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Journal articles on the topic 'Hydroxybenzoic'

Author: Grafiati

Published: 5 June 2025

Last updated: 24 June 2025

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1

Saruta, H., Y. Ashihara, M. Sugiyama, et al. "Colorimetric determination of carboxypeptidase A activity in serum." Clinical Chemistry 32, no. 5 (1986): 748–51. http://dx.doi.org/10.1093/clinchem/32.5.748.

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Abstract This simple, reproducible colorimetric method for determining the activity of carboxypeptidase A (EC 3.4.17.1) is based on measuring the absorbance at 505 nm of a quinoneimine dye produced from the action of this enzyme on the new substrate p-hydroxybenzoyl-glycyl-L-phenylalanine. The enzyme acts on the substrate to produce p-hydroxybenzoyl-glycine and L-phenylalanine. The former is then hydrolyzed by hippuricase (EC 3.5.1.14) to produce p-hydroxybenzoic acid and glycine. Finally, oxidative coupling of p-hydroxybenzoic acid with 4-aminoantipyrine by sodium periodate forms a quinoneimine dye. The Km for the reaction with this substrate is 3.6 mmol/L; the optimum pH is 7.8. Our within-run and between-run CVs are 4.3% and 6.6%, respectively. The activity of carboxypeptidase A in serum correlates well with that of lipase (r = 0.96) and immunoreactive elastase-1 (r = 0.76).

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2

Hopper, D. J. "Oxygenase properties of the (4-hydroxybenzoyl)methanol-cleavage enzyme from an Alcaligenes sp." Biochemical Journal 239, no. 2 (1986): 469–72. http://dx.doi.org/10.1042/bj2390469.

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Studies using H2(18)O and 18O2 demonstrated that, in the cleavage of (4-hydroxybenzoyl)methanol to 4-hydroxybenzoic and formic acids by an enzyme from an Alicaligenes sp., oxygen is incorporated into both products from dioxygen and not from water. The enzyme is, therefore, an oxygenase.

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3

Andreani, Agustina Sus, Eko Sri Kunarti, and Sri Juari Santosa. "Synthesis of Gold Nanoparticles Capped-Benzoic Acid Derivative Compounds (o-, m-, and p-Hydroxybenzoic Acid)." Indonesian Journal of Chemistry 19, no. 2 (2019): 376. http://dx.doi.org/10.22146/ijc.34440.

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The effect of a hydroxyl functional group of the benzoic acid derivative compound, i.e. o-hydroxybenzoic acid, m-hydroxybenzoic acid, and p-hydroxybenzoic acid on the synthesis of AuNPs has been studied. It was revealed that the pH, heating time, the concentration of capping agent and the concentration of Au3+ affected the formation of AuNPs. We discovered that o-hydroxybenzoic acid possessed the highest stability, yet it needed the highest concentration of Au3+ and faster reaction time than p-hydroxybenzoic acid and slower than m-hydroxybenzoic acid. The stability was verified by means of UV-Vis spectrophotometer, XRD, TEM, Particle Size Analyzer (PSA), and Zeta Potential with an aging time of more than 5 months. We concluded that o-hydroxybenzoic acid acquired the most effective redox reaction instead of m-hydroxybenzoic acid and p-hydroxybenzoic acid, resulted in the smaller sized and unaggregated AuNPs. We also confirmed that the hydroxyl group of o-hydroxybenzoic acid, m-hydroxybenzoic acid and p-hydroxybenzoic acid is the functional group responsible for the reduction of Au3+ to Au0.

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4

&NA;. "Hydroxybenzoic acids." Reactions Weekly &NA;, no. 1207 (2008): 21. http://dx.doi.org/10.2165/00128415-200812070-00063.

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5

Gusrizal, Gusrizal, Sri Juari Santosa, Eko Sri Kunarti, and Bambang Rusdiarso. "Two Highly Stable Silver Nanoparticles: Surface Plasmon Resonance Spectra Study of Silver Nanoparticles Capped with m-Hydroxybenzoic Acid and p-Hydroxybenzoic Acid." Molekul 13, no. 1 (2018): 30. http://dx.doi.org/10.20884/1.jm.2018.13.1.424.

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Silver nanoparticles capped with m-hydroxybenzoic acid and p-hydroxybenzoic have been successfully synthesized, but the long-term stability data of these silver nanoparticles are not available. In this paper, we report the stability of these two types of silver nanoparticles for a period of 40 weeks observation based on the change of surface plasmon resonance spectra of silver nanoparticles. Silver nanoparticles were synthesized by reduction of silver nitrate with m-hydroxybenzoic acid and p-hydroxybenzoic acid without addition of capping agent. The presence of silver nanoparticles was indicated by the appearance of yellow color due to the surface plasmon resonance of silver nanoparticles. The resulted silver nanoparticles were stored at room temperature and further UV-visible spectrophotometer was used to follow the change in surface plasmon resonance spectra. The surface plasmon resonance spectra of silver nanoparticles were overlapped for the first 18 weeks, followed by little change in the position of absorption maxima (lmax), peak intensity, and width of the absorption peak until the week of 40. Silver nanoparticles capped with m-hydroxybenzoic acid and silver nanoparticles capped with p-hydroxybenzoic acid were highly stable which should make them suitable for further applications. The results show the potential of m-hydroxybenzoic acid and p-hydroxybenzoic acid to become a new reducing agent in the synthesis of highly stable silver nanoparticles. The m-hydroxybenzoic acid and p-hydroxybenzoic acid appeared to act as both reducing and capping agent.

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6

Eberlein-König, B., T. Bergner, S. Diemer, and B. Przybilla. "Evaluation of phototoxic properties of some food additives: sulfites exhibit prominent phototoxicity." Acta Dermato-Venereologica 73, no. 5 (1993): 362–64. http://dx.doi.org/10.2340/0001555573362364.

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Additives are used widely to enhance the quality of food products. To identify possible phototoxic properties, 13 food additives (benzoic acid, sodium benzoate, 4/hydroxybenzoic acid, 4/hydroxybenzoic acid methyl ester, 4/hydroxybenzoic ethyl ester, 4/hydroxybenzoic acid propyl ester, p/hydroxybenzoic acid n/butyl ester, benzyl alcohol, sorbic acid, potassium sorbate, propionic acid, sodium disulfite and sodium sulfite) were evaluated in vitro by means of a photohemolysis test using suspensions of human erythrocytes. Irradiation was performed with various light sources differing with regard to their spectral irradiance. Sodium sulfite and sodium disulfite induced photohemolysis up to almost 100%, the effect depending on the concentration of the compounds and UV dose administered. Radiation rich in UVB was most effective a sunlight/simulating lamp induced photohemolysis to a lesser degree. All other substances tested did not cause significant photohemolysis. As sulfites are frequently encountered, they may contribute to UVB sensitivity. The clinical significance of these findings has to be established by further work.

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7

Gusrizal, Gusrizal, Andi Hairil Alimuddin, Ajuk Sapar, Rizki Noviani Ridwan, and Sri Juari Santosa. "Colorimetric Detection of Hg(II) Ion Using Silver Nanoparticles Capped with 3-Hydroxybenzoic Acid." Molekul 14, no. 1 (2019): 18. http://dx.doi.org/10.20884/1.jm.2019.14.1.460.

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In this paper, we report for the first time thesimple method for detection of Hg(II) ion in anaqueousmedium using silver nanoparticles capped with 3-hydroxybenzoic acid. Silver nanoparticles capped with 3-hydroxybenzoic acid were preparedby reduction of the silver ion with 3-hydroxybenzoic acid and without surface functionalization. The formation of silver nanoparticles was characterized by a UV-Visible spectrophotometer. The yellowcolloid of prepared silver nanoparticles capped with 3-hydroxybenzoic acid showed a surface plasmon resonance peak at 420 nm. The ability of silver nanoparticles capped with 3-hydroxybenzoic acid in detection was tested by doing a reaction with several metal ions individually(Na(I), K(I), Cu(II), Zn(II), Ca(II), Mg(II), Hg(II), Mn(II), Ni(II), Pb(II), and Co(II)). It was foundthat silver nanoparticles capped with 3-hydroxybenzoic acid highly selective toHg(II) and then the prepared silver nanoparticles were developedfor detection of Hg(II) ion. Addition of 1 mL Hg(II) ion into 4mL the as-preparedsilver nanoparticles reducedthe peak of surface plasmon resonance spectra, andthe reduction of peak intensity was proportional to the concentration of Hg(II) ion. A goodlinear relationship (R2= 0.998) between absorbance at 420 nm and concentrationof Hg(II) over the range 1.0x10-3to 5.5x10-3M was obtained. Silver nanoparticles capped with 3-hydroxybenzoic acid were highly sensitive to Hg (II) ion with the detection limit down to 4.7x10-5M. Application the method to the real water sample showed the excellentresult with recovery ranged from 98 to 101%. The proposed method was found to be useful forthe colorimetric detection of Hg(II) ion in an aqueousmedium.

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8

Vulpius, D., G. Geipel, and G. Bernhard. "Excited-state proton transfer of 3-hydroxybenzoic acid and 4-hydroxybenzoic acid." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 75, no. 2 (2010): 558–62. http://dx.doi.org/10.1016/j.saa.2009.11.016.

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9

Smolarz, Helena D. "Chromatographical analysis of phenolic acids in some species of Polygonum L. genus. Part 1 Qualitative analysis by two-dimensional thin layer chromatography (TLC)." Acta Societatis Botanicorum Poloniae 68, no. 4 (2014): 287–90. http://dx.doi.org/10.5586/asbp.1999.040.

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The Two-Dimensional Thin Layer Chromatography method has been used for the separation and identification of phenolic acids from six taxons of <em>Pohygonum</em> L. genus. The following acids were found: caffeic, p-coumaric, ferulic, p-hydroxybenzoic, m-hydroxybenzoic, vanillic, syringic, p-hydroxyphenylacetic, o-hydroxyphenylacetic, synapic, melillotic, salicylic, gentisic, elagic, gallic, chlorogenic, protocatechuic and homoprotocatechuic. Gallic, ferulic, vanillic, p-coumaric and p-hydroxybenzoic acids were isolated from herb <em>Polygonum convolvulus</em> L. using column chromatography.

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10

Lebedev, Anton S., and Vladimir Yu Orlov. "IDENTIFICATION OF TRANSFORMATION FUNCTIONALIZED ARENES DIRECTIONS IN NATURAL ENVIRONMENT CONDITIONS." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 7 (2020): 15–19. http://dx.doi.org/10.6060/ivkkt.20206307.6193.

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The article discusses the evaluation of the aromatic compounds pathways transformations – widespread xenobiotics of aqueous systems. This issue has both theoretical (chemical lability in complex reaction systems) and applied (target designation for the development analytical methods) meaning. Benzoic, 4-hydroxybenzoic, 2-hydroxybenzoic, 2-chlorobenzoic acids, 4-hyd-roxybenzoic acid methyl ester, and salicylic ester of acetic acid were chosen as objects of investigation. They have been used in food, pharmaceutical, cosmetic industries as preservatives, in chemical industry and laboratory practice as starting materials for the synthesis of new organic compounds, in analytical chemistry as reagents, chromophores, and standards in calorimetric analysis. We used quantum chemical modeling mechanisms of abiotic and biodegradation of functionalized arenes as a research method. It has been shown that for the transformation of benzoic acid, including oxidative breaking of cycle, the most probable is the path through 2,3-di-hydroxybenzoic acid to 1,3-butadiene-1,1,4-tricarboxylic acid (the product of the intradiol oxidative breaking of the cycle). There is transformation path through 2,3-dihydroxybenzoic acid to 1,3-butadiene-1,1,4-tricarboxylic acid (product intradiol oxidative rupture of the cycle) realized for 2-hydroxybenzoic acid (compound itself and the products of the conversion of salicylic ester of acetic acid, 2-chlorobenzoic acid). Pathway is observed through 3,4-dihydroxybenzoic acid to 1,3-butadiene-1,2,4-tricarboxylic acid (the product of the intradiol oxidative break cycle) for 4-hydroxybenzoic acid (compound itself and the product of the conversion of 4-hydroxybenzoic acid methyl ester). As it follows from the above, the intraradiol path of the oxidative cycle breaking seems to be the most preferable. Accordingly, a preferential accumulation of the following substances should be expected as results of the samples transformation: 2- and 4-hydroxybenzoic acids, 2,3- and 3,4-dihydroxybenzoic acids, products of the radical oxidative breaking of the cycle and the results of their further transformation.

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11

Rathinasabapathy, Thirumurugan, Jade Lomax, Kavin Srikanth, Debora Esposito, Colin D. Kay, and Slavko Komarnytsky. "Effect of Wild Blueberry Metabolites on Biomarkers of Gastrointestinal and Immune Health In Vitro." Immuno 2, no. 2 (2022): 293–306. http://dx.doi.org/10.3390/immuno2020019.

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Wild blueberries (Vaccinium angustifolium Aiton.) are a rich source of dietary fiber and (poly)phenols with gastrointestinal and immune health-promoting properties, however, their mechanisms of action on the intestinal epithelial cells and transient tissue macrophages remain to be elucidated. In this study, we evaluated the individual effects of anthocyanins, short-chain fatty acids (metabolites derived from fiber), and a series of hydroxycinnamic and hydroxybenzoic acid metabolites common to anthocyanins and other polyphenols on epithelial gut homeostasis in human colon epithelial CCD-18 cells and murine RAW 264.7 macrophages. Gastrointestinal cell migration was enhanced in response to anthocyanin glucosides with the maximum effect observed for malvidin-3-glucoside, and a structural subset of hydroxybenzoic acids, especially 2-hydroxybenzoic acid. Enhanced staining for ZO-1 protein in the junctional complexes was observed in CCD-18 cells treated with malvidin and butyrate, as well as several phenolic metabolites, including hydroxybenzoic and hydroxycinnamic acids. Nitric oxide production and pro-inflammatory gene expression profiles in the LPS-stimulated macrophages were mostly affected by treatments with 3-caffeoylquinic (chlorogenic) and 3,4-dihydroxycinnamic (caffeic) acids, as well as 2-hydroxybenzoic acid. This study lays the foundation for future investigations evaluating the effects of dietary interventions on managing gastrointestinal and inflammatory pathophysiological outcomes.

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12

Heath, E. A., P. Singh, and Y. Ebisuzaki. "Structure of p-hydroxybenzoic acid and p-hydroxybenzoic acid-acetone complex (2/1)." Acta Crystallographica Section C Crystal Structure Communications 48, no. 11 (1992): 1960–65. http://dx.doi.org/10.1107/s0108270192002361.

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13

Welc, Renata, Rafał Luchowski, Konrad Kłosok, Wiesław I. Gruszecki, and Agnieszka Nawrocka. "How Do Phenolic Acids Change the Secondary and Tertiary Structure of Gliadin? Studies with an Application of Spectroscopic Techniques." International Journal of Molecular Sciences 23, no. 11 (2022): 6053. http://dx.doi.org/10.3390/ijms23116053.

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The effect of the chemical structure of selected phenolic acids on the molecular organization of gliadins was investigated with the application of Fourier Transform Infrared (FTIR) technique, steady-state, and time-resolved fluorescence spectroscopy. Hydroxybenzoic (4-hydroxybenzoic, protocatechuic, vanillic, and syringic) and hydroxycinnamic (coumaric, caffeic, ferulic, sinapic) acids have been used as gliadins modifiers. The results indicated that hydroxybenzoic acids due to their smaller size incorporate into spaces between two polypeptide chains and form a hydrogen bond with them leading to aggregation. Additionally, syringic acids could incorporate into hydrophobic pockets of protein. Whereas hydroxycinnamic acids, due to their higher stiffness and larger size, separated polypeptide chains leading to gliadin disaggregation. These acids did not incorporate into hydrophobic pockets.

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14

Pechinskii, S. V., A. G. Kuregyan, and E. T. Oganesyan. "Regioselective synthesis of quercetin and myricetin derivatives." Журнал общей химии 93, no. 2 (2023): 179–87. http://dx.doi.org/10.31857/s0044460x23020038.

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A regioselective method for the synthesis of esters of quercetin and myricetin at the hydroxy group in the 3 position was developed. As acids participating in the esterification reaction, 2-hydroxybenzoic (salicylic), 4-hydroxybenzoic, 2,6-dihydroxybenzoic, 3,4-dihydroxybenzoic (procatechuic), 3,4,5-trihydroxybenzoic (gallic) acids were used. A new series of quercetin and myricetin esters were obtained.

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15

Liu, Chong-Bo, Dan-Dan Chen, and Hui-Liang Wen. "3,5-Dibromo-2-hydroxybenzoic acid." Acta Crystallographica Section E Structure Reports Online 64, no. 1 (2007): o3. http://dx.doi.org/10.1107/s1600536807062320.

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16

Yang, Yi Lin, Yuri Dyakov, Y. T. Lee, Chi-Kung Ni, Yi-Lun Sun, and Wei-Ping Hu. "Photodissociation dynamics of hydroxybenzoic acids." Journal of Chemical Physics 134, no. 3 (2011): 034314. http://dx.doi.org/10.1063/1.3526059.

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17

Ravi Kiran, Bhaskarachar, Bandrehalli Siddagangaiah Palakshamurthy, Giriyapura R. Vijayakumar, and Hebbur Shivamurthy Bharath. "3,4-Difluoro-2-hydroxybenzoic acid." Acta Crystallographica Section E Structure Reports Online 70, no. 5 (2014): o519. http://dx.doi.org/10.1107/s1600536814007211.

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In the title compound, C7H4F2O3, an intramolecular O—H...O hydrogen bond is observed. In the crystal, inversion dimers linked by pairs of O—H...O hydrogen bonds generateR22(8) ring motifs. These dimers are linked by C—H...O and C—H...F hydrogen bonds, forming sheets lying parallel to (30-1). The sheets are linked by aromatic π–π stacking interactions [inter-centroid distance = 3.7817 (9) Å], forming a three-dimensional structure.

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18

Raza, Abdul Rauf, Bushra Nisar, M. Nawaz Tahir, and Ahmad Raza. "5-Chloro-2-hydroxybenzoic acid." Acta Crystallographica Section E Structure Reports Online 66, no. 11 (2010): o2921. http://dx.doi.org/10.1107/s1600536810042042.

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19

Economy, J. "Aromatic Polyesters ofp-Hydroxybenzoic Acid." Molecular Crystals and Liquid Crystals Incorporating Nonlinear Optics 169, no. 1 (1989): 1–22. http://dx.doi.org/10.1080/00268948908062731.

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20

Sakushima, Akiyo, Maksut Coşkun, and Takashi Maoka. "Hydroxybenzoic acids from Boreava orientalis." Phytochemistry 40, no. 1 (1995): 257–61. http://dx.doi.org/10.1016/0031-9422(95)00059-g.

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21

Brel, A. K., N. V. Atapina, Yu N. Budaeva, et al. "SYNTHESIS, ANTIAGGREGATION AND ANTITROMBOTIC ACTIVITIES OF NEW DERIVATIVES OF HYDROXYBENZOIC ACIDS WITH TAURIC FRAGMENT." Pharmacy & Pharmacology 9, no. 3 (2021): 222–34. http://dx.doi.org/10.19163/2307-9266-2021-9-3-222-234.

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A high prevalence of thrombotic disorders, insufficient effectiveness or safety of antithrombotic therapy is an urgent problem of modern healthcare. The main means of preventing thrombosis is acetylsalicylic acid. Despite its long history, aspirin attracts researchers in the fields of medicinal chemistry, biology, and medicine. The development of new antiplatelet agents, including chemical modification of the acetylsalicylic acid molecule, remains relevant. Modification of the acetylsalicylic acid molecule using amino acids and obtaining their salt forms makes it possible to maintain antiplatelet or antithrombotic properties, as well as to impart additional pharmacodynamic effects. In modern science, a lot of attention is paid to the sulfur-containing amino acid taurine. An analysis of modern scientific literature revealed the protective effect of taurine in diabetes mellitus and cardiovascular diseases, liver dysfunction, gastrointestinal tract, and kidney diseases.The aim of the article is to study synthesis of new compounds, determination of their physical characteristics and assessment of their antiplatelet and antithrombotic activities in vitro and in vivo.Materials and methods. To confirm the structure of the synthesized new derivatives of hydroxybenzoic acids with a taurine fragment by the acelation method, thin layer chromatography and NMR spectra were used. In vitro studies were carried out on the model of ADP-induced platelet aggregation according to the Born G. methods modified by V.A. Gabbasov. In vivo, the studies were carried out on the model of arterial thrombosis induced by the application of iron chloride in the following groups of animals: intact, with experimental diabetes mellitus and three-year-olds; the rate of bleeding from the tail vein was also evaluated.Results. New compounds – derivatives of ortho-, meta- and para-hydroxybenzoic acids with a taurine residue – were synthesized. A procedure for the preparation of N-hydroxybenzoyl taurine compounds and their salt forms have been described; their spectral characteristics and melting points have been determined. The synthesized compounds are superior to acetylsalicylic acid in solubility and are not inferior to it in antiplatelet and antithrombotic activities. The results of the in vitro antiplatelet activity assessment in a wide concentration range from 10-4M to 10-8M, are presented. It has been revealed that the dipotassium salt of N-(2-hydroxybenzoyl)taurine exhibits a less antiplatelet activity than the dipotassium salt of N-(3-hydroxybenzoyl)taurine. The most pronounced antiplatelet activity is exhibited by the compound N-(4-hydroxybenzoyl)taurine. In in vivo experiments on the model of arterial thrombosis in 3-year-olds or animals with experimental diabetes mellitus, carotid artery thrombosis occurred faster than in young or intact animals. A single preliminary oral administration of the test compounds prolonged the time of the thrombus formation, which makes it possible to conclude that they have an antithrombotic effect. In this study, the dipotassium salt of N-(3-hydroxybenzoyl)taurine exhibits a more pronounced activity than that of acetylsalicylic acid.Conclusion. Against the background of the modeled pathologies, the studied drugs showed the expected antithrombotic activity, in terms of the severity not inferior to that found in acetylsalicylic acid.

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22

Smolarz, Helena D., and Tadeusz Krzaczek. "Phytochemical studies of the herb, Tragopogon orientalis L. (Asteraceae). 2. Components of a methanol extract." Acta Societatis Botanicorum Poloniae 57, no. 1 (2014): 93–105. http://dx.doi.org/10.5586/asbp.1988.009.

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Vitexin, orientin, isoorientin, luteolin and apigenin were isolated from the herb, <em>Tragopogon orientnlis</em> L. The occurrence of quercetin and the phenolic acids: chlorogenic, homoprotoca-techuic, protocatechuic, caffeic, gentysic, p-hydroxybenzoic, m-hydroxybenzoic o-hydroxyphenylacetic, p-hydroxyphenylacetic, p-cumaric, syringic, vanillic, ferulic and salicylic, and of the sugars: glucose, fructose and sucrose was demonstrated chromatographically.

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23

Susanthy, Dian, Fadliah, Endang Tri Wahyuni, and Sri Juari Santosa. "Synthesis of Silver Nanoparticles Using o-Hydroxybenzoic, p-Hydroxybenzoic, and o,p-Dihydroxybenzoic Acids as Reducing Agents." Materials Science Forum 901 (July 2017): 26–31. http://dx.doi.org/10.4028/www.scientific.net/msf.901.26.

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Synthesis of silver nanoparticles (AgNPs) by reduction of AgNO3 with o-hydroxybenzoic, p-hydroxybenzoic and o,p-dihydroxybenzoic acids as reducing agents was investigated. This research was conducted to determine the effect of the position and number of hydroxyl groups towards the size, shape and stability of the resulted AgNPs. Surface Plasmon Resonance (SPR) of AgNPs was characterized by UV/Vis spectrophotometer, the shape and size of AgNPs was determined by Transmission Electron Microscope (TEM). The results showed that the reducing agent that has substituents in the para position (p-hydroxybenzoic acid) has the higher reduction ability than the others. AgNPs were yielded by all types of reducing agents in alkaline system. Reducing agents which have greater number of substituents (o,p-dihydroxybenzoic acid) could produce AgNPs with smaller concentration of AgNO3 than the others. AgNPs that was produced by reducing agent having substituents on the para position (p-hydroxybenzoic acid) was more stable and smaller particle size, i.e. 34 ± 1.78 nm than reducing agent that has substituent on the ortho para positions (with particle size 45 + 3.67 nm) and ortho positions (with particle size 70 ± 4.96 nm).

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24

Chung, I. M., J. K. Ahn, and S. J. Yun. "Identification of allelopathic compounds from rice (Oryza sativa L.) straw and their biological activity." Canadian Journal of Plant Science 81, no. 4 (2001): 815–19. http://dx.doi.org/10.4141/p00-191.

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Experiments were conducted to identify allelochemicals from rice (Oryza sativa L.) straw extracts of four rice cultivars (Gin shun, Kasawala mundara, Philippine 2 and Juma 10), and to test their biological activity on barnyard grass (Echinochloa crus-galli P. Beauv. var. oryzicola Ohwi). High performance liquid chromatography (HPLC) analysis showed that the concentration and composition of allelopathic compounds depended on the cultivar. Among the compounds identified were p-hydroxybenzoic acid at 6.87 mg g–1 in Gin shun, p-coumaric acid at 0.34 mg g–1 in Kasawala mundara, ferulic acid at 0.05 mg g–1 in Philippine 2, and p-hydroxybenzoic acid at 6.34 mg g–1 in Juma 10. Preliminary identification by HPLC analysis resulted in peaks with retention times near those of standards, including p-hydroxybenzoic acid m/z = 138). This was confirmed with electron impact/mass spectra. In a bioassay with nine known allelochemicals and their mixtures, p-hydroxybenzoic acid (10–3 M) showed the greatest inhibitory effect on barnyard grass seed germination, seedling length, and dry weight. This suggests that this compound may be a key factor in rice allelopathy on barnyard grass. Key words: Allelopathic compound, rice, barnyard grass, bioassay

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25

Moncol, Ján, Klaudia Jomová, and Mária Porubská. "Two centrosymmetric dinuclear phenanthroline–copper(II) complexes with 3,5-dichloro-2-hydroxybenzoic acid and 5-chloro-2-hydroxybenzoic acid." Acta Crystallographica Section C Crystal Structure Communications 68, no. 4 (2012): m85—m89. http://dx.doi.org/10.1107/s0108270112004532.

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The title compounds, bis(μ-3,5-dichloro-2-oxidobenzoato)-κ3O1,O2:O2;κ3O2:O1,O2-bis[(3,5-dichloro-2-hydroxybenzoic acid-κO1)(1,10-phenanthroline-κ2N,N′)copper(II)], [Cu2(C7H2Cl2O3)2(C7H4Cl2O3)2(C12H8N2)2], (I), and bis(μ-5-chloro-2-oxidobenzoato)-κ3O1,O2:O1;κ3O1:O1,O2-bis[(5-chloro-2-hydroxybenzoic acid-κO1)(1,10-phenanthroline-κ2N,N′)copper(II)] ethanol monosolvate, [Cu2(C7H3ClO3)2(C7H5ClO3)2(C12H8N2)2]·C2H6O, (II), contain centrosymmetric dinuclear complex molecules in which Cu2+cations are surrounded by a chelating 1,10-phenanthroline ligand, a chelating 3,5-dichloro-2-oxidobenzoate or 5-chloro-2-oxidobenzoate anionic ligand and a monodentate 3,5-dichloro-2-hydroxybenzoic acid or 5-chloro-2-hydroxybenzoic acid ligand. The chelating benzoate ligand also bridges to the other Cu2+ion in the molecule, but the O atom involved in the bridge is different in the two complexes, being the phenolate O atom in (I) and a carboxylate O atom in (II). The bridge completes a 4+1+1 axially elongated tetragonal–bipyramidal arrangement about each Cu2+cation. The complex molecules of both compounds are linked into one-dimensional supramolecular chains through O—H...O hydrogen bonds.

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26

Silva, Hélio Cândido da, Vanessa Herrig, Maria de Lourdes L. Ferrarese, and Osvaldo Ferrarese-Filho. "Consumption of ferulic and p-hydroxybenzoic acids by soybean root tips." Brazilian Archives of Biology and Technology 43, no. 3 (2000): 281–84. http://dx.doi.org/10.1590/s1516-89132000000300006.

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Depletion method was used to describe how soybean root consumed ferulic and p-hydroxybenzoic acids in nutrient culture. The results showed that excised cultured soybean roots consumed these allelochemicals very rapidly. At concentrations between 0.1 and 1.0 mM, roots consumed 50% or more of ferulic acid after 6-h depletion. Although consumption started only after 3 h, similar behavior was verified with p-hydroxybenzoic acid.

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Krzaczek, Tadeusz, and Monika Gawrońska-Grzywacz. "Free and bound phenolic acids in inflorescences and rhizomes with roots of Hieracium pilosella L. (Asteraceae)." Acta Societatis Botanicorum Poloniae 75, no. 3 (2011): 215–18. http://dx.doi.org/10.5586/asbp.2006.025.

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The analysis of the fractions of free and bound, liberated by hydrolysis, phenolic acids in the inflorescences and rhizomes with roots of <em>Hieracium pilosella</em> L. was conducted by 2D-TLC and RP-HPLC methods. In the inflorescences fourteen phenolic acids were found: chlorogenic, gallic, protocatechuic, homoprotocatechuic, caffeic, gentisic, p-hydroxyphenylacetic, p-hydroxybenzoic, m-hydroxybenzoic, p-coumaric, syringic, vanillic, ferulic and salicylic. In the rhizomes with roots nine phenolic acids were identified: chlorogenic, gallic, homoprotocatechuic, caffeic, gentisic, p- hydroxyphenylacetic, p-hydroxybenzoic, syringic and vanillic. By means of the RP-HPLC method the contents of major acids were estimated which ranged from 0.01 mg% up to 139.50 mg%. Caffeic acid is the remarkably dominating constituent of both plant materials. Phenolic compounds may contribute to invasiveness and medicinal properties of this species.

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Yoshioka, Takeo, Tomohisa Inokuchi, Shozo Fujioka, and Yasuo Kimura. "Phenolic Compounds and Flavonoids as Plant Growth Regulators from Fruit and Leaf of Vitex rotundifolia." Zeitschrift für Naturforschung C 59, no. 7-8 (2004): 509–14. http://dx.doi.org/10.1515/znc-2004-7-810.

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AbstractFive phenolic compounds, 4-hydroxybenzoic acid methyl ester (1), vanillic acid methyl ester (2), 4-hydroxy benzaldehyde (3), 4-hydroxybenzoic acid (4) and ferulic acid (5), and four flavonoids, 5,5′-dihydroxy-4′,6,7-trimethoxyflavanone (6), luteolin (7), vitexicarpin (8) and artemetin (9), were isolated from fruits and leaves of Vitex rotundifolia L. The biological activities of these nine compounds have been examined using a bioassay with lettuce seedlings.

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29

Chirag Dhamsania and Sanghadiya Divyang G. "To control the para-Hydroxybenzoic Acid during the synthesis of Sodium Methyl Paraben Preservative." IJPAR JOURNAL 13, no. 4 (2024): 705–8. https://doi.org/10.61096/ijpar.v13.iss4.2024.705-708.

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Sodium Methyl Paraben (SMP) is the sodium salt of Methyl Paraben. Para-Hydroxybenzoic acid is most common Degradation impurity of Sodium Methyl Paraben. There are several mechanisms involves the formation of Para-Hydroxybenzoic Acid (PHBA) as an impurity during Sodium Methyl Paraben (SMP) synthesis. Mainly Parent paraben readily undergo base-catalyzed hydrolysis of the ester bond, forming PHBA. Solvent may affect the formation of PHBA, mainly the role of Methanol.

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30

Margesin, Rosa, Thomas Marek Ludwikowski, Andrea Kutzner, and Andreas Otto Wagner. "Low-Temperature Biodegradation of Lignin-Derived Aromatic Model Monomers by the Cold-Adapted Yeast Rhodosporidiobolus colostri Isolated from Alpine Forest Soil." Microorganisms 10, no. 3 (2022): 515. http://dx.doi.org/10.3390/microorganisms10030515.

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The contribution of cold-adapted yeasts to the emerging field of lignin biovalorization has not yet been studied. The red-pigmented basidiomycetous yeast strain Rhodosporidiobolus colostri DBVPG 10655 was examined for its potential to degrade five selected lignin-derived aromatic monomers (syringic acid, p-coumaric acid, 4-hydroxybenzoic acid, ferulic acid, and vanillic acid). The strain utilized p-coumaric acid, 4-hydroxybenzoic acid, and ferulic acid not only as the sole carbon source; full biodegradation occurred also in mixtures of multiple monomers. Vanillic acid was not utilized as the sole carbon source, but was degraded in the presence of p-coumaric acid, 4-hydroxybenzoic acid, and ferulic acid. Syringic acid was utilized neither as the sole carbon source nor in mixtures of compounds. Biodegradation of lignin-derived aromatic monomers was detected over a broad temperature range (1–25 °C), which is of ecological significance and of biotechnological relevance.

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31

Peng, Xue, Norihiko Misawa, and Shigeaki Harayama. "Isolation and Characterization of Thermophilic Bacilli Degrading Cinnamic, 4-Coumaric, and Ferulic Acids." Applied and Environmental Microbiology 69, no. 3 (2003): 1417–27. http://dx.doi.org/10.1128/aem.69.3.1417-1427.2003.

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ABSTRACT Thirty-four thermophilic Bacillus sp. strains were isolated from decayed wood bark and a hot spring water sample based on their ability to degrade vanillic acid under thermophilic conditions. It was found that these bacteria were able to degrade a wide range of aromatic acids such as cinnamic, 4-coumaric, 3-phenylpropionic, 3-(p-hydroxyphenyl)propionic, ferulic, benzoic, and 4-hydroxybenzoic acids. The metabolic pathways for the degradation of these aromatic acids at 60°C were examined by using one of the isolates, strain B1. Benzoic and 4-hydroxybenzoic acids were detected as breakdown products from cinnamic and 4-coumaric acids, respectively. The β-oxidative mechanism was proposed to be responsible for these conversions. The degradation of benzoic and 4-hydroxybenzoic acids was determined to proceed through catechol and gentisic acid, respectively, for their ring fission. It is likely that a non-β-oxidative mechanism is the case in the ferulic acid catabolism, which involved 4-hydroxy-3-methoxyphenyl-β-hydroxypropionic acid, vanillin, and vanillic acid as the intermediates. Other strains examined, which are V0, D1, E1, G2, ZI3, and H4, were found to have the same pathways as those of strain B1, except that strains V0, D1, and H4 had the ability to transform 3-hydroxybenzoic acid to gentisic acid, which strain B1 could not do.

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Kotsupii, Olga Viktorovna, and Tatyana Aleksandrovna Shemetova. "FEATURES OF ACCUMULATION OF PHENOLIC COMPOUNDS IN ENDEMIC SPECIES ASTRAGALUS IONAE PALIBIN AND A. PALIBINII POLOZHIJ GROWING ON THE TERRITORY OF THE REPUBLIC OF KHAKASIA." chemistry of plant raw material, no. 2 (May 23, 2024): First. http://dx.doi.org/10.14258/jcprm.20240212441.

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The features of the accumulation of flavonoid glycosides and hydroxybenzoic and hydroxycinnamic acids have been studied in the leaves of endemic Astragalus ionae Palibin and A. palibinii Polozhij of different ecological and geographical growing conditions of the Republic of Khakasia by HPLC method. Luteolin-7-glucoside, rutin, kaempferol-3-O-β-rutinoside, and 3 quercetin glycosides were identified from 8 glycosides of flavonoids from the leaves of A. ionae plants. Six flavonoid glycosides were found in the leaves of A. palibinii, luteolin-7-glucoside, rutin, kaempferol-3-O-β-rutinoside, and isorhamnetin-3-O-β-rutinoside were identified. No differences were found in the composition of hydroxybenzoic and hydroxycinnamic acids in plants of the studied taxa. Gallic, p-hydroxybenzoic, neochlorogenic, chlorogenic, caffeic, p-coumaric, and ferulic acids were identified in the leaves of A. ionae and A. palibinii. The differences between these species in terms of the content of phenolic compounds are most pronounced in the fact that A. ionae plants accumulate more luteolin-7-glucoside, the sum of flavonoid glycosides, and hydroxybenzoic acids. The content of phenolic compounds in plants of different coenopopulations is influenced by ecological and coenotic factors. In arid xerophytic and petrophytic communities more characteristic of these species, more caffeic acid and rutin accumulate, as well as the amount of hydroxycinnamic acids.

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33

Gao, Ruo-Xuan, Yuan-Yuan Gao, Ning Zhu, and Li-Min Han. "CO2 Improved Synthesis of Benzimidazole with the Catalysis of a New Calcium 4-Amino-3-hydroxybenzoate." Acta Chimica Slovenica 68, no. 1 (2021): 205–11. http://dx.doi.org/10.17344/acsi.2020.6359.

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In this paper, we explored the synthesis of benzimidazole by the reaction of DMF and o-phenylenediamine. In the process of catalyst screening, we found that 4-amino-3-hydroxybenzoic acid, benzoic acid, and benzene-1,3,5-tricarboxylic acid could catalyze the reaction. Moreover, the calcium 4-amino-3-hydroxybenzoate and CO2 could more effectively catalyze the reaction, the synergistic effect of CO2 and 4-amino-3-hydroxybenzoic acid calcium salt can increase the yield of benzimidazole from 28% to 94%.

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34

Flippen-Anderson, Judith L., Jeffrey R. Deschamps, Arnold Brossi, and Nigel H. Greig. "2-Hydroxybenzoic acid salt of physostigmine." Acta Crystallographica Section E Structure Reports Online 58, no. 8 (2002): o853—o855. http://dx.doi.org/10.1107/s1600536802012278.

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35

Stadthagen, Gustavo, Jana Korduláková, Ruth Griffin, et al. "p-Hydroxybenzoic Acid Synthesis inMycobacterium tuberculosis." Journal of Biological Chemistry 280, no. 49 (2005): 40699–706. http://dx.doi.org/10.1074/jbc.m508332200.

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36

Collado, Sergio, Irene Rosas, Cristina González, and Mario Diaz. "Biodegradation ofp-hydroxybenzoic acid byPseudomonas putida." Desalination and Water Treatment 57, no. 32 (2015): 15230–40. http://dx.doi.org/10.1080/19443994.2015.1072584.

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37

Brel, A. K., S. V. Lisina, S. S. Popov, and Yu N. Budaeva. "Amidation of hydroxybenzoic acids with imidazole." Russian Journal of General Chemistry 86, no. 3 (2016): 742–44. http://dx.doi.org/10.1134/s1070363216030403.

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38

Ko, Ya-Wen, Pen-Chi Chiang, and E. E. Chang. "Ozonation of p-Hydroxybenzoic Acid Solution." Ozone: Science & Engineering 20, no. 5 (1998): 343–60. http://dx.doi.org/10.1080/01919519809480347.

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39

Kricheldorf, Hans R., Arnd Conradi, Ralf Pakull, and Gert Schwarz. "Thermotropic copolyesters of 4-hydroxybenzoic acid." Makromolekulare Chemie. Macromolecular Symposia 26, no. 1 (1989): 25–46. http://dx.doi.org/10.1002/masy.19890260105.

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40

Schwarz, Gert, and Hans R. Kricheldorf. "New polymer synthesis. 39. Thermotropic copolyesters of 4-hydroxybenzoic acid and 3-chloro-4-hydroxybenzoic acid." Macromolecules 23, no. 6 (1990): 1568–74. http://dx.doi.org/10.1021/ma00208a002.

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41

Goto, Ayako, Hiroshi Miyamoto, Mark Salomon, et al. "IUPAC-NIST Solubility Data Series. 90. Hydroxybenzoic Acid Derivatives in Binary and Ternary Systems. Part II. Hydroxybenzoic Acids, Hydroxybenzoates, and Hydroxybenzoic Acid Salts in Nonaqueous Systems." Journal of Physical and Chemical Reference Data 40, no. 2 (2011): 023102. http://dx.doi.org/10.1063/1.3569816.

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42

Yıldırım, Zeliha, Yaselin İlk, and Metin Yıldırım. "Enterosin KP’nin Antibakteriyal Aktivitesi Üzerine Para-Hidroksi-Benzoik Asit ile Propil-Parabenin Sinerjit Etkisi." Turkish Journal of Agriculture - Food Science and Technology 2, no. 1 (2014): 1. http://dx.doi.org/10.24925/turjaf.v2i1.1-5.35.

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In this study, the effects of food preservative p-hydroxybenzoic acid and propyl-paraben on the inhibitory activity of enterocin KP produced by Enterococcus faecalis KP were determined. Staphylococcus aureus, Escherichia coli O157:H7 and Salmonella Typhimurium, resistant to enterocin KP bacteriocin, were used as target organisms. The inhibitor activity of enterosin KP (1600 AU/ml) alone or in combination with p-hydroxybenzoic acid (%0.1-0.3) and propyl-paraben (%0.008-0.16) on the growth of Staphylococcus aureus, Escherichia coli O157:H7 and Salmonella Typhimurium were determined. The inhibitory activity of enterocin KP was increased when used in combination with p-hydroxybenzoic acid and propyl-paraben at concentrations of 0.1-0.3% and 0.008-0.016%, respectively. Furthermore, Staphylococcus aureus, E. coli O157:H7 and Salmonella Typhimurium became sensitive to enterocin KP. In conclusion, the use of enterocin KP in combination with other food preservatives principles resulted in an increase in its inhibitory activity and spectrum.

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43

Aiello, Donatella, Tiziana Marino, Anna Napoli, Emilia Furia, and Pierluigi Plastina. "Evaluation of Solubility and Complexation Ability of Vanillic, Syringic and Gallic Acids Towards Aluminum Cation." Inorganics 13, no. 1 (2024): 2. https://doi.org/10.3390/inorganics13010002.

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Chelation therapy is currently successfully applied to reduce the aluminum burden and its neurodegenerative consequences. In view of a possible application to aluminum chelation therapy, here we have studied the complexation of hydroxybenzoic acids, namely, vanillic, syringic and gallic acids, towards aluminum ion at physiologically relevant conditions as regards temperature (37 °C) and ionic strength (i.e., 0.16 M NaCl). The solubility values and the protonation constants of the hydroxybenzoic acids were primarily assessed to estimate the competition of these acids towards aluminum and H+ ions. Then, potentiometric titrations were carried out, and the speciation analysis indicated a pH-dependent complexation occurring at a 1:1 hydroxybenzoic acid-to-aluminum ratio for vanillic and syringic, and 1:1, 2:1 and 3:1 ligand-to-Al(III) ratios for gallic. Gallic acid forms more stable complexes with Al(III) ion than vanillic and syringic acids and could therefore represent a good candidate for being used as sequestering agents for Al(III) ion.

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44

Tang, Daojian, Guishui Zhang, Ya Wang, Fengxia Chen, and Jiahai Ma. "The reactivity and pathway of Fenton reactions driven by hydroxybenzoic acids: the effect of hydroxylation." Environmental Science: Water Research & Technology 5, no. 9 (2019): 1507–14. http://dx.doi.org/10.1039/c9ew00250b.

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45

Sun, Wenli, and Mohamad Hesam Shahrajabian. "Therapeutic Potential of Phenolic Compounds in Medicinal Plants—Natural Health Products for Human Health." Molecules 28, no. 4 (2023): 1845. http://dx.doi.org/10.3390/molecules28041845.

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Phenolic compounds and flavonoids are potential substitutes for bioactive agents in pharmaceutical and medicinal sections to promote human health and prevent and cure different diseases. The most common flavonoids found in nature are anthocyanins, flavones, flavanones, flavonols, flavanonols, isoflavones, and other sub-classes. The impacts of plant flavonoids and other phenolics on human health promoting and diseases curing and preventing are antioxidant effects, antibacterial impacts, cardioprotective effects, anticancer impacts, immune system promoting, anti-inflammatory effects, and skin protective effects from UV radiation. This work aims to provide an overview of phenolic compounds and flavonoids as potential and important sources of pharmaceutical and medical application according to recently published studies, as well as some interesting directions for future research. The keyword searches for flavonoids, phenolics, isoflavones, tannins, coumarins, lignans, quinones, xanthones, curcuminoids, stilbenes, cucurmin, phenylethanoids, and secoiridoids medicinal plant were performed by using Web of Science, Scopus, Google scholar, and PubMed. Phenolic acids contain a carboxylic acid group in addition to the basic phenolic structure and are mainly divided into hydroxybenzoic and hydroxycinnamic acids. Hydroxybenzoic acids are based on a C6-C1 skeleton and are often found bound to small organic acids, glycosyl moieties, or cell structural components. Common hydroxybenzoic acids include gallic, syringic, protocatechuic, p-hydroxybenzoic, vanillic, gentistic, and salicylic acids. Hydroxycinnamic acids are based on a C6-C3 skeleton and are also often bound to other molecules such as quinic acid and glucose. The main hydroxycinnamic acids are caffeic, p-coumaric, ferulic, and sinapic acids.

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46

Gurbuzer, Aslihan. "Investigation of in vitro antimicrobial activities of some hydroxybenzoic and hydroxycinnamic acids commonly found in medicinal and aromatic plants." International Journal of Plant Based Pharmaceuticals 1, no. 1 (2021): 42–47. http://dx.doi.org/10.62313/ijpbp.2021.3.

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Since hospital-acquired microorganisms are developing more and more resistance to antibiotics used today, researchers are turning to new searches in the treatment of infectious diseases. Unfortunately, unconscious use of antibiotics is another important reason why microorganisms develop resistance to infectious diseases. The aim of this study was to test the antimicrobial activity of some hydroxybenzoic and hydroxycinnamic acids on various gram-positive and gram-negative bacteria and a yeast strain (C. albicans). Agar well diffusion and minimum inhibitory concentration (MIC) tests were applied to determine the antimicrobial activities of phenolic acids. Considering the activity findings of phytochemicals on all test microorganisms, they were ranked in terms of their activities with a statistical method called the relative inhibitory capacity index (RICI) (a method that was first introduced in the literature by the current study). RICI analysis showed that the most effective phenolic acids for all test microorganisms were sinapic acid and 4-hydroxybenzoic acid. The RICI coefficients of these compounds were 1.02 and 0.99, respectively. Sinapic acid exhibited a zone of inhibition of 9.00-27.00 mm and an MIC of 18.00-72.00 mg/ml on microorganisms. Inhibition zone and MIC value ranges of 4-hydroxybenzoic acid were determined as 9.00-16.00 mm and 36.00-72.00 mg/ml, respectively. RICI analyzes confirmed that 2-phenylbutyric acid and phloroglucinol carboxylic acid did not show any antimicrobial activity. It is thought that sinapic acid and 4-hydroxybenzoic acid can be used as alternative antimicrobial agents against multi drug resistant microorganisms.

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47

Gurbuzer, Aslihan. "Investigation of in vitro antimicrobial activities of some hydroxybenzoic and hydroxycinnamic acids commonly found in medicinal and aromatic plants." International Journal of Plant Based Pharmaceuticals 1, no. 1 (2021): 42–47. https://doi.org/10.5281/zenodo.6384189.

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Since hospital-acquired microorganisms are developing more and more resistance to antibiotics used today, researchers are turning to new searches in the treatment of infectious diseases. Unfortunately, unconscious use of antibiotics is another important reason why microorganisms develop resistance to infectious diseases. The aim of this study was to test the antimicrobial activity of some hydroxybenzoic and hydroxycinnamic acids on various gram-positive and gram-negative bacteria and a yeast strain (C. albicans). Agar well diffusion and minimum inhibitory concentration (MIC) tests were applied to determine the antimicrobial activities of phenolic acids. Considering the activity findings of phytochemicals on all test microorganisms, they were ranked in terms of their activities with a statistical method called the relative inhibitory capacity index (RICI) (a method that was first introduced in the literature by the current study). RICI analysis showed that the most effective phenolic acids for all test microorganisms were sinapic acid and 4-hydroxybenzoic acid. The RICI coefficients of these compounds were 1.02 and 0.99, respectively. Sinapic acid exhibited a zone of inhibition of 9.00-27.00 mm and an MIC of 18.00-72.00 mg/ml on microorganisms. Inhibition zone and MIC value ranges of 4-hydroxybenzoic acid were determined as 9.00-16.00 mm and 36.00-72.00 mg/ml, respectively. RICI analyzes confirmed that 2-phenylbutyric acid and phloroglucinol carboxylic acid did not show any antimicrobial activity. It is thought that sinapic acid and 4-hydroxybenzoic acid can be used as alternative antimicrobial agents against multi drug resistant microorganisms.

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48

Sedlák, Petr, Stanislav Luňák, and Pavel Lederer. "Comparison of photocatalytic activities of 3d transition metal ions for hydrogen peroxide photolysis and photoinitiated hydroxylation of 2-hydroxybenzoic acid." Collection of Czechoslovak Chemical Communications 52, no. 10 (1987): 2451–56. http://dx.doi.org/10.1135/cccc19872451.

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Quantum yields of hydrogen peroxide photolysis and photoinitiated hydroxylation of 2-hydroxybenzoic acid in the presence of 3d transition metal ions have been measured. Marked photocatalytic effects were only observed for Cu(II) in hydrogen peroxide photolysis, and for Fe(III) in photoinitiated hydroxylation of 2-hydroxybenzoic acid. No photocatalytic activity was detected for the other 3d transition metal ions investigated. Fe(III) and Cu(II) differ in their photocatalytic activities, suggesting that the simple concept of free OH. radical formation cannot explain the mechanisms of their action.

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49

Mardjan, Muhammad Idham Darussalam, Retno Ambarwati, Sabirin Matsjeh, Tutik Dwi Wahyuningsih, and Winarto Haryadi. "SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE." Indonesian Journal of Chemistry 12, no. 1 (2012): 70–76. http://dx.doi.org/10.22146/ijc.21374.

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Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.

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50

Leyte-Lugo, Martha, Pascal Richomme, Pascal Poupard, and Luis M. Peña-Rodriguez. "Identification and Quantification of a Phytotoxic Metabolite from Alternaria dauci." Molecules 25, no. 17 (2020): 4003. http://dx.doi.org/10.3390/molecules25174003.

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Alternaria dauci is the causal agent of Alternaria leaf blight (ALB) in carrot (Daucus carota) crops around the world. However, to date, A. dauci has received limited attention in its production of phytotoxic metabolites. In this investigation, the bioassay-guided isolation of the extract from liquid cultures of A. dauci resulted in the isolation of two metabolites identified as α-acetylorcinol (1) and p-hydroxybenzoic acid (2), based on their spectroscopic data and results from chemical correlation reactions. Testing of both metabolites in different assays showed an important phytotoxic activity for p-hydroxybenzoic acid (2) when tested in the leaf-spot assay on parsley (Petroselinum crispum), in the leaf infiltration assay on tobacco (Nicotiana alata) and marigold (Tagetes erecta), and in the immersion assay on parsley and parsnip (Pastinaca sativa) leaves. Quantification of the two metabolites in the crude extract of A. dauci kept at different times showed that p-hydroxybenzoic acid (2) is one of the first metabolites to be synthesized by the pathogen, suggesting that this salicylic acid derivative could play an important role in the pathogenicity of the fungus.

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