{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T20:05:37Z","timestamp":1791057937400,"version":"4.1.0"},"reference-count":69,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2020,3,20]],"date-time":"2020-03-20T00:00:00Z","timestamp":1584662400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002850","name":"Fondo Nacional de Desarrollo Cient\u00edfico y Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["3160399; 11170142; 1180571"],"award-info":[{"award-number":["3160399; 11170142; 1180571"]}],"id":[{"id":"10.13039\/501100002850","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Powered@NLHPC","award":["ECM-02"],"award-info":[{"award-number":["ECM-02"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Biomolecules"],"abstract":"<jats:p>Glycerol is a co-solvent for water extraction that has been shown to be highly effective for obtaining polyphenol extracts under atmospheric conditions. However, its efficacy under subcritical conditions has not yet been studied. We assessed different water-glycerol mixtures (15%, 32.5%, and 50%) in a hot pressurized liquid extraction system (HPLE: 10 MPa) at 90 \u00b0C, 120 \u00b0C, and 150 \u00b0C to obtain extracts of low molecular weight polyphenols from Carm\u00e9n\u00e8re grape pomace. Under the same extraction conditions, glycerol as a co-solvent achieved significantly higher yields in polyphenols than ethanol. Optimal extraction conditions were 150 \u00b0C, with 32.5% glycerol for flavonols and 50% for flavanols, stilbenes, and phenolic acids. Considering gallic acid as a model molecule, computational chemistry calculations were applied to explain some unusual extraction outcomes. Furthermore, glycerol, methanol, ethanol, and ethylene glycol were studied to establish an incipient structure\u2013property relationship. The high extraction yields of gallic acid obtained with water and glycerol solvent mixtures can be explained not only by the additional hydrogen bonds between glycerol and gallic acid as compared with the other alcohols, but also because the third hydroxyl group allows the formation of a three-centered hydrogen bond, which intensifies the strongest glycerol and gallic acid hydrogen bond. The above occurs both in neutral and deprotonated gallic acid. Consequently, glycerol confers to the extraction solvent a higher solvation energy of polyphenols than ethanol.<\/jats:p>","DOI":"10.3390\/biom10030474","type":"journal-article","created":{"date-parts":[[2020,3,20]],"date-time":"2020-03-20T07:29:07Z","timestamp":1584689347000},"page":"474","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":55,"title":["Glycerol as Alternative Co-Solvent for Water Extraction of Polyphenols from Carm\u00e9n\u00e8re Pomace: Hot Pressurized Liquid Extraction and Computational Chemistry Calculations"],"prefix":"10.3390","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3748-0883","authenticated-orcid":false,"given":"Nils Leander","family":"Huam\u00e1n-Castilla","sequence":"first","affiliation":[{"name":"Chemical and Bioprocess Engineering Department, School of Engineering, Pontificia Universidad Cat\u00f3lica de Chile, Vicu\u00f1a Mackenna 4860, P.O. Box 306, Santiago 7820436, Chile"},{"name":"Escuela de Ingenier\u00eda Agroindustrial, Universidad Nacional de Moquegua, Prolongaci\u00f3n calle Ancash s\/n, Moquegua 18001, Peru"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda Salom\u00e9","family":"Mariotti-Celis","sequence":"additional","affiliation":[{"name":"Programa Institucional de Fomento a la Investigaci\u00f3n, Desarrollo e Innovaci\u00f3n, Universidad Tecnol\u00f3gica Metropolitana, Ignacio Valdivieso 2409, P.O. Box 9845, Santiago 8940577, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2959-3164","authenticated-orcid":false,"given":"Maximiliano","family":"Mart\u00ednez-Cifuentes","sequence":"additional","affiliation":[{"name":"Centro Integrativo de Biolog\u00eda y Qu\u00edmica Aplicada (CIBQA), Escuela de Tecnolog\u00eda M\u00e9dica, Facultad de Ciencias de la Salud, Universidad Bernardo O\u2019Higgins, General Gana 1702, Santiago 8370993, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1278-7782","authenticated-orcid":false,"given":"Jos\u00e9 Ricardo","family":"P\u00e9rez-Correa","sequence":"additional","affiliation":[{"name":"Chemical and Bioprocess Engineering Department, School of Engineering, Pontificia Universidad Cat\u00f3lica de Chile, Vicu\u00f1a Mackenna 4860, P.O. Box 306, Santiago 7820436, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,3,20]]},"reference":[{"key":"ref_1","unstructured":"ODEPA (2019, August 20). Informe Ejecutivo Producci\u00f3n de Vinos. Available online: https:\/\/www.odepa.gob.cl\/publicaciones\/boletines\/boletin-del-vino-agosto-de-2019."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3675","DOI":"10.1021\/jf063232b","article-title":"Characterization of Vitis vinifera L. Cv. Carm\u00e9n\u00e8re Grape and Wine Proanthocyanidins","volume":"55","author":"Fernandez","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","first-page":"176","article-title":"Polyphenols of Carm\u00e9n\u00e8re Grapes","volume":"14","year":"2017","journal-title":"Mini-Reviews Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"9815","DOI":"10.1021\/jf203003c","article-title":"Varietal Differences among the Phenolic Profiles and Antioxidant Activities of Seven Table Grape Cultivars Grown in the South of Italy Based on Chemometrics","volume":"59","author":"Baiano","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1111\/j.1365-2621.2012.03197.x","article-title":"Functional components of grape pomace: Their composition, biological properties and potential applications","volume":"48","author":"Yu","year":"2012","journal-title":"Int. J. Food Sci. Technol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1016\/j.indcrop.2015.05.055","article-title":"Valorization of grape pomace: Extraction of bioactive phenolics with antioxidant properties","volume":"74","author":"Tournour","year":"2015","journal-title":"Ind. Crop. Prod."},{"key":"ref_7","first-page":"113","article-title":"Precipitation of low molecular weight phenolic compounds of grape seeds cv. Carm\u00e9n\u00e8re (Vitis vinifera L.) by whole saliva","volume":"232","year":"2010","journal-title":"Eur. Food Res. Technol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2211","DOI":"10.1007\/s00217-017-2923-1","article-title":"Valorization of Lagrein grape pomace as a source of phenolic compounds: Analysis of the contents of anthocyanins, flavanols and antioxidant activity","volume":"243","author":"Valls","year":"2017","journal-title":"Eur. Food Res. Technol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"581","DOI":"10.1016\/j.wasman.2017.07.017","article-title":"Towards integral utilization of grape pomace from winemaking process: A review","volume":"68","author":"Beres","year":"2017","journal-title":"Waste Manag."},{"key":"ref_10","unstructured":"(2019, July 10). Grand View Research Polyphenols Market Size, Share & Trends Analysis Report By Product (Grape Seed, Green Tea, Cocoa), By Application (Beverages, Food, Feed, Dietary Supplements, Cosmetics), And Segment Forecasts, 2019\u20132025. Available online: https:\/\/www.grandviewresearch.com\/industry-analysis\/polyphenols-market-analysis."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1089\/109662003772519831","article-title":"Polyphenolics in Grape Seeds\u2014Biochemistry and Functionality","volume":"6","author":"Shi","year":"2003","journal-title":"J. Med. Food"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Koteswari, L.L., Kumari, S., Kumar, A.B., and Malla, R.R. (2019). A comparative anticancer study on procyanidin C1 against receptor positive and receptor negative breast cancer. Nat. Prod. Res., 1\u20138.","DOI":"10.1080\/14786419.2018.1557173"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Mlcek, J., Jurikova, T., Skrovankova, S., and Sochor, J. (2016). Quercetin and Its Anti-Allergic Immune Response. Molecules, 21.","DOI":"10.3390\/molecules21050623"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1016\/S0278-6915(99)00031-9","article-title":"Inhibition of Eleven Mutagens by Various Tea Extracts, (\u2212)Epigallocatechin-3-gallate, Gallic Acid and Caffeine","volume":"37","author":"Hour","year":"1999","journal-title":"Food Chem. Toxicol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1016\/S0308-8146(02)00279-0","article-title":"Antioxidant and antimutagenic activities of pomegranate peel extracts","volume":"80","author":"Negi","year":"2003","journal-title":"Food Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2467","DOI":"10.1021\/acs.jcim.8b00981","article-title":"Discovery of Novel Potential Human Targets of Resveratrol by Inverse Molecular Docking","volume":"59","author":"Kores","year":"2019","journal-title":"J. Chem. Inf. Model."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Vang, O., Ahmad, N., Baile, C.A., Baur, J., Brown, K., Csiszar, A., Das, D.K., Delmas, M., Gottfried, C., and Lin, H.-Y. (2011). What Is New for an Old Molecule? Systematic Review and Recommendations on the Use of Resveratrol. PLOS ONE, 6.","DOI":"10.1371\/journal.pone.0019881"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"423","DOI":"10.2174\/138945006776359331","article-title":"Resveratrol as a chemopreventive agent: A promising molecule for fighting cancer","volume":"7","author":"Delmas","year":"2006","journal-title":"Curr. Drug Targets"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1261","DOI":"10.1007\/s00204-016-1784-x","article-title":"Sirtuin 1-dependent resveratrol cytotoxicity and pro-differentiation activity on breast cancer cells","volume":"91","author":"Deus","year":"2016","journal-title":"Arch. Toxicol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1155","DOI":"10.1016\/j.bbadis.2014.10.016","article-title":"Preclinical and clinical evidence for the role of resveratrol in the treatment of cardiovascular diseases","volume":"1852","author":"Zordoky","year":"2015","journal-title":"Biochim. et Biophys. Acta (BBA) - Mol. Basis Dis."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1111\/j.1747-0285.2009.00781.x","article-title":"Histone Deacetylase, Inhibition Activity and Molecular Docking of (e)-Resveratrol: Its Therapeutic Potential in Spinal Muscular Atrophy","volume":"73","author":"Bora","year":"2009","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.neuint.2016.12.012","article-title":"Resveratrol suppresses neuroinflammation in the experimental paradigm of autism spectrum disorders","volume":"103","author":"Bhandari","year":"2017","journal-title":"Neurochem. Int."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"27","DOI":"10.2174\/138161212798919075","article-title":"Resveratrol, a Neuroprotective Supplement for Alzheimer\u2019s Disease","volume":"18","author":"Li","year":"2012","journal-title":"Curr. Pharm. Des."},{"key":"ref_24","first-page":"77","article-title":"Grape and wine phenolics: Observations and recent findings","volume":"35","year":"2008","journal-title":"Ciencia e investigaci\u00f3n agraria"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"15504","DOI":"10.1021\/acssuschemeng.9b03208","article-title":"Valorization of Soy Whey Wastewater: How Epigallocatechin-3-gallate Regulates Protein Precipitation","volume":"7","author":"Xu","year":"2019","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1155\/2018\/7830546","article-title":"Phenolic Acid Content and Antioxidant Properties of Extruded Corn Snacks Enriched with Kale","volume":"2018","author":"Kasprzak","year":"2018","journal-title":"J. Anal. Methods Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"10980","DOI":"10.1039\/C8RA01213J","article-title":"Quercetin spectrofluorometric quantification in aqueous media using different surfactants as fluorescence promoters","volume":"8","author":"Romo","year":"2018","journal-title":"RSC Adv."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3198","DOI":"10.1039\/C7FO00508C","article-title":"Encapsulation of flavonoids in liposomal delivery systems: The case of quercetin, kaempferol and luteolin","volume":"8","author":"Huang","year":"2017","journal-title":"Food Funct."},{"key":"ref_29","first-page":"3","article-title":"Applications of Wine Pomace in the Food Industry: Approaches and Functions","volume":"16","year":"2016","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"626","DOI":"10.4161\/psb.3.9.6686","article-title":"Transport and accumulation of flavonoids in grapevine (Vitis vinifera L.)","volume":"3","author":"Braidot","year":"2008","journal-title":"Plant Signal. Behav."},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Gao, Y., Zietsman, A., Vivier, M.A., and Moore, J. (2019). Deconstructing Wine Grape Cell Walls with Enzymes During Winemaking: New Insights from Glycan Microarray Technology. Molecules, 24.","DOI":"10.3390\/molecules24010165"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1111\/1541-4337.12253","article-title":"Green Extraction Methods for Polyphenols from Plant Matrices and Their Byproducts: A Review","volume":"16","author":"Ameer","year":"2017","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Manousaki, A., Jancheva, M., Grigorakis, S., and Makris, D.P. (2016). Extraction of Antioxidant Phenolics from Agri-Food Waste Biomass Using a Newly Designed Glycerol-Based Natural Low-Transition Temperature Mixture: A Comparison with Conventional Eco-Friendly Solvents. Recycling, 1.","DOI":"10.3390\/recycling1010194"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Putnik, P., Lorenzo, J.M., Barba, F.J., Roohinejad, S., Jambrak, A.R., Granato, D., Montesano, D., and Kova\u010devi\u0107, D.B. (2018). Novel Food Processing and Extraction Technologies of High-Added Value Compounds from Plant Materials. Foods, 7.","DOI":"10.3390\/foods7070106"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"162","DOI":"10.1016\/j.foodchem.2016.03.084","article-title":"Influence of solvents on the composition of condensed tannins in grape pomace seed extracts","volume":"207","author":"Bosso","year":"2016","journal-title":"Food Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"296","DOI":"10.1016\/j.jfda.2013.11.001","article-title":"Effect of extraction solvent on total phenol content, total flavonoid content, and antioxidant activity of Limnophila aromatica","volume":"22","author":"Do","year":"2014","journal-title":"J. Food Drug Anal."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.seppur.2014.03.010","article-title":"Optimisation and comparative kinetics study of polyphenol extraction from olive leaves (Olea europaea) using heated water\/glycerol mixtures","volume":"128","author":"Apostolakis","year":"2014","journal-title":"Sep. Purif. Technol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"176","DOI":"10.1080\/10826068.2015.1015562","article-title":"Optimization of polyphenol extraction from red grape pomace using aqueous glycerol\/tartaric acid mixtures and response surface methodology","volume":"46","author":"Makris","year":"2016","journal-title":"Prep. Biochem. Biotechnol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3939","DOI":"10.1007\/s13197-016-2381-y","article-title":"Optimization of a green extraction method for the recovery of polyphenols from olive leaf using cyclodextrins and glycerin as co-solvents","volume":"53","author":"Mourtzinos","year":"2016","journal-title":"J. Food Sci. Technol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"462","DOI":"10.1016\/j.seppur.2015.06.017","article-title":"Extraction optimisation using water\/glycerol for the efficient recovery of polyphenolic antioxidants from two Artemisia species","volume":"149","author":"Shehata","year":"2015","journal-title":"Sep. Purif. Technol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1016\/j.rser.2013.06.035","article-title":"Glycerol production and its applications as a raw material: A review","volume":"27","author":"Tan","year":"2013","journal-title":"Renew. Sustain. Energy Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1391","DOI":"10.1039\/c0gc00797h","article-title":"Searching for green solvents","volume":"13","author":"Jessop","year":"2011","journal-title":"Green Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1245","DOI":"10.1039\/c2gc16670d","article-title":"Solvatochromic parameters for solvents of interest in green chemistry","volume":"14","author":"Jessop","year":"2012","journal-title":"Green Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.trac.2015.02.022","article-title":"Pressurized hot water extraction of bioactives","volume":"71","author":"Plaza","year":"2015","journal-title":"Trends Anal. Chem."},{"key":"ref_45","first-page":"83","article-title":"Pressurized Liquid Extraction of Organic Contaminants in Environmental and Food Samples","volume":"76","year":"2017","journal-title":"Comprehensive Analytical Chemistry"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1016\/j.foodchem.2014.08.094","article-title":"Characterization of pressurized hot water extracts of grape pomace: Chemical and biological antioxidant activity","volume":"171","author":"Vergara","year":"2015","journal-title":"Food Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"6929","DOI":"10.1021\/jf4010143","article-title":"Effect of Pressurized Hot Water Extraction on Antioxidants from Grape Pomace before and after Enological Fermentation","volume":"61","author":"Bulnes","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"2610","DOI":"10.1016\/j.jiec.2013.10.048","article-title":"Effects of repeated treatment on the properties of rice stem extract using subcritical water, ethanol, and their mixture","volume":"20","author":"Tangkhavanich","year":"2014","journal-title":"J. Ind. Eng. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2862","DOI":"10.1021\/jf904087n","article-title":"Subcritical Solvent Extraction of Anthocyanins from Dried Red Grape Pomace","volume":"58","author":"Monrad","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"9686","DOI":"10.3390\/molecules20069686","article-title":"Green Extraction of Antioxidants from Different Varieties of Red Grape Pomace","volume":"20","author":"Cardoso","year":"2015","journal-title":"Molecules"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"4014","DOI":"10.1021\/jf9028283","article-title":"Subcritical Solvent Extraction of Procyanidins from Dried Red Grape Pomace\u2020","volume":"58","author":"Monrad","year":"2010","journal-title":"J. Agric. Food Chem."},{"key":"ref_52","first-page":"1072","article-title":"Impact of an integrated process of hot pressurised liquid extraction-macroporous resin purification over the polyphenols, hydroxymethylfurfural and reducing sugars content of Vitis vinifera \u2018Carm\u00e9n\u00e8re\u2019 pomace extracts","volume":"53","author":"Pedreschi","year":"2017","journal-title":"Int. J. Food Sci. Technol."},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Huaman-Castilla, N.L., Mart\u00ednez-Cifuentes, M., Camilo, C., Pedreschi, F., Mariotti-Celis, M., and P\u00e9rez-Correa, J.R. (2019). The Impact of Temperature and Ethanol Concentration on the Global Recovery of Specific Polyphenols in an Integrated HPLE\/RP Process on Carm\u00e9n\u00e8re Pomace Extracts. Molecules, 24.","DOI":"10.3390\/molecules24173145"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"22935","DOI":"10.1039\/C4CP02585G","article-title":"Hydrogen bonding, halogen bonding and lithium bonding: An atoms in molecules and natural bond orbital perspective towards conservation of total bond order, inter- and intra-molecular bonding","volume":"16","author":"Shahi","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"9354","DOI":"10.3390\/molecules19079354","article-title":"Intramolecular Hydrogen Bond in Biologically Active o-Carbonyl Hydroquinones","volume":"19","author":"Santos","year":"2014","journal-title":"Molecules"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Mart\u00ednez-Cifuentes, M., Cardona, W., Saitz-Barr\u00eda, C., Weiss-L\u00f3pez, B.E., and Araya-Maturana, R. (2017). A Study about Regioisomeric Hydroquinones with Multiple Intramolecular Hydrogen Bonding. Molecules, 22.","DOI":"10.3390\/molecules22040593"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1021\/cr00088a005","article-title":"Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint","volume":"88","author":"Reed","year":"1988","journal-title":"Chem. Rev."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4230","DOI":"10.1039\/c2ay26093j","article-title":"Rapid determination of ten polyphenols in Kudiezi injection using ultra-performance liquid chromatography-tandem mass spectrometry in multiple reaction monitoring mode","volume":"4","author":"Liu","year":"2012","journal-title":"Anal. Methods"},{"key":"ref_59","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, G.E., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (2009). Gaussian 09, Revision D.01, Gaussian Inc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1016\/j.aca.2005.10.054","article-title":"Recovery of catechins and proanthocyanidins from winery by-products using subcritical water extraction","volume":"563","year":"2006","journal-title":"Anal. Chim. Acta"},{"key":"ref_61","unstructured":"U.S. National Library of Medicine (NIH) (2019, August 18). Flavanols Chemical Structure, Available online: https:\/\/pubchem.ncbi.nlm.nih.gov\/compound\/."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"10625","DOI":"10.1021\/jf902498y","article-title":"The Optimization of Extraction of Antioxidants from Apple Pomace by Pressurized Liquids","volume":"57","author":"Wijngaard","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/j.foodchem.2014.07.047","article-title":"Extraction characteristics of subcritical water depending on the number of hydroxyl group in flavonols","volume":"168","author":"Cheigh","year":"2015","journal-title":"Food Chem."},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Furlan, V., and Bren, U. (2020). Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21030695"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"3279","DOI":"10.1021\/acs.jnatprod.9b00435","article-title":"Tannin Basic Building Blocks as Potential Scavengers of Chemical. Carcinogens: A Computational Study","volume":"82","author":"Hostnik","year":"2019","journal-title":"J. Nat. Prod."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.1021\/acs.jpclett.9b03804","article-title":"Local Acid Strength of Solutions and Its Quantitative Evaluation Using Excess Infrared Nitrile Probes","volume":"11","author":"Xu","year":"2020","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Mart\u00ednez-Cifuentes, M., Monroy-C\u00e1rdenas, M., Millas-Vargas, J.P., Weiss-L\u00f3pez, B.E., and Araya-Maturana, R. (2019). Assessing Parameter Suitability for the Strength Evaluation of Intramolecular Resonance Assisted Hydrogen Bonding in o-Carbonyl Hydroquinones. Molecules, 24.","DOI":"10.3390\/molecules24020280"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/S0003-2670(03)00334-9","article-title":"Spectrophotometric, potentiometric and chromatographic pKa values of polyphenolic acids in water and acetonitrile\u2013water media","volume":"484","author":"Sanli","year":"2003","journal-title":"Anal. Chimica Acta"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1016\/j.molliq.2015.03.055","article-title":"Solvent dependence of protonation equilibria for gallic acid in water and different acetonitrile\u2013water cosolvent systems","volume":"208","author":"Jabbari","year":"2015","journal-title":"J. Mol. Liq."}],"container-title":["Biomolecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2218-273X\/10\/3\/474\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:09:56Z","timestamp":1760173796000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2218-273X\/10\/3\/474"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3,20]]},"references-count":69,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2020,3]]}},"alternative-id":["biom10030474"],"URL":"https:\/\/doi.org\/10.3390\/biom10030474","relation":{},"ISSN":["2218-273X"],"issn-type":[{"value":"2218-273X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,3,20]]}}}