HA (Mw 1 630 000), 3-(3,4-dihydroxyphenyl)propionic acid, EDC and DA were purchased from Sigma-Aldrich. CHI (Mw 200 000–300 000) was received as a gift from Zhejiang Aoxing Biotechnology Co., Ltd. (China). Di-sodium hydrogen phosphate (Na2HPO4·12H2O), sodium phosphate monobasic dihydrate (NaH2PO4·2H2O), sodium sulfate (Na2SO4) and sodium hydroxide (NaOH) were purchased from Beijing Chemical Works (China). Ferric chloride (FeCl3) was purchased from Tianjin Huadong Products (China). Sodium chloride (NaCl) was purchased from Tianjin DingShengXin Chemical Industry Co., Ltd. (China). Potassium chloride (KCl) was purchased from Tianjin DaMao Chemical Reagent Factory (China). The dialysis bag (MW 8000–14 000) was purchased from Beijing DingGuo ChangSheng Biotechnology Co., Ltd. (China). All of the chemicals were used as received without further purification. Deionized water was used in all experiments.
3 3 4 dihydroxyphenyl propionic acid
Manufactured by Merck Group
Sourced in United States
3-(3,4-dihydroxyphenyl)propionic acid is a chemical compound. It is a phenolic acid with the molecular formula C9H10O3.
Automatically generated - may contain errors
Lab products found in correlation
4 hydroxybenzoic acid, by Merck Group (5 mentions)
3 4 dihydroxyphenylacetic acid, by Merck Group (3 mentions)
5 4 hydroxyphenyl valeric acid, by Merck Group (3 mentions)
3 4 hydroxyphenyl propionic acid, by Merck Group (3 mentions)
3 3 hydroxyphenyl propionic acid, by Merck Group (3 mentions)
Protocatechuic acid, by Merck Group (3 mentions)
Procyanidin b2, by Merck Group (2 mentions)
Epicatechin, by Merck Group (2 mentions)
4 phenylbutyric acid, by Merck Group (2 mentions)
Milli q water purification system, by Merck Group (2 mentions)
Gallic acid, by Merck Group (2 mentions)
Benzoic acid, by Merck Group (2 mentions)
Pyrogallol, by Merck Group (2 mentions)
Formic acid, by Biosolve (2 mentions)
4 hydroxyphenylacetic acid, by Merck Group (2 mentions)
Epigallocatechin gallate (egcg), by Merck Group (2 mentions)
Sodium sulfate na2so4, by Beijing Chemical Works (1 mentions)
Sodium hydroxide (naoh), by Beijing Chemical Works (1 mentions)
Formic acid, by Thermo Fisher Scientific (1 mentions)
Procyanidin a2, by Extrasynthese (1 mentions)
8 protocols using 3 3 4 dihydroxyphenyl propionic acid
1
Synthesis of HA-based Composite Hydrogel
2
Chromatography of Polyphenol Standards
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Chromatography
standards of (−)-epicatechin,
procyanidin B2, 3-hydroxyphenylacetic acid (HPA), 3,4-dihydroxyphenylacetic
acid (34PA), and 3-(3,4-dihydroxyphenyl)propionic acid (34PP) were
acquired from Sigma-Aldrich (St. Louis, MO). Standards of 3-(3-hydroxyphenyl)propionic
acid (HPP), 3,4-dihydroxybenzoic acid (34BA), and 3-hydroxybenzoic
acid (HBA) were acquired from Alfa Aesar (Tewksbury, MA). 5-(3′,4′-Dihydroxyphenyl)-g-valerolactone (34PV) was acquired from Toronto Chemicals
(North York, ON, Canada). Procyanidin A2 was purchased from Extrasynthese
(Lyon, France). LC-MS-grade mobile phases were also from Sigma-Aldrich,
and formic acid was from Fisher Scientific (Hampton, NH).
standards of (−)-epicatechin,
procyanidin B2, 3-hydroxyphenylacetic acid (HPA), 3,4-dihydroxyphenylacetic
acid (34PA), and 3-(3,4-dihydroxyphenyl)propionic acid (34PP) were
acquired from Sigma-Aldrich (St. Louis, MO). Standards of 3-(3-hydroxyphenyl)propionic
acid (HPP), 3,4-dihydroxybenzoic acid (34BA), and 3-hydroxybenzoic
acid (HBA) were acquired from Alfa Aesar (Tewksbury, MA). 5-(3′,4′-Dihydroxyphenyl)-g-valerolactone (34PV) was acquired from Toronto Chemicals
(North York, ON, Canada). Procyanidin A2 was purchased from Extrasynthese
(Lyon, France). LC-MS-grade mobile phases were also from Sigma-Aldrich,
and formic acid was from Fisher Scientific (Hampton, NH).
3
Analytical Procedures for Grape Polyphenols
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Grape Seed Polyphenol Extract (GSPE; MegaNatural®-BP Polyphenolics, Warehouse, UPC: 603573579173), Concord Grape Juice (CGJ; Welch Foods, Concord MA), and Resveratrol (RSV; ChromaDex, Irvine CA) were obtained commercially. Malvidin-glucoside, delphinidin-glucoside, quercetin-glucuronide, and cyanidin-glucoside (Extrasynthesis, Genay Cedex, France); 3-hydroxybenzoic acid, 3-(3′-hydroxyphenyl)propionic acid 3-hydroxyphenylacetic acid, 3-(3′, 4′-dihydroxyphenyl)propionic acid, and 5-(4′-hydroxyphenyl)valeric acid (Sigma-Aldrich, St. Louis MO) were obtained commercially and were analyzed by LC-MS and archived as previously reported in compliance with NCCIH Product Integrity guidelines75 (link),76 (link). Unless specified otherwise, cell culture reagents were obtained from ThermoFisher Scientific (Waltham, MA) and antibodies were obtained from Abcam (Cambridge, MA).
4
Analytical Standards Procurement for UHPLC-MS
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Standards
of EC, EGC, ECG, EGCG, gallic acid, pyrogallol, benzoic acid, 4-hydroxybenzoic
acid, 3-(3′,4′-dihydroxyphenyl)propionic acid, 2-(4′-hydroxyphenyl)acetic
acid, 4-phenylbutyric acid, 5-(4′-hydroxyphenyl)valeric acid,
3-(4′-hydroxyphenyl)propionic acid, and 5-phenylvaleric acid
were purchased from Sigma-Aldrich (St. Louis, MO). Acetonitrile (ACN)
was purchased from Biosolve (Valkenswaard, The Netherlands). ULC/MS
grade ACN and water, both with 0.1% (v/v) formic acid, were purchased
from Biosolve (Valkenswaard, The Netherlands). Water for purposes
other than ultrahigh performance liquid chromatography-mass spectrometry
(UHPLC-MS) was prepared using a Milli-Q water purification system
(Millipore, Billerica, MA).
of EC, EGC, ECG, EGCG, gallic acid, pyrogallol, benzoic acid, 4-hydroxybenzoic
acid, 3-(3′,4′-dihydroxyphenyl)propionic acid, 2-(4′-hydroxyphenyl)acetic
acid, 4-phenylbutyric acid, 5-(4′-hydroxyphenyl)valeric acid,
3-(4′-hydroxyphenyl)propionic acid, and 5-phenylvaleric acid
were purchased from Sigma-Aldrich (St. Louis, MO). Acetonitrile (ACN)
was purchased from Biosolve (Valkenswaard, The Netherlands). ULC/MS
grade ACN and water, both with 0.1% (v/v) formic acid, were purchased
from Biosolve (Valkenswaard, The Netherlands). Water for purposes
other than ultrahigh performance liquid chromatography-mass spectrometry
(UHPLC-MS) was prepared using a Milli-Q water purification system
(Millipore, Billerica, MA).
5
Quantitative Analysis of Polyphenol Standards
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Standards
of epicatechin (EC), epigallocatechin
(EGC), epicatechin gallate (ECG), epigallocatechin gallate (EGCG),
procyanidin B2 (PCB2), gallic acid, pyrogallol, benzoic acid, 4-hydroxybenzoic
acid, 3-(4′-hydroxyphenyl)propionic acid, 3-(3′-hydroxyphenyl)propionic
acid, 3-(3′,4′-dihydroxyphenyl)propionic acid, 4-hydroxyphenylacetic
acid, 4-phenylbutyric acid, 5-(4′-hydroxyphenyl)valeric acid,
and 5-phenylvaleric acid were purchased from Sigma Aldrich (St. Louis,
MO, USA). Ultrahigh-performance liquid chromatography/mass spectrometry
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 delivered by Milli-Q water
purification system (Millipore, Billerica, MA, USA) was used for other
purposes than LC–MS.
of epicatechin (EC), epigallocatechin
(EGC), epicatechin gallate (ECG), epigallocatechin gallate (EGCG),
procyanidin B2 (PCB2), gallic acid, pyrogallol, benzoic acid, 4-hydroxybenzoic
acid, 3-(4′-hydroxyphenyl)propionic acid, 3-(3′-hydroxyphenyl)propionic
acid, 3-(3′,4′-dihydroxyphenyl)propionic acid, 4-hydroxyphenylacetic
acid, 4-phenylbutyric acid, 5-(4′-hydroxyphenyl)valeric acid,
and 5-phenylvaleric acid were purchased from Sigma Aldrich (St. Louis,
MO, USA). Ultrahigh-performance liquid chromatography/mass spectrometry
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 delivered by Milli-Q water
purification system (Millipore, Billerica, MA, USA) was used for other
purposes than LC–MS.
6
Characterization of Soluble Cocoa Products
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The commercialized soluble cocoa products used in the study were provided by Idilia Foods (previous company name: Nutrexpa S.L.), one being a conventional soluble cocoa product, labeled as CC, and the other a flavanol-rich soluble cocoa product, labeled as CC-PP. All solvents and reagents were of analytical grade unless otherwise stated. Ascorbic acid, epicatechin, catechin, procyanidin B1, 3-(3,4-dihydroxyphenyl)propionic acid, 3-(4-hydroxyphenyl)propionic acid, 3-(4-hydroxy-3-methoxyphenyl)propionic acid, 3,4-dihydroxyphenylacetic acid, 4-hydroxyphenylacetic acid, 4-hydroxy-3-methoxyphenylacetic acid, protocatechuic acid, 4-hydroxybenzoic acid and ferulic acid were from Sigma-Aldrich (Madrid, Spain). Procyanidin B2 and epicatechin-3-gallate were acquired from Extransynthese Genay Cedex (France). Methanol, formic acid, and acetonitrile (high-performance liquid chromatography (HPLC) grade) were acquired from Panreac (Madrid, Spain).
7
Characterization of Phenolic Compounds
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Sodium hydroxide, citric acid, trans-ferulic acid, trans-isoferulic acid, sinapic acid, caffeic acid, 4-hydroxybenzoic acid, 3’-coumaric acid, 4’-coumaric acid, vanillic acid (3-methoxy-4-hydroxybenzoic acid), protocatechuic acid (3,4-dihydroxybenzoic acid), 3’,4’-dihydroxyphenylacetic acid, 3-(3’-hydroxyphenyl)propionic acid, 3-(4’-hydroxyphenyl)propionic acid, 3-(3’,4’-dihydroxyphenyl)propionic acid (aka dihydrocaffeic acid), 3-(3’,5’-dihydroxyphenyl)propionic acid, 3-(3’-methoxy-4’-hydroxyphenyl)propionic acid (aka dihydroferulic acid), and hippuric acid were purchased from Sigma-Aldrich (St. Louis, MO, USA) as were secoisolariciresinol, enterolactone and enterodiol. Homovanillic acid (3’-methoxy-4’-hydroxyphenylacetic acid) was purchased from Extrasynthese (Genay Cedex, France). Ferulic acid-4’-O-sulphate disodium salt, isoferulic acid-3’-O-β-D-glucuronide, and dihydrocaffeic acid-3’-O-sulphate sodium salt were purchased from Toronto Research Chemical, (Toronto, Canada). Daidzein was purchased in part from AASC. Ltd (Southampton, UK) and in part provided by Prof. Alan Crozier (Department of Nutrition, University of California, Davis, CA, USA).
8
Characterization of Phenolic Compounds
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Chlorogenic acid (99%), quercetin (99%), rutin (97%), protocatechuic acid (97%), 3-(3,4dihydroxyphenyl) propionic acid (98%), and 3-(3-hydroxyphenyl) propionic acid (98%) were obtained from Sigma-Aldrich, while 4-hydroxy-benzoic acid (99%) from Sigma-Aldrich Chemie GmbH.
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