{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T14:22:19Z","timestamp":1791901339220,"version":"4.3.4"},"reference-count":86,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2025,10,24]],"date-time":"2025-10-24T00:00:00Z","timestamp":1761264000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A comprehensive analysis of key findings derived from density functional theory (DFT) studies reveals that current theoretical data on curcumin remain incomplete, underscoring the need for further computational investigation to achieve a more thorough understanding of its chemical and biological reactivity. This study addresses these gaps through four primary objectives: (i) determination of a complete set of thermodynamic descriptors and elucidation of the multi-step anti-radical mechanisms of the neutral, radical, anionic, and radical\u2013anionic forms of curcumin; (ii) calculation of global chemical reactivity descriptors of curcumin in various solvent environments; (iii) theoretical reproduction of experimentally determined pKa values for all active sites within the molecule; and (iv) examination of the effects of dispersion interactions and solvent polarity on the reactivity descriptors of keto\u2013enol forms of curcumin. The results obtained provide enhanced insight into the molecular behavior of curcumin, facilitating improved predictions of its reactivity under diverse conditions. Moreover, the findings indicate a potential structural modification of the keto form of curcumin, involving the attachment of two 4-hydroxy-3-methoxyphenyl-prop-1-en-2-one moieties to the methylene group. The resulting modeled compound, referred to as di-curcumin, exhibits enhanced chemical reactivity and increased anti-radical potential.<\/jats:p>","DOI":"10.3390\/ijms262110374","type":"journal-article","created":{"date-parts":[[2025,10,27]],"date-time":"2025-10-27T00:51:42Z","timestamp":1761526302000},"page":"10374","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Reactivity of Curcumin: Theoretical Insight from a Systematic Density Functional Theory-Based Review"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6217-0158","authenticated-orcid":false,"given":"Marcin","family":"Molski","sequence":"first","affiliation":[{"name":"Department of Quantum Chemistry, Faculty of Chemistry, Adam Mickiewicz University of Pozna\u0144, ul. Uniwersytetu Pozna\u0144skiego 8, 61-614 Pozna\u0144, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,10,24]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5308","DOI":"10.1002\/anie.201107724","article-title":"Curcumin\u2014From Molecule to Biological Function","volume":"51","author":"Esatbeyoglu","year":"2012","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1620","DOI":"10.1021\/acs.jmedchem.6b00975","article-title":"The essential medicinal chemistry of curcumin: Mini-perspective","volume":"60","author":"Nelson","year":"2017","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Kotha, R.R., and Luthria, D.L. (2019). Curcumin: Biological, pharmaceutical, nutraceutical, and analytical aspects. Molecules, 24.","DOI":"10.3390\/molecules24162930"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2889","DOI":"10.1080\/10408398.2015.1077195","article-title":"Curcumin, an active component of turmeric (Curcuma longa), and its effects on health","volume":"57","author":"Kocaadam","year":"2017","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_5","first-page":"550909","article-title":"Turmeric and its major compound curcumin on health: Bioactive effects and safety profiles for food, pharmaceutical, biotechnological and medicinal applications","volume":"11","author":"Rayess","year":"2020","journal-title":"Front. Pharmacol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1377","DOI":"10.1080\/10942912.2022.2082464","article-title":"A Review on selected pharmacological activities of Curcuma longa L","volume":"25","author":"Jyotirmayee","year":"2022","journal-title":"Int. J. Food Prop."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"7606","DOI":"10.1021\/acs.jafc.5b00244","article-title":"Degradation of curcumin: From mechanism to biological implications","volume":"63","author":"Schneider","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"117403","DOI":"10.1016\/j.taap.2025.117403","article-title":"Curcumin induces apoptosis via downregulation of SKP2 and induction of GADD45A\/CDKN1A expression through generation of ROS in cutaneous T-cell lymphoma cells","volume":"501","author":"Kuttikrishnan","year":"2025","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2140","DOI":"10.1080\/10408398.2020.1850417","article-title":"Curcumin, autoimmune and inflammatory diseases: Going beyond conventional Therapy\u2014A systematic review","volume":"62","author":"Marton","year":"2022","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5505","DOI":"10.1007\/s00253-016-7415-x","article-title":"Antibacterial activity of curcumin via apoptosis-like response in Escherichia coli","volume":"100","author":"Yun","year":"2016","journal-title":"Appl. Microbiol. Biotechnol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1016\/j.jtcme.2016.05.005","article-title":"Biological activities of curcuminoids, other biomolecules from turmeric and their Derivatives\u2014A review","volume":"7","author":"Amalraj","year":"2017","journal-title":"J. Tradit. Complement. Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"100384","DOI":"10.1016\/j.jphotochemrev.2020.100384","article-title":"Curcumin as a photosensitizer: From molecular structure to recent advances in antimicrobial photodynamic therapy","volume":"45","author":"Dias","year":"2020","journal-title":"J. Photochem. Photobiol. C Photochem. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1255","DOI":"10.1016\/j.toxrep.2021.06.008","article-title":"Safety assessment of a highly bioavailable curcumin-galactomannoside complex (CurQfen) in healthy volunteers, with a special reference to the recent hepatotoxic reports of curcumin supplements: A 90-Days prospective study","volume":"8","author":"Pancholi","year":"2021","journal-title":"Toxicol. Rep."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"103484","DOI":"10.1016\/j.jddst.2022.103484","article-title":"Exploring Z-Tyr-Phe-OH-Based hydrogels loaded with curcumin for the development of dressings for wound healing","volume":"73","author":"Alves","year":"2022","journal-title":"J. Drug Deliv. Sci. Technol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"117954412094847","DOI":"10.1177\/1179544120948471","article-title":"The efficacy and safety of highly-bioavailable curcumin for treating knee osteoarthritis: A 6-Month open-labeled prospective study","volume":"13","author":"Nakagawa","year":"2020","journal-title":"Clin. Med. Insights Arthritis Musculoskelet. Disord."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"e2301012","DOI":"10.1002\/smll.202301012","article-title":"Development of a ZIF-91-porous-liquid-based composite hydrogel dressing system for diabetic wound healing","volume":"19","author":"Weng","year":"2023","journal-title":"Small"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Kuzminska, J., Szyk, P., Mlynarczyk, D.T., Bakun, P., Muszalska-Kolos, I., Dettlaff, K., Sobczak, A., Goslinski, T., and Jelinska, A. (2024). Curcumin derivatives in medicinal chemistry: Potential applications in cancer treatment. Molecules, 29.","DOI":"10.3390\/molecules29225321"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Raduly, F.M., Raditoiu, V., Raditoiu, A., Nicolae, C.A., Grapin, M., Stan, M.S., Voinea, I.C., Vlasceanu, R.I., Nitu, C.D., and Mihailescu, D.F. (2024). Half-curcuminoids encapsulated in alginate-glucosamine hydrogel matrices as bioactive delivery dystems. Gels, 10.","DOI":"10.3390\/gels10060376"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"41, 9677","DOI":"10.1021\/ja991446m","article-title":"H-Atom transfer is a preferred antioxidant mechanism of curcumin","volume":"121","author":"Jovanovic","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2909","DOI":"10.1021\/ol0262789","article-title":"Theoretical elucidation on the antioxidant mechanism of curcumin: A DFT study","volume":"4","author":"Sun","year":"2002","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1016\/j.saa.2006.08.018","article-title":"Theoretical study on physicochemical properties of curcumin","volume":"67","author":"Shen","year":"2007","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1007\/s00894-022-05056-4","article-title":"Antiradical properties of curcumin, caffeic acid phenethyl ester, and chicoric acid: A DFT study","volume":"28","author":"Manzanilla","year":"2022","journal-title":"J. Mol. Model."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"131499","DOI":"10.1016\/j.foodchem.2021.131499","article-title":"Curcumin analogues with improved antioxidant properties: A theoretical exploration","volume":"373","author":"Purushothaman","year":"2022","journal-title":"Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"589","DOI":"10.1080\/08927022.2023.2178236","article-title":"A DFT study on the scavenging activity of curcumin toward methyl and ethyl radicals","volume":"49","author":"Biswas","year":"2023","journal-title":"Mol. Simul."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1016\/j.chemphys.2009.07.003","article-title":"Role of the reacting free radicals on the antioxidant mechanism of curcumin","volume":"363","author":"Galano","year":"2009","journal-title":"Chem. Phys."},{"key":"ref_26","first-page":"699","article-title":"Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor","volume":"28","author":"Murakami","year":"2008","journal-title":"Anticancer Res."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1016\/S0891-5849(03)00325-3","article-title":"Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin","volume":"35","author":"Priyadarsini","year":"2003","journal-title":"Free Radic. Biol. Med."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1021\/ol047766e","article-title":"Successful application of TD-DFT in transient absorption spectra assignment","volume":"7","author":"Shen","year":"2005","journal-title":"Org. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2331","DOI":"10.1021\/jp7108303","article-title":"Spectroscopic and theoretical study of the electronic structure of curcumin and related fragment molecules","volume":"112","author":"Galasso","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_30","first-page":"2093","article-title":"Chemical and structural features influencing the biological activity of curcumin","volume":"19","author":"Priyadarsini","year":"2013","journal-title":"Curr. Pharm. Des."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jmgm.2017.10.022","article-title":"Metal chelating ability and antioxidant properties of Curcumin-metal complexes\u2014A DFT approach","volume":"79","author":"Mary","year":"2018","journal-title":"J. Mol. Graph. Model."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1186\/s42269-020-00391-z","article-title":"Molecular design of curcumin analogues with potent antioxidant properties and thermodynamic evaluation of their mechanism of free radical scavenge","volume":"44","author":"Alisi","year":"2020","journal-title":"Bull. Natl. Res. Cent."},{"key":"ref_33","first-page":"e13584","article-title":"Antioxidant properties of novel curcumin analogues: A combined experimental and computational study","volume":"45","author":"Angelova","year":"2021","journal-title":"J. Food Biochem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1007\/s00894-021-04778-1","article-title":"Radical scavenger competition of alizarin and curcumin: A mechanistic DFT study on antioxidant activity","volume":"27","author":"Sadatsharifi","year":"2021","journal-title":"J. Mol. Model."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5649","DOI":"10.1039\/D4RA07769E","article-title":"HOO radical scavenging activity of curcumin I and III in physiological conditions: A theoretical investigation on the influence of acid-base equilibrium and tautomerism","volume":"15","author":"Truong","year":"2025","journal-title":"RSC Adv."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"7551","DOI":"10.1080\/07391102.2022.2123043","article-title":"Synthesis, spectroscopic characterization, density functional theory study, antimicrobial and antioxidant activities of curcumin and alanine-curcumin Schiff base","volume":"41","author":"Layaida","year":"2023","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5769","DOI":"10.1080\/07391102.2021.1873190","article-title":"Immunomodulatory and anti-cytokine therapeutic potential of curcumin and its derivatives for treating COVID-19\u2014A computational modeling","volume":"40","author":"Noor","year":"2022","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_38","first-page":"1091","article-title":"Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition","volume":"60","year":"2024","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_39","first-page":"402","article-title":"Studies on curcumin and curcuminoids. VI. Kinetics of curcumin degradation in aqueous solution","volume":"180","author":"Karlsen","year":"1985","journal-title":"Z. Lebensm. Unters. Forsch."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1016\/S0020-1693(01)00687-9","article-title":"Curcuminoids as potential new iron-chelating agents: Spectroscopic, polarographic and potentiometric study on their Fe(III) complexing ability","volume":"328","author":"Borsari","year":"2002","journal-title":"Inorganica Chim. Acta"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1355","DOI":"10.1021\/jf0111965","article-title":"Study on the supramolecular interaction of curcumin and beta-cyclodextrin by spectrophotometry and its analytical application","volume":"50","author":"Tang","year":"2002","journal-title":"J. Agric. Food Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/B978-0-12-800173-8.00003-9","article-title":"Curcumin","volume":"39","author":"Lestari","year":"2014","journal-title":"Profiles Drug Subst. Excip. Relat. Methodol."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"8314","DOI":"10.1021\/acs.jpca.9b05380","article-title":"Assessment of pKa determination for monocarboxylic acids with an accurate theoretical composite method: G4CEP","volume":"123","author":"Custodio","year":"2019","journal-title":"J. Phys. Chem. A"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1021\/acs.jpca.0c08283","article-title":"On the accuracy of the direct method to calculate pKa from electronic structure calculations","volume":"125","author":"Dutra","year":"2021","journal-title":"J. Phys. Chem. A"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Walton-Raaby, M., Floen, T., Garc\u00eda-D\u00edez, G., and Mora-Diez, N. (2023). Calculating the aqueous pKa of phenols: Predictions for antioxidants and cannabinoids. Antioxidants, 12.","DOI":"10.3390\/antiox12071420"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1002\/jcc.10189","article-title":"Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model","volume":"24","author":"Cossi","year":"2003","journal-title":"J. Comput. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/S0166-1280(98)00553-3","article-title":"The IEF version of the PCM solvation method: An overview of a new method addressed to study molecular solutes at the QM ab initio level","volume":"464","author":"Tomasi","year":"1999","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1520","DOI":"10.1021\/jp810292n","article-title":"Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions","volume":"113","author":"Marenich","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"ref_49","unstructured":"Parr, R.G., and Yang, W. (1989). Density-Functional Theory of Atoms and Molecules, Oxford University Press."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density-functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_52","doi-asserted-by":"crossref","unstructured":"Molski, M. (2025). Computation of the pKa values of gallic acid and its anionic forms in aqueous solution: A self-similar transformation approach for accurate proton hydration free energy estimation. Molecules, 30.","DOI":"10.3390\/molecules30030742"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1007\/s10953-009-9483-3","article-title":"A Combined theoretical and experimental approach to the study of the structural and electronic properties of curcumin as a function of the solvent","volume":"39","author":"Benassi","year":"2010","journal-title":"J. Solut. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1525","DOI":"10.1021\/acs.jafc.6b04815","article-title":"Physical and chemical ctability of curcumin in aqueous solutions and emulsions: Impact of pH, temperature, and molecular environment","volume":"65","author":"Kharat","year":"2017","journal-title":"J. Agric. Food Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1016\/j.saa.2014.05.096","article-title":"The effect of the water on the Curcumin tautomerism: A quantitative approach","volume":"132","author":"Manolova","year":"2014","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"121287","DOI":"10.1016\/j.saa.2022.121287","article-title":"Keto-enol tautomerism of curcumin in the preparation of nanobiocomposites with fumed silica","volume":"277","author":"Kazakova","year":"2022","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"34022","DOI":"10.1021\/acsomega.3c04907","article-title":"First-Principles study of the dispersion effects in the structures and keto-enol tautomerization of curcumin","volume":"8","author":"Madinah","year":"2023","journal-title":"ACS Omega"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4989","DOI":"10.1021\/ct300778e","article-title":"A Density Functional with Spherical Atom Dispersion Terms","volume":"8","author":"Austin","year":"2012","journal-title":"J. Chem. Theory Comput."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"6615","DOI":"10.1039\/b810189b","article-title":"Long-range corrected hybrid density functionals with damped atom\u2013atom dispersion corrections","volume":"10","author":"Chai","year":"2008","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/j.theochem.2010.04.002","article-title":"Study of the solvent effect on the enthalpies of homolytic and heterolytic N\u2013H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine","volume":"952","author":"Klein","year":"2010","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"16635","DOI":"10.1021\/ja305668h","article-title":"Multiple-site concerted proton-electron transfer reactions of hydrogen-bonded phenols are nonadiabatic and well described by semiclassical Marcus theory","volume":"134","author":"Schrauben","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"560","DOI":"10.1021\/jacs.0c09106","article-title":"Proton-coupled electron transfer guidelines, fair and square","volume":"143","author":"Tyburski","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1383","DOI":"10.1021\/jacsau.2c00085","article-title":"Describing chemical reactivity with frontier molecular orbitals","volume":"2","author":"Yu","year":"2022","journal-title":"JACS Au"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/S0031-8914(34)90011-2","article-title":"\u00dcber die zuordnung von wellenfunktionen und eigenwerten zu den einzelnen elektronen eines atoms","volume":"1","author":"Koopmans","year":"1934","journal-title":"Physica"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1039\/C3MH00098B","article-title":"Mind the gap!","volume":"1","author":"Bredas","year":"2014","journal-title":"Mater. Horiz."},{"key":"ref_66","doi-asserted-by":"crossref","unstructured":"Pearson, R.G. (1997). Chemical Hardness\u2014Applications from Molecules to Solids, Wiley.","DOI":"10.1002\/3527606173"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"4700","DOI":"10.1021\/acs.jpca.0c01342","article-title":"On electronegativity, hardness, and reactivity descriptors: A new property-oriented basis set","volume":"124","author":"Zorrilla","year":"2020","journal-title":"J. Phys. Chem. A"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"1922","DOI":"10.1021\/ja983494x","article-title":"Electrophilicity index","volume":"121","author":"Parr","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_69","first-page":"1966","article-title":"Electrodonating and electroaccepting powers","volume":"111","author":"Cedillo","year":"2007","journal-title":"Phys. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4915","DOI":"10.1021\/jp8102436","article-title":"Donator acceptor map of psittacofulvins and anthocyanins: Are they good antioxidant substances?","volume":"113","author":"Martinez","year":"2009","journal-title":"J. Phys. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"827","DOI":"10.1002\/cjoc.20040220812","article-title":"Theoretical study on the antioxidant activity of curcumin","volume":"22","author":"Wang","year":"2004","journal-title":"Chin. J. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1069","DOI":"10.1002\/qua.20469","article-title":"DFT and experimental studies of the structure and vibrational spectra of curcumin","volume":"102","author":"Kolev","year":"2005","journal-title":"Int. J. Quantum Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"1021","DOI":"10.1007\/s10953-016-0481-y","article-title":"The Effect of solvent on tautomerism, acidity and radical stability of curcumin and its derivatives based on thermodynamic quantities","volume":"45","author":"Anjomshoa","year":"2016","journal-title":"J. Solut. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"2726","DOI":"10.1021\/acs.jnatprod.6b00726","article-title":"Solution conformations of curcumin in DMSO","volume":"79","author":"Slabber","year":"2016","journal-title":"J. Nat. Prod."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"15504","DOI":"10.1039\/C9CP00907H","article-title":"Interplay between conformational and solvent effects in UV\u2013visible absorption spectra: Curcumin tautomers as a case study","volume":"21","author":"Puglisi","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"5556","DOI":"10.1021\/acs.cgd.8b00859","article-title":"Capturing elusive polymorphs of curcumin: A structural characterization and computational study","volume":"18","author":"Matlinska","year":"2018","journal-title":"Cryst. Growth Des."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1591","DOI":"10.1021\/acs.jpca.1c08612","article-title":"Tautomers and rotamers of curcumin: A combined UV spectroscopy, high-performance liquid chromatography, ion mobility mass spectrometry, and electronic structure theory study","volume":"126","author":"Chatterjee","year":"2022","journal-title":"J. Phys. Chem. A"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1714","DOI":"10.1021\/acs.jcim.6b00310","article-title":"Empirically fitted parameters for calculating pKa values with small deviations from experiments using a simple computational strategy","volume":"56","author":"Galano","year":"2016","journal-title":"J. Chem. Inf. Model."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"11090","DOI":"10.1021\/jp508968z","article-title":"Revision of the thermodynamics of the proton in gas phase","volume":"118","author":"Fifen","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"e12806","DOI":"10.1016\/j.heliyon.2023.e12806","article-title":"Theoretical study on the radical scavenging activity of gallic acid","volume":"9","author":"Molski","year":"2023","journal-title":"Heliyon"},{"key":"ref_81","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Revision A.03, Gaussian, Inc."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"044115","DOI":"10.1063\/1.4974840","article-title":"Evaluation of DFT-D3 dispersion corrections for various structural benchmark sets","volume":"146","author":"Schwabe","year":"2017","journal-title":"J. Chem. Phys."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"3297","DOI":"10.1039\/b508541a","article-title":"Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy","volume":"7","author":"Weigend","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"e202400380","DOI":"10.1002\/asia.202400380","article-title":"Recent advances in the synthesis of diarylheptanoids","volume":"19","author":"Sudarshan","year":"2024","journal-title":"Chem. Asian J."},{"key":"ref_85","doi-asserted-by":"crossref","unstructured":"Molski, M. (2024). Theoretical Insight into Psittacofulvins and their derivatives. Molecules, 29.","DOI":"10.3390\/molecules29122760"},{"key":"ref_86","doi-asserted-by":"crossref","unstructured":"Molski, M. (2024). Enhancing Bioactivity through the transfer of the 2-(Hydroxymethoxy)vinyl moiety: Application in the modification of tyrosol and hinokitiol. Molecules, 29.","DOI":"10.3390\/molecules29143414"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/21\/10374\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,27]],"date-time":"2025-10-27T00:54:29Z","timestamp":1761526469000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/26\/21\/10374"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,10,24]]},"references-count":86,"journal-issue":{"issue":"21","published-online":{"date-parts":[[2025,11]]}},"alternative-id":["ijms262110374"],"URL":"https:\/\/doi.org\/10.3390\/ijms262110374","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,10,24]]}}}