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Hydroxybenzoic acid

Hydroxybenzoic acid is a family of organic compounds consisting of a benzene ring with one or more hydroxyl (-OH) groups attached.
These compounds are widely found in nature and have various biological and industrial applications.
They play important roles in plant metabolism, act as antioxidants, and have potential therapeutic uses.
Researchers can utilize PubCompare.ai's AI-driven protocol comparison tool to optimize their hydroxybenzoic acid studies, identify the best published procedures, and achieve reproducibility in their experiments.
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Most cited protocols related to «Hydroxybenzoic acid»

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Publication 2004
Acetic Acid Anthocyanins Chalcones Coumaric Acids Coumarins Curcuminoid Ellagitannins Flavanones Flavones Flavonols formic acid Gallotannins High-Performance Liquid Chromatographies Hydroxybenzoic Acids Isoflavones Leucoanthocyanidins Lignans Medicinal Herbs Methanol Proanthocyanidins Quinones Retention (Psychology) sodium phosphate Stilbenes Tannins
Extending the ClusterBlast analysis that identifies homologous gene clusters across many published genome sequences, we have added a new option to identify operons related to the biosynthesis of precursors or specific chemical moieties in a gene cluster’s end product. This new analysis module, SubclusterBlast, performs blastp searches of the amino acid translations of all cluster genes against a database containing 126 sub-clusters from gene clusters encoding known compounds (Figure 2). These sub-clusters code for the biosynthesis of precursors, such as 6-methylsalicylic acid, 3-amino-5-hydroxybenzoic acid, ethylmalonyl-CoA, deoxysugars and hydroxyphenylglycine, which are highly specific for certain classes of bioactive compounds. Hence, their presence in a genome allows more confident conclusions about the biosynthetic capacities of an organism. The hits are sorted in the same way as the ClusterBlast hits (17 (link)), but they are gathered with stricter thresholds: a minimal percentage identity of 45% and a minimal sequence coverage of 40% are required. The highest-scoring sub-cluster hits are then displayed on the results page using an annotated vector graphic similar to the general ClusterBlast output.

ClusterBlast and SubclusterBlast outputs for the balhimycin (23 (link)) biosynthesis gene cluster. The top six hits of each analysis module are shown. The ClusterBlast module shows the homology between the balhimycin gene cluster and the vancomycin, VEG, A40926 and teicoplanin biosynthesis gene clusters. Homologous genes are shown in identical colors, whereas white-colored genes have no BLAST hits between the gene clusters. The novel SubclusterBlast module can identify homologous sub-clusters encoding the biosynthesis of specific chemical moieties. In this case, SubclusterBlast is able to identify the dihydroxyphenylglycine (dHpg), hydroxyphenylglycine (Hpg) and hydroxytyrosine (Bht) precursor biosynthesis sub-clusters, as well as the vancosamine-like sugar biosynthesis sub-cluster.

Publication 2013
3-amino-5-hydroxybenzoic acid 6-methylsalicylic acid A 40926 Amino Acids Anabolism balhimycin Carbohydrates Cloning Vectors Deoxy Sugars dihydroxyphenylglycine ethylmalonyl-coenzyme A Gene Clusters Genes Genome Operon Protein Biosynthesis Protein S Self Confidence Teicoplanin Vancomycin vancosamine
Phenolics in crude extracts and each fraction of lingonberries were identified and quantified by HPLC-PDA (Waters e2695 Alliance system, Waters, Milford, MA, USA) according to Raudone et al. with some modifications [27 (link)]. Chromatographic separation was carried out on an ACE C18 reversed-phase column (250 mm × 4.6 mm, particle size 3 µm; ACT, UK) with a gradient elution consisting of 0.1% trifluoroacetic acid in water (eluent A) and acetonitrile (eluent B) at a flow rate of 0.5 mL/min, injection volume of 10 µL, and column temperature maintained at 35 °C. The gradient pattern was 0 min, 10% B; 0–40 min, 30% B; 40–60 min, 70% B; 60–64 min, 90% B; 64–70 min, 10% B. Prior to HPLC-PDA analysis, all samples were dissolved in 70% ethanol until complete dissolution, obtaining a concentration of 1 mg/mL, and filtered through a pore size 0.2 µm PVDF syringe filters (Macherey-Nagel GmbH & Co. KG, Düren, Germany).
The described modified method was validated following international guidelines [28 ]. The selectivity of peaks was evaluated and phenolic compounds were identified by comparing the retention times, UV spectra of the analytes with those of the reference compounds, and on the basis of previous reports on lingonberry phenolics. The PDA detector was set at a wavelength of 280 nm for proanthocyanidins and catechins, 360 nm for flavonols, 520 nm for anthocyanins, 330 for hydroxycinnamic acids, and 260 nm for hydroxybenzoic acids. All phenolics were quantified according to 5–7 points linear calibration curves of external standards, except well-known predominant compounds of lingonberry leaves—quercetin-3-O-(4”-(3-hydroxy-3-methylglutaryl)-rhamnoside (quercetin-HMG-rhamnoside), and 2-O-caffeoylarbutin, because of commercially unavailable standards. They were tentatively quantified using calibration curves of standard substances with similar chemical structures. Limits of detection (LOD) and of quantification (LOQ) were determined via the signal-to-noise ratio method. The trueness of the method was expressed as percent recoveries of phenolics at low, medium, and high concentrations of range, each analyzed in triplicate. To assess the repeatability and intermediate precision of the method, relative standard deviation percentages (% RSD) of peak areas of each quantified phenolic compound were calculated within (six times per day) and between days (three consecutive days), respectively, resulting in total repeatability of 18 replicates.
Publication 2020
acetonitrile Anthocyanins Catechin Chromatography Complex Extracts Coumaric Acids Ethanol Flavonols Genetic Selection High-Performance Liquid Chromatographies Hydroxybenzoic Acids Lingonberry polyvinylidene fluoride Proanthocyanidins Quercetin Retention (Psychology) Syringes Trifluoroacetic Acid
In this study, most of the chemicals, reagents, and standards were analytical grade and purchased from Sigma-Aldrich (Castle Hill, NSW, Australia). Gallic acid, L-ascorbic acid, vanillin, hexahydrate aluminium chloride, Folin-Ciocalteu’s phenol reagent, sodium phosphate, iron(III) chloride hexahydrate (Fe[III]Cl3.6H2O), hydrated sodium acetate, hydrochloric acid, sodium carbonate anhydrous, ammonium molybdate, quercetin, catechin, 2,2′-diphenyl-1-picrylhy-drazyl (DPPH), 2,4,6tripyridyl-s-triazine (TPTZ), and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) were purchased from the Sigma-Aldrich (Castle Hill, NSW, Australia) for the estimation of polyphenols and antioxidant potential. Sulfuric acid (H2SO4) with 98% purity was purchased from RCI Labscan (Rongmuang, Thailand). HPLC standards including gallic acid, p-hydroxybenzoic acid, caftaric acid, caffeic acid, protocatechuic acid, sinapinic acid, chlorogenic acid, syringic acid, ferulic acid, coumaric acid, catechin, quercetin, quercetin-3-galactoside, diosmin, quercetin-3-glucuronide, epicatechin gallate, quercetin-3-glucoside, kaempferol and kaempferol-3-glucoside were produced by Sigma-Aldrich (Castle Hill, NSW, Australia) for quantification proposes. HPLC and LC-MS grade reagents including methanol, ethanol, acetonitrile, formic acid, and glacial acetic acid were purchased from Thermo Fisher Scientific Inc. (Scoresby, VIC, Australia). To perform various in vitro bioactivities and antioxidant assays, 96 well-plates were bought from the Thermo Fisher Scientific (VIC, Australia). Additionally, HPLC vials (1 mL) were procured from the Agilent technologies (VIC, Australia).
Publication 2020
2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid 4-hydroxybenzoic acid Acetic Acid acetonitrile Aluminum Chloride ammonium molybdate Antioxidants Ascorbic Acid Biological Assay caffeic acid caftaric acid Catechin Chlorides Chlorogenic Acid Coumaric Acids Diosmin diphenyl epicatechin-3-gallate Ethanol ferulic acid folin formic acid Gallic Acid Glucosides High-Performance Liquid Chromatographies Hydrochloric acid hyperoside Iron isoquercetin kaempferol Methanol Phenol Polyphenols protocatechuic acid Quercetin quercetin 3-O-glucuronide sinapinic acid Sodium Acetate sodium carbonate sodium phosphate Sulfonic Acids Sulfuric Acids syringic acid Triazines vanillin
Betalains and phenolic compounds were determined simultaneously by high-performance liquid chromatography [8 (link)]. A 1200 Series Agilent HPLC System (Agilent Technologies, Santa Clara, CA, USA) with a reverse-phase C18 column (Zorbax SB-C18, 250 × 4.6 mm i.d., S-5 µm; Agilent) at 25 °C was used. Mobile phase A was 1% formic acid (v/v) in ultrapure water and mobile phase B was 1% formic acid (v/v) in methanol. Separation was achieved using an initial composition of 15% B during 15 min, increased to 25% within 10 min, subsequentially ramped to 50% B within 10 min, increased to 75% B in 15 min, and finally followed by a decrease period of 15% B in 5 min prior to isocratic re-equilibration for 10 min. The flow rate was 0.8 mL/min and the injection volume was 20 µL. The UV-visible photodiode array detector was set at four wavelengths to detect phenolic acids (280 nm), flavonoids (370 nm), betaxanthins (480 nm), and betacyanins (535 nm). UV/Vis spectra were additionally recorded between 200 and 700 nm. The HPLC-DAD was coupled to a mass spectrometry detector (LCMS SQ 6120, Agilent, Agilent Technologies, Santa Clara, California, USA) with an electrospray ionization (ESI) source operating in positive ion mode. The drying gas was nitrogen at 3 L/min at 137.9 KPa. The nebulizer temperature was 300 °C and the capillary had 3500 V potential. The coliseum gas was helium and the fragmentation amplitude were 70 V. Spectra were recorded m/z from 100 to 1000.
Further mass spectrometry analyses were performed in a maXis II LC-QTOF equipment (Bruker Daltonics, Bremen, Germany) with an ESI source and the same chromatographic conditions. The ESI-QTOF detector worked in positive ion mode and recorded spectra m/z from 50 to 3000. Operation conditions were 300 °C, capillary voltage 3500 V, charging voltage 2000 V, nebulizer 2.0 bar, and dry gas at 6 L/min. MS/MS analysis used the bbCID (Broad Band Collision Induces Dissociation) method at 30 eV.
Compounds were identified according to their retention times, UV/Vis, and mass spectral data compared to those of commercial, semi-synthesized, or purified standards. Identification and quantitation of portulacaxanthin, vulgaxanthin I and II, indicaxanthin, betanin, betanidin, piscidic acid, isorhamnetin glycosides (IG1, IG2, IG3, IG4, IG5, and IG7), kampferol glycoside (KG1), and rutin were determined using standards and their respective calibration curves. Quercetin glycosides were quantified by using the rutin calibration curve. Remaining betalains were quantified using the calibration curves of betalains of similar molecular weight. 4-hydroxybenzoic acid derivative was quantified using the calibration curve for 4-hydroxybenzoic acid. The identification of betalains and phenolic compounds in prickly pears is presented in Table 2.
Publication 2020
3-methylquercetin 4-hydroxybenzoic acid Betacyanins Betalains Betanidins betanin Betaxanthins Capillaries Chromatography Flavonoids formic acid GAS6 protein, human Glycosides Helium High-Performance Liquid Chromatographies hydroxybenzoic acid indicaxanthin kaempferol Lincomycin Mass Spectrometry Methanol Nebulizers Nitrogen Opuntia piscidic acid Quercetin Retention (Psychology) Rutin Tandem Mass Spectrometry vulgaxanthin-I Z-100

Most recents protocols related to «Hydroxybenzoic acid»

Example 18

[Figure (not displayed)]

Step 1: Methyl 2-methoxy-5-(4,7,8-trichloroquinolin-2-yl)benzoate. To a suspension of 2,4,7,8-tetrachloroquinoline (200 mg, 0.75 mmol) with (4-methoxy-3-(methoxycarbonyl)phenyl) boronic acid (205.3 mg, 0.98 mmol) and Na2CO3 (178 mg, 1.68 mmol) in dioxane (8.0 mL) and water (2.0 mL) was added Pd(PPh3)4 (79.2 mg). The resultant mixture was vacuumed and purged with N2 for three cycles, then stirred and heated at 80° C. over two hours. After cooling to room temperature, the reaction mixture was dissolved in DCM (50 mL) and washed with water and brine. The resultant organic layer was separated and dried over anhydrous Na2SO4. A silica gel flash column chromatography eluting with DCM/Hexane afforded the desired colorless product (MS: [M+1]+ 396).

Step 2: 2-Hydroxy-5-(4,7,8-trichloroquinolin-2-yl)benzoic acid (I-75). Methyl 2-methoxy-5-(4,7,8-trichloroquinolin-2-yl) benzoate (17 mg) in DCM (1.5 mL) was treated with 1M BBr3 in DCM (0.1 mL) at room temperature over 8 hours. The resulting mixture was diluted with EtOAc (25 mL), washed with water (10 mL) and dried over Na2SO4. Concentration under vacuum afforded the desired light brown solid (11 mg), 2-hydroxy-5-(4,7,8-trichloroquinolin-2-yl) benzoic acid (MS: [M+1]+ 368).

Step 3: 5-(7,8-dichloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-hydroxybenzoic acid. To a solution of 2-hydroxy-5-(4,7,8-trichloroquinolin-2-yl) benzoic acid (11 mg) in DMF (0.5 mL) was added imidazole (55 mg) and K2CO3 (50 mg). The resultant solution was stirred and heated at 120° C. over 5 hours until the starting material was completely consumed. The reaction mixture was diluted with water (3 mL) and treated with Dowex resin until the pH to 3. The resultant colorless solid was isolated by filtration and washed with water (3 mL). After drying under vacuum, the desired product was obtained (MS: [M+1]+ 400).

Patent 2024

Example 12

[Figure (not displayed)]

Step 1: Methyl 5-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-methoxybenzoate was prepared according to the procedure above to prepare compound I-2.

Step 2: 5-(7-Chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-hydroxybenzoic acid (I-16) was prepared according to the procedure above to prepare compound I-26. (MS: [M+1]+ 366).

Step 3: Ethyl 5-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-ethoxybenzoate. To a vial were added 5-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-hydroxybenzoic acid (14 mg, 0.0383 mmol), ethyl iodide (22 μl, 0.274 mmol), Cs2CO3 (62 mg, 0.191 mmol) and DMF (1.0 mL). The resulting reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (40 mL), washed by H2O (4×20 mL) and brine (15 mL). After concentration, the crude was used in next step.

Step 4: 5-(7-Chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-2-ethoxybenzoic acid. To the crude product above were added MeOH (0.6 mL), THF (0.4 mL) and a solution of NaOH in H2O (7.66 mg/0.2 mL). The resulting reaction mixture was stirred at room temperature overnight. Then the mixture was diluted by H2O (3 mL) and acidified by HOAc to pH 4. The cloudy mixture was centrifuged and the residue was washed by H2O (2×1.5 mL), dried over high vacuum to afford the title product as off-white solid (6 mg) (MS: [M+1]+ 394).

Patent 2024
To the mixture of methyl 5-(cyano(phenylamino)methyl)-2-hydroxybenzoate (I10) (200 mg, 0.71 mmol) and K2CO3 (98 mg, 0.71 mmol) in DMSO (0.9 mL) was added 30% H2O2 (0.11 ml, 1.06 mmol) at 0°C. The mixture was warmed to rt and stirred for 2 hours. The precipitate was collected by filtration, washed with cold water and dried in vacuo. The residue was dissolved in a mixture of MeOH/H2O (4:1, 5 mL) and NaOH (113 mg, 2.83 mmol) was then added. This reaction mixture was refluxed for 5 hour and concentrated. Water (30 mL) was added and the resulting mixture was extracted with EtOAc (20 mL). The aqueous phase was acidified to pH = 4 with conc. HCl, and extracted with DCM (3 x 20 mL). The combined DCM layer was washed with brine, dried over Na2SO4, filtered and the solvent was evaporated to give product (60 mg, 30% yield). 1H NMR (300 MHz, DMSO-d6) δ 11.56–10.89 (brs, 1H), 7.92 (d, J = 2.4 Hz, 1H), 7.63 (dd, J = 8.6, 2.4 Hz, 1H), 7.07–6.99 (m, 2H), 6.95 (d, J = 8.6 Hz, 1H), 6.64 (d, J = 7.6 Hz, 2H), 6.54 (t, J = 7.3 Hz, 1H), 5.06 (s, 1H). 13C NMR (101 MHz, MeOD) δ 175.07, 173.31, 162.99, 147.83, 135.77, 130.60, 130.33, 130.01, 119.00, 118.50, 114.87, 113.98, 61.25. HRMS (ESI) for C14H12NO3 [M—CO2H]+, calcd 242.0817, found 242.0829. LC-MS: m/z calculated for C15H14NO5 [M+ H+]: 288; found 288. Purity by HPLC analysis on Adamas C18: at 210 nm—93.26%; at 254 nm—92.95%.
Publication 2024

Example 11

[Figure (not displayed)]

Step 1: 3-(4,7-dichloroquinolin-2-yl)-5-methoxybenzoic acid was prepared essentially by the same methods described above to prepare I-2.

Step 2: 3-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-5-methoxybenzoic acid. To a vial were added 3-(4,7-dichloroquinolin-2-yl)-5-methoxybenzoic acid (50 mg, 0.144 mmol), imidazole (49 mg, 0.718 mmol), Cs2CO3 (70 mg, 0.216 mmol) and DMF (1.0 mL). The resulting reaction mixture was stirred at 110° C. overnight. At room temperature the reaction mixture was diluted by H2O (4 mL) and acidified by HCl (1 N) to pH about 3. A lot of white solid precipitated, centrifuged and washed by H2O (2×4 mL). The residue was dried in vacuo to afford the titled compound as white solid (30 mg). MS: [M+1]+ 380.

Step 3: 3-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-5-hydroxybenzoic acid. To a vial were added 3-(7-chloro-4-(1H-imidazol-1-yl)quinolin-2-yl)-5-methoxybenzoic acid (7.9 mg, 0.0208 mmol), NaI (20 mg, 0.133 mmol) and HBr in HOAc (33%, 1.0 mL). The resulting mixture was stirred at 50° C. overnight. The mixture was cooled to room temperature and diluted by H2O (10 mL), centrifuged, and washed with H2O (4 mL). The residue was dried under high vacuum to afford the title product as off-white solid (18 mg) (MS: [M+1]+ 366).

Patent 2024
Compound was obtained according general procedure to give product (43 mg, 18%). 1H NMR (400 MHz, MeOD-d4) δ 8.20 (d, J = 2.4 Hz, 1H), 7.75 (dd, J = 8.8, 2.4 Hz, 1H), 7.23 (dd, J = 8.1, 6.6 Hz, 2H), 7.17–7.02 (m, 5H), 7.01–6.95 (m, 3H), 3.87 (s, 2H). 13C NMR (101 MHz, MeOD) δ 172.37, 166.29, 142.49, 139.73, 136.76, 134.86, 131.66, 131.30, 130.64, 129.80, 129.43, 127.05, 123.14, 119.00, 113.94, 41.98. HRMS (ESI) for C20H18NO5S [M+H]+, calcd 384.0906, found 384.0896. Purity by HPLC analysis on Apollo C18: at 210 nm—95.96%; at 254 nm—97.02%.
Publication 2024

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Gallic acid is a naturally occurring organic compound that can be used as a laboratory reagent. It is a white to light tan crystalline solid with the chemical formula C6H2(OH)3COOH. Gallic acid is commonly used in various analytical and research applications.
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Caffeic acid is a phenolic compound commonly found in various plants. It serves as a laboratory standard for the identification and quantification of similar phenolic compounds using analytical techniques such as high-performance liquid chromatography (HPLC) and spectrophotometry.
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P-coumaric acid is a naturally occurring phenolic compound that can be utilized as a reference standard or an analytical reagent in various laboratory settings. It is a white to off-white crystalline solid that is soluble in organic solvents. P-coumaric acid is commonly used as a standard in analytical techniques, such as high-performance liquid chromatography (HPLC) and spectrophotometric measurements, to quantify and characterize similar compounds in sample matrices.
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Ferulic acid is a phenolic compound that can be found in various plant sources, including rice, wheat, oats, and vegetables. It is commonly used as a lab equipment product for research and analysis purposes. Ferulic acid has antioxidant properties and can be used in a variety of applications, such as the study of plant-based compounds and their potential health benefits.
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Vanillic acid is a chemical compound that is commonly used in laboratory settings. It is a white, crystalline solid with a characteristic vanilla-like odor. Vanillic acid is often used as a reference standard in analytical methods and as a precursor in the synthesis of other chemical compounds.
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Quercetin is a natural compound found in various plants, including fruits and vegetables. It is a type of flavonoid with antioxidant properties. Quercetin is often used as a reference standard in analytical procedures and research applications.
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4-hydroxybenzoic acid is a chemical compound used in various laboratory applications. It is a crystalline solid with the chemical formula C₇H₆O₃. The compound serves as a precursor for the synthesis of other chemicals and is utilized in various research and development processes.
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Chlorogenic acid is a compound found in various plants, including coffee beans. It is a type of polyphenol and is commonly used in laboratory settings for research purposes.
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Syringic acid is a phenolic compound that can be used as a chemical reagent in laboratory research and analysis. It serves as a standard reference material for analytical techniques such as chromatography and spectroscopy. The specific core function of syringic acid is to act as a calibration and measurement standard for the quantification of similar phenolic compounds in various samples.
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P-hydroxybenzoic acid is a chemical compound that serves as a versatile intermediate for the synthesis of various pharmaceutical and industrial products. It is a white or colorless crystalline solid that has a melting point around 214°C. P-hydroxybenzoic acid is commonly used as a starting material in the production of certain drugs, personal care products, and other chemical derivatives.

More about "Hydroxybenzoic acid"

Phenolic acids, Phenolcarboxylic acids, Gallic acid, Caffeic acid, p-Coumaric acid, Ferulic acid, Vanillic acid, Quercetin, 4-hydroxybenzoic acid, Chlorogenic acid, Syringic acid, p-Hydroxybenzoic acid