3 hydroxycoumarin

Manufactured by Merck Group

Sourced in United States

3-Hydroxycoumarin is a chemical compound that is commonly used as a laboratory reagent. It is a white crystalline solid that is soluble in organic solvents. 3-Hydroxycoumarin has a core function as a fluorescent dye and can be used in various analytical and research applications.

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5 protocols using 3 hydroxycoumarin

Synthesis and Characterization of Coumarin Analogues

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Buprofezin (672928, HPC Standards GmbH, Germany), Etoxazole (675816, HPC Standards GmbH, Germany), Lufenuron (673891, HPC Standards GmbH, Germany), Triflumuron (675080, HPC Standards GmbH, Germany), Difebenzurone (674699, HPC Standards GmbH, Germany), Nikkomicin Z from Streptomyces tendae (N8028, Sigma-Aldrich, St. Louis, MO, USA), 4-Methylubelliferone (M1381, Sigma-Aldrich, St. Louis, MO, USA), 3-Hydroxycoumarin (642673, Sigma-Aldrich, St. Louis, MO, USA; compound I) and 7-Methoxy-4-methylcoumarin (246131, Sigma-Aldrich, St. Louis, MO,USA; compound II).
Analogues of 4-MU were synthesized in the laboratory Taras Shevchenko National University of Kyiv, Faculty of chemistry, using the protocol described previously (Moskvina and Khilya 2008 ; Moskvina et al. 2014 ; Glibov et al. 2018 ). The detailed synthesis is described in Supplementary. All substances were dissolved in DMSO (A1584, AppliChem GmbH, Germany).

Tsitrina A.A., Krasylov I.V., Maltsev D.I., Andreichenko I.N., Moskvina V.S., Ivankov D.N., Bulgakova E.V., Nesterchuk M., Shashkovskaya V., Dashenkova N.O., Khilya V.P., Mikaelyan A, & Kotelevtsev Y. (2021). Inhibition of hyaluronan secretion by novel coumarin compounds and chitin synthesis inhibitors. Glycobiology, 31(8), 959-974.

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Antibacterial Activity of Commercial Coumarins

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All commercial coumarins (1,2-Benzopyrone 1; 3-Hydroxycoumarin 2; 4-Hydroxycoumarin 3; 6-Hydroxycoumarin 4; 7-Hydroxycoumarin 5; 6,7-Dihydroxycoumarin 6; Coumarin-3-carboxylic acid 7; 3,3′-Methylene-bis-(4-Hydroxycoumarin) 8; 6-Methoxy-7-Hydroxycoumarin 9; and 7,8-Dihydroxy-6-methoxycoumarin 10), reagents, and solvents were purchased from Sigma-Aldrich (Seelze, Germany) and used without further purification. Norfloxacin, erythromycin, and tetracycline were obtained from Sigma Chemical Co., USA, and their stock solutions were then prepared [15 ]. Compounds 11–22 were synthesized according to previously reported procedures [12 (link)]. The stock solutions of coumarin derivatives 1–22 were prepared in DMSO. The highest concentration remaining after broth dilution (4%) did not inhibit bacterial growth, and a positive control with only DMSO 4% was tested and showed no interference with bacterial growth (data not shown).

de Araújo R.S., Barbosa-Filho J.M., Scotti M.T., Scotti L., da Cruz R.M., Falcão-Silva V.D., de Siqueira-Júnior J.P, & Mendonça-Junior F.J. (2016). Modulation of Drug Resistance in Staphylococcus aureus with Coumarin Derivatives. Scientifica, 2016, 6894758.

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Quantitative Analysis of Coumarin and Its Metabolites

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Coumarin and 4-Hydroxycoumarin were obtained from Acros organics, 3-Hydroxycoumarin, 3-(2-Hydroxyphenyl) propionic acid, and 7-hydroxycoumarin (7OHC) were obtained from Sigma-Aldrich, trans-o-Coumaric acid was obtained from Tokyo chemical Industry Co., and 6-Hydroxycoumarin was obtained from Fisher scientific. All chemicals had purities of 98 % or higher. Methanol (≥99.8 %) and acetic acid (≥99.8 %) were procured from Fisher Scientific and Sigma Aldrich, respectively. All chemicals were used as received. Stock solutions of coumarin (8.2 mM) and its products (100 μM) were prepared to their desired concentration and diluted using distilled water when required. Calibration curves for each chemical were prepared using their associated stock solution and analysed using high performance liquid chromatography (HPLC). HPLC mobile phases were prepared using deionised water. The initial concentration of coumarin for this study was 100 µM (15 ppm), as followed in our previous study pertaining to dosimetry [26] .

De-Nasri S.J., Sarvothaman V.P., Nagarajan S., Manesiotis P., Robertson P.K, & Ranade V.V. (2022). Quantifying OH radical generation in hydrodynamic cavitation via coumarin dosimetry: Influence of operating parameters and cavitation devices. Ultrasonics Sonochemistry, 90, 106207.

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Synthesis and Characterization of Hydroxycoumarin Compounds

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Coumarin (99%),
7-hydroxyCoumarin (99%), 6-hydroxyCoumarin (96%), 4-hydroxyCoumarin,
3-hydroxyCoumarin (98%), and potassium phosphate solutions (1.0 M)
were purchased from Sigma-Aldrich, USA. 8-HydroxyCoumarin was obtained
from MedChemExpress. 5-HydroxyCoumarin was synthesized with slight
modification according to a method by Adams and Bockstahler (1952).^{39 (link)} The Aeroxide P25 photocatalyst was purchased
from Evonik Degussa, Germany. Methanol (≥99.9%), acetonitrile
(≥99.9%) formic acid, and acetic acid (≥99.8%) were
of HPLC grade and purchased from Sigma-Aldrich. Millipore water (18
MΩ cm) was used for the preparation of all aqueous solutions.
All chemicals used were of analytical reagent grade and used as received.

McCormick W.J., Rice C., McCrudden D., Skillen N, & Robertson P.K. (2023). Enhanced Monitoring of Photocatalytic Reactive Oxygen Species: Using Electrochemistry for Rapid Sensing of Hydroxyl Radicals Formed during the Degradation of Coumarin. The Journal of Physical Chemistry. a, 127(23), 5039-5047.

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Analysis of Roasted Coffee Compounds

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Methanol, acetonitrile, and formic acid of MS-grade were supplied from Fisher Scientific (Hampton, New Hampshire, USA). Ammonium formate of MS grade, 4-O-caffeoylquinic acid, quinic acid, shikimic acid, 3-hydroxycoumarin, 7-hydroxycoumarin, trans-caffeic, caffeic acid, trans-ferulic acid, chlorogenic acid, neochlorogenic acid 1-aminocyclohexanecarboxylic acid, methyl benzoate, betaine, nor valine, valine, proline, and choline were purchased from Sigma (St. Louis, MO, USA). Ultrapure water was generated with a Milli-Q system (Millipore, Madrid, Spain).
Green coffee beans (GCB) of the Arabica variety were roasted to light (LRC), medium (MRC), and dark (DRC) levels at 175, 185, and 195 °C during 12.36, 14.11, and 17.06 min, respectively. In order to control the roasting process, the weight loss of each sample was checked, being 13% in light coffee, 15% in medium coffee, and 17% in dark coffee. All these coffee samples were kindly donated, roasted, and grounded by “Café Fortaleza” (Vitoria, Spain) and were identical to the samples analyzed in our previous works using RPLC-MS [25 (link)] and CE-MS [26 (link)] platforms.

Pérez-Míguez R., Castro-Puyana M., Sánchez-López E., Plaza M, & Marina M.L. (2020). Untargeted HILIC-MS-Based Metabolomics Approach to Evaluate Coffee Roasting Process: Contributing to an Integrated Metabolomics Multiplatform. Molecules, 25(4), 887.

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