−5 M) inhibited relaxations to 14,15- and 11,12-EET, but not 5,6- and 8,9-EET; however, greatest inhibitory effect was against 11,12-EET (maximal relaxation = 80.6 ± 4.6 vs. 26.7 ± 7.4% without and with 20-H-11,12-EE8ZE, respectively). Preincubation with the soluble epoxide hydrolase inhibitor (tAUCB, 10−6 M) significantly enhanced the antagonist effect of 20-H-11,12-EE8ZE against 14,15-EET-induced relaxations (maximal relaxation = 86.6 ± 4.4 vs. 27.8 ± 3.3%, without and with 20-H-11,12-EE8ZE and tAUCB) without any change in its effect against 11,12-EET-induced relaxations. In contrast to the parent compound, the metabolite, 11,12,20-THE8ZE (10−5 M), significantly inhibited relaxations to 11,12-EET and was without effect on other EET regioisomers. Mass spectrometric analysis revealed conversion of 20-H-11,12-EE8ZE to 11,12,20-THE8ZE by incubation with BCA. The conversion was blocked by tAUCB. 14,15-Dihydroxy-eicosa-5 Z-enoic acid (a 14,15-EET antagonist), but not 11,12,20-THE8ZE (an 11,12-EET antagonist), inhibited BCA relaxations to arachidonic acid and flow-induced dilation in rat mesenteric arteries. These results indicate that 11,12,20-THE8ZE is a selective antagonist of 11,12-EET relaxations and a useful pharmacological tool to elucidate the function of 11,12-EET in the cardiovascular system.

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19

Yusifova, Yuliya, and Olga Gorjacheva. "Synthesis and analysis of (2z)-4-(4-methylanilino)-4-oxobut-2-enoic acid." From Chemistry Towards Technology Step-By-Step 5, no. 2 (2024): 147–51. http://dx.doi.org/10.52957/2782-1900-2024-5-2-147-151.

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The paper identified the structure of synthesised maleic acid monoamide by physical methods of analysis. The authors have determined the solubility of maleic acid monoamide in organic solvents with different properties and dielectric constant values. The paper describes the solvent ratio allowing the analysis with the best metrological properties. The reaction between p-toluidine and maleic anhydride to form (2z)-4-(methylanilino)-4-oxobut-2-enoic acid proceeds with high yield; mass fraction of the main substance is 94.23±0.69 %.

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20

NOKAMI, J., M. OSAFUNE, K. SHIRAISHI, S. SUMIDA, and N. IMAI. "ChemInform Abstract: Convenient Synthesis of Cytotoxic (11E)-13-Hydroxy-10-oxooctadec-11-enoic Acid from Undec-10-enoic Acid." ChemInform 29, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199806256.

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21

Peppel, Tim, Marcel Sonneck, Anke Spannenberg, and Sebastian Wohlrab. "Crystal structure of (E)-hex-2-enoic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (2015): o323. http://dx.doi.org/10.1107/s2056989015007380.

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The crystal structure of the title compound, C6H10O2, an α,β-unsaturated carboxylic acid, displays carboxylic acid inversion dimers linked by pairs of O—H...O hydrogen bonds. The packing is characterized by layers of acid dimers. All the non-H atoms of the (E)-hex-2-enoic acid molecule lie almost in the same plane (r.m.s. deviation for the non-H atoms = 0.018 Å).

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22

Berkeš, Dušan, Anna Koren̆ová, Peter Šafár̆, Helena Horváthová, and Nadežda Prónayová. "Indolyl substituted 4-oxobut-2-enoic acids. Synthesis and aza-Michael additions." Open Chemistry 5, no. 3 (2007): 688–705. http://dx.doi.org/10.2478/s11532-007-0019-7.

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AbstractThe synthesis of three new substituted 4-hetereoaryl-4-oxobut-2-enoic acids with indole ring substitutedin positions 3-, 5- and 7- is described. The addition of these Michael acceptors to 4-(1-phenylsulphonylpyrrol-3-yl)-4-oxobut-2-enoic acid in conjugate addition was explored using both racemic and chiral amines. In tandem with the crystallization-induced asymmetric transformation (CIAT) protocol the effective methodology for the synthesis of enantiomerically highly enriched substituted 2-amino-4-heteroaryl-4-oxobutanoic acids as multifunctional homotryptophan analogues was developed.

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23

Siddiqi, Shahzad A., and Laxminarain Misra. "Fatty Acids and Sterols from Cymbopogon martinii var. Motia Roots." Zeitschrift für Naturforschung C 55, no. 9-10 (2000): 843–45. http://dx.doi.org/10.1515/znc-2000-9-1029.

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Abstract The hexane and methanol extracts of the roots of Cymbopogon martinii var. motia have been investigated to afford mainly fatty acids and common sterols. A new hydroxy unsaturated fatty acid, namely, 16-hydroxypentacos- 14(z)-enoic acid, has also been isolated.

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24

He, Huan, Wei Dong Du, Qiang Zhou, et al. "Three New Phenolic Compounds from Sabia parviflora and Their Hepatoprotective Activity." Natural Product Communications 17, no. 8 (2022): 1934578X2211184. http://dx.doi.org/10.1177/1934578x221118478.

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Three compounds were obtained from Sabia parviflora Wall., and their structures were identified through nuclear magnetic resonance (NMR) spectroscopy, particularly 2-dimensional (2D)-NMR. The molecular masses were determined using quadrupole-time-of-flight-mass spectrometry. Electronic circular dichroism spectra were used to determine the absolute configuration of compound 1. The 3 new compounds were identified as 2,2,7,7-tetramethyl-8S,10-dihydroxy-2,7,8,9-tetrahydro-2H-naphtha[2,3-b]pyran-6-one-10- O- β-D-glucopyranoside, (2Z)-4-(3-carboxy-4-hydroxyphenyl)-2-methylbut-2-enoic acid, and (2Z)-5-(3-carboxy-4-hydroxyphenyl)-5-oxo-2-methylpent-2-enoic acid. The liver protective activities of these compounds were tested by HepG2 and LO2 cell lines, which were induced using free fatty acids.

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Peppel, Tim, Marcel Sonneck, Anke Spannenberg, and Sebastian Wohlrab. "Crystal structure of (E)-pent-2-enoic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 5 (2015): o316. http://dx.doi.org/10.1107/s2056989015007203.

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The molecule of the title compound, C5H8O2, a low-melting α,β-unsaturated carboxylic acid, is essentially planar [maximum displacement = 0.0239 (13) Å]. In the crystal, molecules are linked into centrosymmetric dimersviapairs of O—H...O hydrogen bonds.

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26

Sonneck, Marcel, Tim Peppel, Anke Spannenberg, and Sebastian Wohlrab. "Crystal structure of (E)-undec-2-enoic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 6 (2015): o426—o427. http://dx.doi.org/10.1107/s2056989015009469.

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In the molecule of the title low-melting α,β-unsaturated carboxylic acid, C11H20O2, the least-squares mean line through the octyl chain forms an angle of 60.10 (13)° with the normal to plane of the acrylic acid fragment (r.m.s. deviation = 0.008 Å). In the crystal, centrosymmetrically related molecules are linked by pairs of O—H...O hydrogen bonds into dimers, forming layers parallel to the (041) plane.

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27

Parvez, Masood, Khadija Shahid, Saira Shahzadi, and Saqib Ali. "3-[(4-Bromoanilino)carbonyl]prop-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 60, no. 11 (2004): o2079—o2081. http://dx.doi.org/10.1107/s1600536804026029.

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Parvez, Masood, Saira Shahzadi, Khadija Shahid, and Saqib Ali. "3-[(2,4,6-Trichloroanilino)carbonyl]prop-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 60, no. 11 (2004): o2082—o2084. http://dx.doi.org/10.1107/s1600536804026030.

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29

Ortin, Yannick, and Paul Evans. "trans-Tetradec-2-enoic Acid in Impatiens glandulifera." Synthetic Communications 43, no. 10 (2013): 1404–12. http://dx.doi.org/10.1080/00397911.2011.635395.

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30

Li, Jing. "(E)-3-(3-Phenylpropoxy)but-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 62, no. 5 (2006): o1994—o1995. http://dx.doi.org/10.1107/s1600536806013778.

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In the title compound, C13H16O3, molecules related by a centre of symmetry are linked by O—H...O hydrogen bonds between the carboxyl groups to form a dimer. The propoxy chain is disordered, with an occupancy ratio of 0.69 (1):0.31 (1) between two components with roughly enantiomorphic configurations.

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31

KANG, S. K., J. H. JEON, and Y. W. PARK. "ChemInform Abstract: Enantioselective Synthesis of (4S,E)-4-Methylhex-2-enoic Acid and (4R, E)-4-Methylhex-2-enoic Acid." ChemInform 25, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199412297.

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32

Yuasa, Yoko, Yoshifumi Yuasa, and Haruki Tsuruta. "The Synthesis of (S)-3-Acetylthio-2-benzylpropionic Acid from (Z)-2-Chloromethyl-3-phenylprop-2-enoic Acid by Asymmetric Hydrogenation: a Chiral Building Block of an Enkephalinase Inhibitor." Australian Journal of Chemistry 51, no. 6 (1998): 511. http://dx.doi.org/10.1071/c97141.

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(S)-2-Benzyl-3-chloropropionic acid (7) was synthesized from (Z)-2-(chloromethyl)-3-phenylprop-2-enoic acid (5) by asymmetric hydrogenation with a ruthenium 2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl complex in the presence of triethylamine. Acetylthiolation then gave 3-acetylthio-2-benzylpropionic acid (2), a subunit of the enkephalinase inhibitor thiorphan (1).

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33

Khan, Iqra Haider, and Arshad Javaid. "Identification of Pharmaceutically Important Constituents of Quinoa Root." Jordan Journal of Pharmaceutical Sciences 16, no. 1 (2023): 96–102. http://dx.doi.org/10.35516/jjps.v16i1.1071.

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The present investigation was carried out to explore the bioactive compounds from the n-hexane fraction of methanolic extract of quinoa (Chenopodium quinoa Willd.) roots. For this purpose, C. quinoa roots were collected, shade dried, and crushed into a fine powder. The powdered material was extracted in methanol, filtered, and the filtrate was partitioned with n-hexane, followed by GC-MS analysis of the n-hexane fraction. The quantitative determination of this fraction revealed the presence of 15 phytochemical constituents of diverse nature. Among these, octadec-9-enoic acid (44.18%); n-hexadecanoic acid (18.87%); methyl (Z)-octadec-9-enoate (12.87%); methyl hexadecanoate (4.30%); 2,3-dihydroxypropyl elaidate (3.63%); phthalic acid (3.08%); methyl octadecanoate (2.27%) and 1,12-tridecadiene (2.00%) were prevailing as the most abundant to moderately occurring compounds. A thorough literature survey was carried out to collect information regarding the pharmaceutical properties of the identified compounds. It showed some of the identified compounds namely dodecanoic acid; tetradecanoic acid; 2-benzoyl-d-galactosan; n-hexadecanoic acid; methyl octadecanoate; octadec-9-enoic acid; and 2,3-dihydroxypropyl elaidate possess antifungal, antibacterial, antioxidant, antiviral, anti-inflammatory, and/or anti-cancer properties.

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34

Diamante, Daria, Sara Gabrieli, Tiziana Benincori, Gianluigi Broggini, Julie Oble, and Giovanni Poli. "Dehydrogenative Allylic Aminations of But-3-enoic Acid Derivatives." Synthesis 48, no. 19 (2016): 3400–3412. http://dx.doi.org/10.1055/s-0035-1562453.

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Two complementary Pd-catalyzed protocols enabling the γ-selective intermolecular allylic amination of but-3-enoic acid derivatives are reported. These transformations can be successfully achieved via either a direct Pd(II)-catalyzed protocol or by way of a one-pot Pd(II)/Pd(0)-catalyzed sequence, depending on the nature of the nitrogen nucleophile used.

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35

Kossuga, Miriam H., Antonio G. Ferreira, Lara D. Sette, and Roberto G. S. Berlinck. "Two Polyketides from a Co-culture of Two Marine-derived Fungal Strains." Natural Product Communications 8, no. 6 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800610.

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Co-cultivation of the fungal strains Penicillium sp. Ma(M3)V and Trichoderma sp. Gc(M2)1 in malt 2% medium led to the production of two novel, unusual polyketides, ( Z)-2-ethylhex-2-enedioic acid and ( E)-4-oxo-2-propylideneoct-7-enoic acid. Analysis of spectroscopic data enabled the structure determination of both compounds.

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36

Maggio, Antonella, Sergio Rosselli, Celeste Laura Brancazio, Vivienne Spadaro, Francesco Maria Raimondo, and Maurizio Bruno. "Metabolites from the Aerial Parts of the Sicilian Population of Artemisia alba." Natural Product Communications 8, no. 3 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800301.

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Phytochemical investigation of the CH2Cl2 extract of the aerial parts of Artemisia alba Turra afforded one new irregular sesquiterpenoid, artemiric acid, and five known metabolites: hydroxydavanone, the coumarins isofraxidin and scopoletin, (6 S*,7 S*,10 R*)–6,10-dimethyl-7,10-epoxyocta-11-enoic acid and artalbic acid. From the MeOH extract three flavonoids were identified: chrysoeriol, quercetin and isorhamnetin. The possible biogenetic pathways of artemiric and artalbic acids are discussed.

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37

Ali Shah, Farooq, Saqib Ali, Saira Shahzadi, Sajjad Ahmad, and Andreas Fischer. "(Z)-3-[(2-Fluoroanilino)carbonyl]prop-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (2011): o393. http://dx.doi.org/10.1107/s1600536811001152.

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Shah, Farooq Ali, Saqib Ali, M. Nawaz Tahir, and Sajjad Ahmed. "(2Z)-4-[(2-Hydroxyphenyl)carbamoyl]prop-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 66, no. 12 (2010): o3172. http://dx.doi.org/10.1107/s1600536810045496.

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39

Ugurchieva, T. M., A. V. Lozanova, M. V. Zlokazov, and V. V. Veselovsky. "Synthesis of (±)-4-alkanolides from pent-4-enoic acid." Russian Chemical Bulletin 57, no. 3 (2008): 657–59. http://dx.doi.org/10.1007/s11172-008-0103-y.

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40

Valkonen, Arto, Tanja Lahtinen, and Kari Rissanen. "(E)-7-(Pyren-1-yl)hept-6-enoic acid." Acta Crystallographica Section E Structure Reports Online 66, no. 7 (2010): o1837—o1838. http://dx.doi.org/10.1107/s1600536810024499.

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41

Sadiq-ur-Rehman, Saqib Ali, Saira Shahzadi, and Masood Parvez. "(E)-3-(4-Chlorophenyl)-2-phenylprop-2-enoic acid." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (2009): o1562. http://dx.doi.org/10.1107/s1600536809021904.

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42

van der Plas, H. C., and C. J. Persoons. "A new synthesis of 9-oxodec-2-enoic acid." Recueil des Travaux Chimiques des Pays-Bas 83, no. 7 (2010): 701–7. http://dx.doi.org/10.1002/recl.19640830709.

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43

Abarbri, Mohamed, Jean-Luc Parrain, Masato Kitamura, Ryoji Noyori, and Alain Duchêne. "Palladium-Catalyzed Cross-Coupling of 3-Iodobut-3-enoic Acid with Organometallic Reagents. Synthesis of 3-Substituted But-3-enoic Acids." Journal of Organic Chemistry 65, no. 22 (2000): 7475–78. http://dx.doi.org/10.1021/jo0007579.

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44

Riska, Irma Wati. "Analisis Kandungan Flavonoid pada Daun Kumis Kucing (Orthosiphon aristatus) di Desa Surabaya Kabupaten Lombok Timur." Biocaster : Jurnal Kajian Biologi 4, no. 1 (2024): 24–34. http://dx.doi.org/10.36312/biocaster.v4i1.215.

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Flavonoids are the largest group of phenolic compounds found in nature. The cat's whisker plant (Orthosiphon aristatus) is a plant that belongs to the Lamiaceae family. This plant is one of the many medicinal plants in Indonesia, and is often used by people for traditional medicine. This research aims to determine the flavonoid content found in cat's whisker leaves in Surabaya Village, East Sakra District, East Lombok Regency. This type of research is exploratory descriptive. The sample used was 392.6 grams of cat's whisker leaves. Data collection techniques are observation and documentation. The data analysis technique uses phytochemical screening and Gas Chromatography-Mass Spectroscopy (GC-MS) analysis. The research results showed that cat's whisker leaves contain flavonoids. The results of analysis using Gas Chromatography-Mass Spectroscopy (GC-MS) showed that 11 compounds were identified in the methanol extract of cat's whisker leaves (Orthosiphon aristatus). These compounds include: Methoxy, Phenyl-, Oxime, Cyclohexene, 1-methyl-4-(1-methylethenyl)-, (R)- (CAS) D-1,8, 1H-Pyrrole, 2,5-dihydro- , 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, N-Acetylpyrrolidone, 1,6-Anhydro-Beta-D- Glucopyranose, Mome Inositol (12.57%), Pluchidiol (2.38%), Beta-D-Mannofuranoside,1-O- Undecenyl)-, Octadec-9--Enoic Acid, Octadecanoic Acid (CAS) Stearic Acid. The highest content of secondary metabolite compounds is Octadec-9-Enoic Acid (21.67%).

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45

Cow, Christopher, David Valentini, and Paul Harrison. "Synthesis of the fatty acid of pramanicin." Canadian Journal of Chemistry 75, no. 6 (1997): 884–89. http://dx.doi.org/10.1139/v97-106.

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The natural product tetradec-2-enoic acid-4,5-epoxide (2), which is also a component of the antibiotic pramanicin (1), was prepared in racemic form by a glycoluril-template directed approach. Two sequential additions of acetate units to decanoic acid are effected by intramolecular condensations on the template, mimicking the proposed biosynthetic pathway to 1. Cleavage of the grown trans,trans-tetradeca-2,4-dienoyl chain from the template and epoxidation yields 2. The reaction sequence illustrates the applicability of this biomimetic approach to total synthesis of natural products. Keywords: pramanicin, biomimetic, glycoluril, template.

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46

Abdel-Lateff, Ahmed, Ehab S. Elkhayat, Mostafa A. Fouad, and Tatsufumi Okino. "Aureobasidin, New Antifouling Metabolite from Marine-Derived Fungus Aureobasidium sp." Natural Product Communications 4, no. 3 (2009): 1934578X0900400. http://dx.doi.org/10.1177/1934578x0900400315.

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Two antifouling compounds, aureobasidin (1), a new ester with an unusual 4,6-dihydroxydecanoic acid residue, and (3 R,5 S)-3,5-dihydroxydecanoic acid (2), were isolated from the marine-derived fungus Aureobasidium sp., in addition to (5 R,3 Z)-5-hydroxydec-3-enoic acid (3) and ( R)-3-hydroxydecanoic acid (4). The structures were unambiguously established by IR, 1D and 2D NMR spectroscopic and mass spectral data. Compounds 1-3 were found to be active against Bacillus subtilis, Escherichia coli and Staphyllococcus aureus. Compound 3 showed fungistatic activity against Candida albicans.

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47

Nikonov, Ivan P., Yulia O. Sharavyeva, Ramiz R. Makhmudov, Daria A. Shipilovskikh, and Irina A. Gorbunova. "SYNTHESIS, INTRAMOLECULAR CYCLIZATION AND ANTINOCICEPTIVE ACTIVITY OF 4-(HET)ARYL-2-{[3-(ETHOXYCARBONYL)-4-(4-R-PHENYL)THIOPHEN-2-YL]AMINO}- 4-OXOBUT-2-ENOIC ACIDS." ChemChemTech 67, no. 11 (2024): 22–32. https://doi.org/10.6060/ivkkt.20246711.7055.

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In this work, new substituted 4-(het)aryl-4-oxo-2-{[4-(4-R-phenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}but-2-enoic acids were studied. It was found that the intramolecular cyclisation of these acids under the action of a dehydrating agent leads to the formation of the corresponding substituted 3-(thiophen-2-yl)imino-3H-furan-2-ones, which are of great interest for further study. A content of several reaction centers in its structure allows to obtain products of heterocyclic and acyclic structure, which, at the same time, retain such important pharmacophore groups as the 2-aminothiophene fragment and 2,4-dioxobutanoic acid fragment. The studied 4-(het)aryl-4-oxo-2-{[4-(4-R-phenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}but-2-enoic acids were obtained by a one-step method, providing high yields and involving the interaction of substituted 4-(het)aryl-2-hydroxy-4-oxobut-2-enoic acids with substituted ethyl 2-amino-4-(4-R-phenyl)thiophen-3-carboxylates. The structure of the isolated final compounds was confirmed by 1H and 13C NMR spectroscopy and elemental analysis. Substituted 4-(het)aryl-4-oxo-2-thienylaminobut-2-enoic acids were then screened in vivo to detect and evaluate their biological activity and acute toxicity. The antinociceptive activity was studied in white mice of both sexes by hot plate thermal irritation intraperitonally. Acute toxicity was studied according to Pershin's method, based on observation of mice condition during 10 days after intraperitoneal injection of tested compounds. According to the results obtained, the tested compounds have a pronounced antinociceptive activity, and the acute toxicity assessment indicates that they belong to the V class of practically non-toxic drugs. High values of antinociceptive activity in combination with low toxicity makes the considered 4-(het)aryl-4-oxo-2-{[4-(4-R-phenyl)-3-(ethoxycarbonyl)thiophen-2-yl]amino}but-2-enoic acids a highly promising class for further study in order to search and develop new biologically active compounds with analgesic action and low toxicity. For citation: Nikonov I.P., Sharavyeva Yu.O., Makhmudov R.R., Shipilovskikh D.A., Gorbunova I.A. Synthesis, intramolecular cyclization and antinociceptive activity of 4-(het)aryl-2-{[3-(ethoxycarbonyl)-4-(4-R-phenyl)thiophen-2-yl]amino}-4-oxobut-2-enoic acids. ChemChemTech [Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol.]. 2024. V. 67. N 11. P. 22-32. DOI: 10.6060/ivkkt.20246711.7055.

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48

Zhestkij, N. A., E. V. Gunina, S. P. Fisenko, et al. "Synthesis of highly stable luminescent molecular crystals based on (<i>E</i>)-2-((3-(ethoxycarbonyl)-5-methyl-4-phenylthiophen-2-yl)amino)-4-oxo-4-(<i>p</i>-tolyl)but-2-enoic acid." Chimica Techno Acta 8, no. 4 (2021): 20218411. http://dx.doi.org/10.15826/chimtech.2021.8.4.11.

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The synthesis of (E)-2-((3-(ethoxycarbonyl)-5-methyl-4-phenylthiophen-2-yl)amino)-4-oxo-4-(p-tolyl)but-2-enoic acid was performed. This organic compound was used as a building block for the organic molecular crystals with highly stable photoluminescence at ambient conditions, which has been established during 10 years of exploitation.

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49

EL-Hashash, Maher A., A. Essawy, and Ahmed Sobhy Fawzy. "Synthesis and Antimicrobial Activity of Some Novel Heterocyclic Candidates via Michael Addition Involving 4-(4-Acetamidophenyl)-4-oxobut-2-enoic Acid." Advances in Chemistry 2014 (September 10, 2014): 1–10. http://dx.doi.org/10.1155/2014/619749.

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This paper discusses the utility of 4-(4-acetamidophenyl)-4-oxobut-2-enoic acid as a key starting material for the preparation of a novel series of pyridazinones, thiazoles derivatives, and other heterocycles via interaction with nitrogen, sulfur, and carbon nucleophiles under Michael addition conditions and studies the antimicrobial activities of some of these compounds.

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50

Gein, V. L., O. V. Nazarets, A. V. Romanova, et al. "Synthesis and biological activity of 4-aryl-2-hydroxy-4-oxo-<i>N</i>-(2-sulfamoylphenyl)but-2-enamides." Журнал общей химии 93, no. 5 (2023): 664–69. http://dx.doi.org/10.31857/s0044460x23050025.

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The reaction of methyl esters of 4-aryl-2-hydroxy-4-oxobut-2-enoic (aroylpyruvic) acids with 2-aminobenzenesulfonamide in glacial acetic acid in the presence of anhydrous sodium acetate, 4-aryl-2-hydroxy-4-oxo N -(2-sulfamoylphenyl)but-2-enamides were obtained. The analgesic and antimicrobial activity of the obtained compounds was studied.

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