4 hydroxyphenylacetic acid

Manufactured by Merck Group

Sourced in United States, Germany, Spain

4-hydroxyphenylacetic acid is a chemical compound used in various laboratory applications. It is a colorless, crystalline solid with the molecular formula C8H8O3. The compound serves as a building block and intermediate in organic synthesis.

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Lab products found in correlation

24 protocols using 4 hydroxyphenylacetic acid

Integrated Gut Microbiome Modulation

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Formic acid, bile salts, soluble starch, (+)-arabinogalactan, tryptone, yeast extract, xylan from birchwood, L-cysteine hydrochloride monohydrate, guar gum, inulin, Tween 80, buffered peptone water, Dulbecco′s phosphate buffer saline (PBS), casein sodium salt from bovine milk, pectin from citrus fruits, mucin from porcine stomach-type III, CaCl₂, KCl, NaCl, NaHCO₃, anhydrous K₂HPO₄, KH₂PO₄, MgSO₄ monohydrate, FeSO₄ heptahydrate, resazurin redox indicator, quercetin, kaempferol, quercetin-3-O-rutinoside (aka rutin), phenylacetic acid, 4′-hydroxyphenylacetic acid, 3′-hydroxyphenylacetic acid, 3′,4′-dihydroxyphenylacetic acid, 3-phenylpropanoic acid, 3-(4′-hydroxyphenyl)propanoic acid, 3-(3′-hydroxyphenyl)propanoic acid, 3-(3′,4′-dihydroxyphenyl)propanoic acid (aka dihydrocaffeic acid), 4-hydroxybenzoic acid, 3-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid (aka protocatechuic acid), and benzene-1,3,5-triol (aka phloroglucinol) were obtained from Sigma-Aldrich (St Louis, MO, USA). Isorhamnetin was from PhytoLab GmbH (Vestenbergsgreuth, Germany). All solvents and water were UHPLC-grade and were purchased from VWR International (Milan, Italy).

Di Pede G., Bresciani L., Calani L., Petrangolini G., Riva A., Allegrini P., Del Rio D, & Mena P. (2020). The Human Microbial Metabolism of Quercetin in Different Formulations: An In Vitro Evaluation. Foods, 9(8), 1121.

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Synthesis and Purification of Sulfonated Aromatic Compounds

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All solvents used for isolation, synthesis and analytical studies were of analytical grade and purchased from Merck (Darmstadt, Germany). HPLC grade water was produced by a Sartorius arium 611 UV water purification system (Sartorius Göttingen, Germany). Reagents for the synthesis of 4-(sulfooxy)benzoic acid and 4-(sulfooxy)phenylacetic acid (4-hydroxybenzoic acid, sulphur trioxide pyridine complex (Pyr*SO₃), and 4-hydroxyphenylacetic acid) were purchased from Sigma Aldrich (Taufkirchen, Germany). Deuterated water for NMR experiments was obtained from Euriso-top (Saint-Aubin Cedex, France).

Hartmann A., Ganzera M., Karsten U., Skhirtladze A, & Stuppner H. (2018). Phytochemical and Analytical Characterization of Novel Sulfated Coumarins in the Marine Green Macroalga Dasycladus vermicularis (Scopoli) Krasser. Molecules, 23(11), 2735.

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Identification and Quantification of Organic Compounds

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All chemicals were of analytical grade. Amino acid standard AAS18 (Sigma-Aldrich Chemical Co., St. Louis, MO, USA) was used for the identification of amino acids. Lactic acid, benzoic acid, succinic acid, 4-hydroxybenzaldehyde, 3- phenylpropionic acid, malic Acid, 4-methoxyphenylacetic acid, Gamma-Aminobutyric acid, trans-Cinnamic acid, 3-hydroxybenzoic acid, 4-hydroxybenzoic acid, 4-hydroxyphenylacetic acid, adonitol, hydrocinnamic acid, 3,4-dihydroxyphenylacetic acid, citric acid, D-Fructose, d-Galactose, d-Glucose, 3,4-dihydroxyhydrocinnamic acid, 3-(4-hydroxyphenyl)propionic acid, 1H-indole-3-acetic Acid, D-mannitol, dextrose, sucrose, indole, were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA) and used for identification purposes. Stock solutions of all the analytical standards were prepared by dissolving the compounds in MilliQ water.

Jain A., Li X.H, & Chen W.N. (2019). An untargeted fecal and urine metabolomics analysis of the interplay between the gut microbiome, diet and human metabolism in Indian and Chinese adults. Scientific Reports, 9, 9191.

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Comprehensive Metabolite Extraction and Analysis

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Optima LC/MS grade methanol and water; and JT Baker potassium sorbate, sodium carbonate, Invitrogen Trizol reagent; and ACS grade chloroform, methanol, and ethanol were purchased from Fisher Scientific (Waltham, MA, USA). Citric acid, 1 N Folin–Ciocalteu reagent, 99% formic acid, (−)-epicatechin, naringenin, quercetin, cyanidin chloride, ellagic acid, gallic acid, 4-hydroxyphenylpropionic acid, 4-hydroxyphenylacetic acid, enterodiol, hippuric acid, 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) (ABTS), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), potassium persulphate were purchased from Sigma-Aldrich (St. Louis, MO, USA). M-MLV RT, M-MLV 5× reaction buffer, oligo (dT)15 primer, dNTP mix, SybrGreen master mix, and RNAse-free water were purchased from Promega.

Sotelo-González A.M., Reynoso-Camacho R., Hernández-Calvillo A.K., Castañón-Servín A.P., García-Gutiérrez D.G., Gómez-Velázquez H.D., Martínez-Maldonado M.Á., de los Ríos E.A, & Pérez-Ramírez I.F. (2023). Strawberry, Blueberry, and Strawberry-Blueberry Blend Beverages Prevent Hepatic Steatosis in Obese Rats by Modulating Key Genes Involved in Lipid Metabolism. International Journal of Environmental Research and Public Health, 20(5), 4418.

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Organosolv Lignin Tyrosinase Immobilization

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Organosolv lignin (OL) was purchased from Chemical Point (Oberhaching, Germany). Mushroom tyrosinase (1000 U/mg), bovine serum albumin (BSA), glutaraldehyde (GA), poly (diallyldimethylammonium chloride) (PDDA, 20% v/v water solution), 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphopholane, chrome (III) acetylacetonate, deuterated chloroform (CDCl₃), ascorbic acid, Bradford reagent, l-tyrosine, para-cresol, tyrosol, 4-hydroxyphenylacetic acid, 3-(4-hydroxyphenyl)propionic acid, catechol, potassium chloride (KCl), and organic solvents were purchased from Sigma–Aldrich (St. Louis, MO, USA), and were used without any further purification. All experiments were done in triplicate using native and immobilized tyrosinase in Phosphate buffer saline (PBS).

Capecchi E., Piccinino D., Delfino I., Bollella P., Antiochia R, & Saladino R. (2018). Functionalized Tyrosinase-Lignin Nanoparticles as Sustainable Catalysts for the Oxidation of Phenols. Nanomaterials, 8(6), 438.

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Quantification of Polyphenol Standards

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Commercial standards of cyanidin-3-O-glucoside chloride, delphindin-3-O-glucoside chloride, malvidin-3-O-glucoside chloride, gallic acid, caffeic acid, ferulic acid, ethyl gallate, taxi Folin, chlorogenic acid, hippuric acid, 3-hydroxyhippuric acid, 4-hydroxybenzaldehyde, isovanillin, p-anisic acid, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, 3-methoxyphenylacetic acid, isovanillic acid, homovanillic acid, 3-hydroxy-4-methoxyphenylpropionic acid, syringic acid, quercetin, myricetin, chlorogenic acid, quercetin-3-O-glucuronide, protocatechuic acid, p-coumaric acid, catechin, epicatechin, 4-methoxyquercetin, and quercetin-3-O-glucoside as well as sodium carbonate and Folin and Ciocalteu’s reagent (2N) were purchased from Sigma-Aldrich (St. Louis, MO, USA). caffeic acid glucuronide was supplied by Synthose (Concord, Ontario, Canada). LC-MS grade solvents, including methanol, water, ACN, and formic acid as well as trace metal grade concentrated nitric acid were purchased from Thermo Fisher Scientific (Waltham, MA, USA). ⁴⁵Ca was purchased from PerkinElmer (Waltham, MA, USA). EcoLite (+) scintillation cocktail was purchased from MP Biomedicals (Santa Ana, CA, USA).

Cladis D.P., Debelo H., Lachcik P.J., Ferruzzi M.G, & Weaver C.M. (2020). INCREASING DOSES OF BLUEBERRY POLYPHENOLS ALTERS COLONIC METABOLISM AND CALCIUM ABSORPTION IN OVARIECTOMIZED RATS. Molecular nutrition & food research, 64(12), e2000031.

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Quantitative Analysis of Blueberry Polyphenols

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Commercial standards of cyanidin-3-O-glucoside chloride, malvidin-3-O-glucoside chloride, peonidin-3-O-glucoside chloride, petunidin-3-O-glucoside chloride, gallic acid, caffeic acid, ferulic acid, ethyl gallate, taxifolin, chlorogenic acid, 4-hydroxybenzoic acid, 3-hydroxybenzaldehyde, hippuric acid, 3-hydroxyhippuric acid, isovanillin, 4-hydroxyphenylacetic acid, 3-hydroxyphenylpropionic acid, 3-methoxyphenylacetic acid, vanillic acid, homovanillic acid, syringic acid, quercetin, myricetin, quercetin-3-O-glucuronide, 4-methoxyquerceting, p-coumaric acid, epicatechin, kaempferol, and quercetin-3-O-rutinoside as well as sodium carbonate and Folin and Ciocalteu’s reagent (2N) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Extraction and LC-MS grade solvents, including methanol, water, acetonitrile, hexanes, and formic acid were purchased from Thermo Fisher Scientific (Waltham, MA, USA). VitaBlue Pure American Blueberry Extract was obtained from FutureCeuticals (Momence, IL, USA); lyophilized composite wild blueberry (Vaccinium angustifolium) powder was obtained from the Wild Blueberry Association of North America (Old Towne, ME, USA).

Cladis D.P., Simpson A.M., Cooper K.J., Nakatsu C.H., Ferruzzi M.G, & Weaver C.M. (2021). BLUEBERRY POLYPHENOLS ALTER GUT MICROBIOTA & PHENOLIC METABOLISM IN RATS. Food & function, 12(6), 2442-2456.

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UHPLC-MS Analysis of Tea Polyphenols

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Theaflavin-3,3′-digallate (TFDG) and
theaflavin (TF), both with purity of 98%, were purchased from Chromadex
(Santa Ana, CA, USA). Epicatechin (EC), epigallocatechin (EGC), epicatechin
gallate (ECG), epigallocatechin gallate (EGCG), gallic acid, pyrogallol,
4-hydroxybenzoic acid, 4-hydroxyphenylacetic acid, 4-phenylbutyric
acid, 5-(4′-hydroxyphenyl)valeric acid, all with purities of
at least 98%, were purchased from Sigma Aldrich (St. Louis, MO, USA).
Ultra-high performance liquid chromatography/mass spectrometry (UHPLC-MS)
grade acetonitrile (ACN), ACN with 0.1% (v/v) formic acid, and water
with 0.1% (v/v) formic acid were purchased from Biosolve (Valkenswaard,
The Netherlands). Water for other purposes than UHPLC-MS was prepared
using a Milli-Q water purification system (Millipore, Billerica, MA,
USA).

Liu Z., de Bruijn W.J., Bruins M.E, & Vincken J.P. (2020). Microbial Metabolism of Theaflavin-3,3′-digallate and Its Gut Microbiota Composition Modulatory Effects. Journal of Agricultural and Food Chemistry, 69(1), 232-245.

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Quantification of Polyphenol Metabolites

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Ascorbic, 5-caffeoylquinic acid, 3′,4′-dihydroxycinnamic acid, 4′-hydroxy-3′-methoxycinnamic acid, 4′-hydroxycinnamic acid; hippuric acid, 3-(3′,4′-dihydroxyphenyl)propanoic acid, 3-(4′-hydroxy-3′-methoxyphenyl)propanoic acid, 3-(4′-hydroxyphenyl)propanoic acid, 3-(3′-hydroxyphenyl)propanoic acid, 3′,4′-dihydroxyphenylacetic acid, 4′-hydroxy-3′-methoxyphenylacetic acid, 4′-hydroxyphenylacetic acid, 3′-hydroxyphenylacetic acid, 3,4-dihydroxybenzoic acid, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxybenzoic acid, and 3-hydroxybenzoic acid were purchased from Sigma-Aldrich (Madrid, Spain). 3,5-dicaffeoylquinic acid was purchased from PhytoLab (Vestenbergsgreuth, Germany). HPLC-grade solvents were acquired from Panreac (Madrid, Spain). Ultrapure water from MilliQ system (Millipore, Bedford, MA, USA) was used throughout the experiment.

Seguido M.Á., Tarradas R.M., González-Rámila S., García-Cordero J., Sarriá B., Bravo-Clemente L, & Mateos R. (2022). Sustained Consumption of a Decaffeinated Green Coffee Nutraceutical Has Limited Effects on Phenolic Metabolism and Bioavailability in Overweight/Obese Subjects. Nutrients, 14(12), 2445.

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Potassium Ferrate and Oxidative Reactions

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Potassium ferrate (K 2 FeO 4 ), pure (98%) and in the form of mixture (20%), were purchased from Santa Cruz Biotechnology and NanoIron (Czech Republic), respectively. Hydrogen peroxide (H 2 O 2 , 30% in water), Lascorbic acid (AA, reagent grade), Ethylenediamine-N,N'-disuccinic acid trisodium salt solution (EDDS, 35% in water), bisphenol A (BPA, 99%), 3-(2pyridyl)-5,6-diphenyl-1,2,4-triazine-4',4''disulfonic acid sodium salt (ferrozine, 97%), 4-hydroxyphenylacetic acid (HPAA, 98%), Ethylenediaminetetraacetic disodium salt (EDTA, 99%), peroxidase from horseradish (POD) and 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) were supplied by Sigma-Aldrich. The chemicals were used without further purification and the solutions were prepared with ultra-pure water (milli-Q system from Millipore; 18.2 MΩ cm) except when it is specified. The pH of the solution was adjusted with perchloric acid (HClO 4 ) when necessary. Ferric oxide/hydroxide powder including hematite (Fe 2 O 3 ) and goethite (FeOOH) were obtained also from Sigma-Aldrich.

Monfort O., Voyard G., Brigante M, & Mailhot G. (2020). Innovative depollution treatment using multi-valent iron species: from fundamental study to application in municipal wastewater. Environmental science and pollution research international, 27(16).

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