Hydroxytyrosol

Manufactured by Extrasynthese

Sourced in France, Switzerland, Germany

Hydroxytyrosol is a natural phenolic compound found in olive oil. It is a powerful antioxidant that helps protect cells from oxidative stress. Hydroxytyrosol can be used in various applications, such as dietary supplements and cosmetic products.

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Lab products found in correlation

Oleuropein, by Extrasynthese (16 mentions) Tyrosol, by Extrasynthese (14 mentions) Pinoresinol, by Merck Group (10 mentions) Apigenin, by Extrasynthese (9 mentions) Luteolin, by Extrasynthese (8 mentions) P coumaric acid, by Merck Group (7 mentions) Milli q purification system, by Merck Group (7 mentions) Gallic acid, by Merck Group (7 mentions) Caffeic acid, by Merck Group (7 mentions) Methanol, by Merck Group (6 mentions) Acetonitrile, by Merck Group (6 mentions) 3 4 dihydroxyphenylglycol, by Merck Group (6 mentions) Hexane, by Merck Group (6 mentions) Oleuropein, by Merck Group (6 mentions) Oleocanthal, by Merck Group (6 mentions) Milli q system, by Merck Group (5 mentions) Formic acid, by Merck Group (5 mentions) 2 2 diphenyl 1 picrylhydrazyl (dpph), by Merck Group (5 mentions) Quercetin, by Merck Group (5 mentions) Epicatechin, by Merck Group (5 mentions)

43 protocols using hydroxytyrosol

Quantification of Olive Oil Phenolics

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Formic acid, sulfuric acid (95.0%–98.0%), m ethanol and acetonitrile of HPLC grade, m ethanol and ethanol of analytical grade were obtained from Sigma Aldrich (Steinheim, Germany). Ultrapure water was obtained from the Milli-Q-system (Millipore SA, Molsheim, France). Tyrosol (≥98%), hydroxyTyrosol (≥98%) and oleuropein (≥98%) were purchased from Extrasynthèse (Genay, France).
Standard stock solutions were prepared as follows: oleuropein 175 mg/L in MeOH:H₂O 80:20, hydroxyTyrosol 1500 mg/L in MeOH:H₂O 80:20 v/v and Tyrosol 1,500 mg/L in MeOH:H₂O 80:20. These stock solutions were stored at −18 °C and warmed at room temperature when used for preparing the diluted solutions for calibration. These latter were prepared daily for Tyrosol and hydroxyTyrosol, starting from different aliquots of stock solutions for obtaining diluted solutions in the range of 1–150 mg/L. This working range was selected based on the typical contents of Tyrosol and hydroxyTyrosol that can be expected to be found in virgin olive oils.

Bellumori M., Cecchi L., Innocenti M., Clodoveo M.L., Corbo F, & Mulinacci N. (2019). The EFSA Health Claim on Olive Oil Polyphenols: Acid Hydrolysis Validation and Total Hydroxytyrosol and Tyrosol Determination in Italian Virgin Olive Oils. Molecules, 24(11), 2179.

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Phytochemical Standards Characterization

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3,4-dihydroxyphenylglycol was obtained from Sigma-Aldrich (Deisenhofer, Germany). Tyrosol was obtained from Fluka (Buchs, Switzerland) and hydroxytyrosol was obtained from Extrasynthese (Lyon Nord, Geney, France). Standards of gallic acid (GA), trifluoroacetic acid (TFA), anthrone, glucose, Folin-Ciocalteu’s phenol reagent, and 2,2-diphenyl-1-picrylhydrazyl were purchased from Sigma-Aldrich (Madrid, Spain). Sodium bicarbonate (Na₂CO₃), acetonitrile (HPLC grade, hexane and sulphuric acid (H₂SO₄) were obtained from PanreacQuimica S.A. (Barcelona, Spain).

Fernández-Prior M.Á., Fatuarte J.C., Oria A.B., Viera-Alcaide I., Fernández-Bolaños J, & Rodríguez-Gutiérrez G. (2020). New Liquid Source of Antioxidant Phenolic Compounds in the Olive Oil Industry: Alperujo Water. Foods, 9(7), 962.

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Quantitative Analysis of Phenolic Compounds

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Phenols were quantified using a Hewlett-Packard 1100 liquid chromatography system with a C-18 column (Mediterranea SEA 18, Teknokroma, 250 mm x 4.6 mm, i.d. 5 μm) and diode array detector (DAD, the wavelengths used for quantification were 254, 280, and 340 nm) with Rheodyne injection valves (20 μL loop). The mobile phase A was Milli-Q water acidified with 0.01 % trichloroacetic acid and acetonitrile utilizing the following gradient over a total run time of 55 min: 95 % A initially, 75 % A in 30 min, 50 % A in 45 min, 0 % A in 47 min, 75 % A in 95 min, and 95 % A in 52 min until completion of the run. Quantification was carried out by integration of the peaks at different wavelengths in function of the compounds, with reference to calibrations made using external standards. Hydroxymethylfurfural (HMF), furfural and trichloroacetic acid were obtained from Sigma-Aldrich (Deisenhofer, Germany). Hydroxytyrosol was obtained from Extrasynthese (Lyon Nord, Geney, France). Tyrosol was obtained from Fluka (Buchs, Switzerland). HPLC-grade acetonitrile was purchased from Merck (Darmstadt, Germany) and ultrapure water was obtained using a Milli-Q water system (Millipore, Milford, MA, USA).

Serrano A., Fermoso F.G., Alonso-Fariñas B., Rodríguez-Gutierrez G., Fernandez-Bolaños J, & Borja R. (2017). Phenols recovery after steam explosion of Olive Mill Solid Waste and its influence on a subsequent biomethanization process. Bioresource technology, 243.

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HPLC-Based Quantification of Phenolic Compounds

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To identify the phenolic compounds and determine their contents in the extracts and oil samples, the method of Espínola et al. [23 (link)] was used with minor modifications. A Model 20 series high-performance liquid chromatograph (Shimadzu, Kyoto, Japan) equipped with a BDS Hypersil C18 column (Thermo Scientific, Waltham, MA, USA) was used. The mobile phase was a ternary gradient made up of Milli-Q water with 0.2% ortho-phosphoric acid, methanol, and acetonitrile. The elution flow rate was 1 mL/min. The oven temperature was set at 30 °C, and the injected volume of sample was 20 μL. The UV detector provided a signal at 280 nm. The phenolic compounds were identified and quantified by comparison with analytical standards of hydroxy tyrosol from Extrasynthese (Genay Cedex, France), oleuropein from Fluka (Milan, Italy), and tyrosol, apigenin, apigenin-7-O-glucoside, luteolin-7-O-glucoside, and verbascoside from Sigma-Aldrich (St. Louis, MO, USA). The results are expressed as milligrams of compound per gram of dry extract or per kilogram of oil.

Vidal A.M., Moya M., Alcalá S., Romero I, & Espínola F. (2022). Enrichment of Refined Olive Oils with Phenolic Extracts of Olive Leaf and Exhausted Olive Pomace. Antioxidants, 11(2), 204.

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Quantification of Phytochemical Standards

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Methanol (MeOH) and acetonitrile (AcN) were purchased from Merck (Darmstadt, Germany) and phosphoric acid from Sigma-Aldrich (St. Louis, MO, USA). Standards of apigenin, apigenin-7-O-glucoside, catechin, hydroxy tyrosol, luteolin, luteolin-7-O-glucoside, oleuropein, rutin, tyrosol, and verbascoside were purchased from Extrasynthese (Genay, France). Deionized water was obtained by Siemens UltraClear (Siemens AG, München, Germany).
Multi-element standard solution from Perkin Elmer (NexION Setup Solution, Waltham, MA, USA) was used. Argon used to form plasma for the inductively coupled plasma mass spectrometer (ICP-MS) analysis was of purity 6.0 (Messer, Austria). Acetylene was supplied by Messer (Messer Croatia Plin d.o.o., Zaprešić, Croatia).
Deionized water was obtained by Siemens UltraClear (Siemens AG, München, Germany).

Pasković I., Lukić I., Žurga P., Majetić Germek V., Brkljača M., Koprivnjak O., Major N., Grozić K., Franić M., Ban D., Marcelić Š, & Goreta Ban S. (2020). Temporal Variation of Phenolic and Mineral Composition in Olive Leaves Is Cultivar Dependent. Plants, 9(9), 1099.

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Antioxidant Activity Determination Methods

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Folin–Ciocalteu’s phenol reagent, 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS™), 2,4,6,-tri(2pyridyl)-1,3,5,-triazine (TPTZ), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), orthophosphoric acid and the standard of gallic acid were provided by Sigma-Aldrich (St. Louis, MO, USA). Methanol and acetonitrile of HPLC grade was obtained from Honeywell (Morristown, NJ, USA) and PanReac AppliChem (Barcelona, Spain), respectively. The following standards were obtained from Extrasynthese (Genay, France): hydroxytyrosol, maslinic acid and oleanolic acid. Ultrapure water was obtained using a Milli-Q system (Millipore, Bedford, MA, USA).

Gómez-Cruz I., Contreras M.D., Romero I, & Castro E. (2021). Sequential Extraction of Hydroxytyrosol, Mannitol and Triterpenic Acids Using a Green Optimized Procedure Based on Ultrasound. Antioxidants, 10(11), 1781.

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Bioactive Olive Compound Extraction

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Oleocanthal and oleacein were purchased from PhytoLab GmbH (Vestenbergsgreuth, Germany); oleuropein aglycone from the Toronto Research Chemical Inc. (Ontario, Canada); luteolin and nonadecanoic acid from Sigma-Aldrich (Madrid, Spain); ferulic acid and apigenin from Fluka (Buchs, Switzerland) and hydroxytyrosol from Extrasynthese (Genay, France). Hexane, methanol, acetonitrile were purchased from Sigma-Aldrich, and cicloHexane from Panreac.

López-Yerena A., Ninot A., Lozano-Castellón J., Escribano-Ferrer E., Romero-Aroca A.J., Belaj A., Vallverdú-Queralt A, & Lamuela-Raventós R.M. (2020). Conservation of Native Wild Ivory-White Olives from the MEDES Islands Natural Reserve to Maintain Virgin Olive Oil Diversity. Antioxidants, 9(10), 1009.

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Analysis of Polyphenolic Compounds

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Formic acid and HPLC grade methanol were purchased from VWR Prolabo (Fontenay-sous-Bois, France). Deionized water was obtained from a Milli-Q purification system (Millipore, Molsheim, France). Standard of trans-piceid was purchased from Selleckchem (Houston, TX, USA). Standards of caffeic acid, vanillic acid, gallic acid and ferulic acid were purchased from Fluka (Buchs, Switzerland). Standards of syringic acid, p-coumaric acid, protocatechuic acid, ethyl protocatechuate, tyrosol, tryptophol, tryptophan, trans-resveratrol, quercetin, catechin, epicatechin, epicatechin 3-gallate, taxifolin, oxidized and reduced glutathione were purchased from Sigma-Aldrich (St. Louis, MO, USA), as well as hydrochloric acid, phloroglucinol, L-ascorbic acid, and ammonium formiate. Standards of ethyl gallate, ethyl caffeate, tyrosine, hydroxytyrosol, epigallocatechin, malvidin 3-O-glucoside chloride, and malvidin 3,5-diglucoside chloride were purchased from Extrasynthese (Geney, France). Standards of trans-caftaric acid, quercetin glucoside and procyanidin dimers B1, B2, B3, B4, and trimer C1 were purchased from Phytolab (Vestenbergsgreuth, Germany).

Leborgne C., Lambert M., Ducasse M.A., Meudec E., Verbaere A., Sommerer N., Boulet J.C., Masson G., Mouret J.R, & Cheynier V. (2022). Elucidating the Color of Rosé Wines Using Polyphenol-Targeted Metabolomics. Molecules, 27(4), 1359.

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Comprehensive HPLC Analysis of Plant Metabolites

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HPLC-grade methanol, acetonitrile and formic acid were purchased from Sigma-Aldrich (St. Louis, MO, US). A Milli-Q system from Millipore (Bedford, MA, USA) was used for purifying demineralized water. The PVDF (polyvinylidene fluoride) syringe filters were also supplied by Millipore. The standards used were as follows: citric acid, isocitric acid, mannose, dulcitol, oleuropein, raffinose, stachyose, salidroside, sorbitol, tyrosol and 3,4-dihydroxyphenylglycol purchased from Sigma-Aldrich (St. Louis, MO, US); malic acid, fructose, glucose and sucrose purchased from Carlo Erba (Milan, Italy); succinic acid, galactinol, galactose and lactose purchased from Honeywell Fluka (Milan, Italy); quinic acid purchased from Roth (Karlsruhe, Germany); and hydroxytyrosol and verbascoside purchased from Extrasynthese (Genay Cedex, Lyon, France).

Garcia-Aloy M., Groff N., Masuero D., Nisi M., Franco A., Battelini F., Vrhovsek U, & Mattivi F. (2020). Exploratory Analysis of Commercial Olive-Based Dietary Supplements Using Untargeted and Targeted Metabolomics. Metabolites, 10(12), 516.

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Analytical Characterization of Phenolic Compounds

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Analytical grade reagents of Riedel-deHaen (Germany), Sigma-Aldrich (Germany) and Merck (Germany) were used in the analysis. Caffeic, 4hydroxyphenylacetic, 2, ferulic and gallic acids, hydroxy tyrosol, tyrosol, luteolin, vanillin and pinoresinol standards were products of Extrasynthese (France) and Fluka (Germany). Fatty acid methyl ester (FAME) mixture containing C4-C24 (Supelco #47885-U) was used as a reference standard for GC-FID analysis.

Jolayemi O.S., Tokatli F, & Ozen B. (2016). Effects of malaxation temperature and harvest time on the chemical characteristics of olive oils. Food chemistry, 211.

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