Theoretical investigation of stereochemistry and solvent influence on antioxidant activity of ferulic acid

Graf, 1992, Antioxidant potential of ferulic acid, Free Radic. Biol. Med., 13, 435, 10.1016/0891-5849(92)90184-I

Nabi, 2012, Ferulic and coumaric acids: application to release oxidative stress of DNA and methyl linoleate, J. Food Biochem., 36, 38, 10.1111/j.1745-4514.2010.00501.x

Niwa, 2001, Antioxidative properties of phenolic antioxidants isolated from corn steep liquor, J. Agric. Food Chem., 49, 177, 10.1021/jf0007885

Ogiwara, 2002, Radical scavenging activity and cytotoxicity of ferulic acid, Anticancer Res., 22, 2711

Rice-Evans, 1996, Structure-antioxidant activity relationships of flavonoids and phenolic acids, Free. Radic. Biol. Med., 20, 933, 10.1016/0891-5849(95)02227-9

Xiaokun, 2004, Purification and characterization of a feruloyl esterase from the intestinal bacterium Lactobacillus acidophilus, Appl. Environ. Microbiol., 70, 2367, 10.1128/AEM.70.4.2367-2372.2004

Takagi, 2005, Acute, subchronic and chronic toxicity studies of a synthetic antioxidant, 2,2′-isobutylidenebis(4,6-dimethylphenol) in rats, J. Toxicol. Sci., 30, 275, 10.2131/jts.30.275

Takagi, 1996, Chronic oral toxicity of a synthetic antioxidant, 2,2′-methylenebis(4-ethyl-6-tert-butylphenol), in rats, J. Appl. Toxicol., 16, 15, 10.1002/(SICI)1099-1263(199601)16:1<15::AID-JAT288>3.0.CO;2-N

Takagi, 1994, Acute, subchronic and chronic toxicity studies of a synthetic antioxidant, 2,2′-methylenebis(4-methyl-6-tert-butylphenol) in rats, J. Toxicol. Sci., 19, 77, 10.2131/jts.19.2_77

Takagi, 1993, Toxicity studies of a synthetic antioxidant, 2,2′-methylenebis (4-ethyl-6-tert-butylphenol) in rats. 2. Uncoupling effect on oxidative phosphorylation of liver mitochondria, J. Toxicol. Sci., 18, 49, 10.2131/jts.18.49

Takagi, 1992, Toxicity studies of a synthetic antioxidant, 2,2‘-methylenebis (4-ethyl-6-tert-butylphenol) in rats. 1. Acute and subchronic toxicity, J. Toxicol., Sci., 17, 135, 10.2131/jts.17.135

Saija, 1999, Ferulic and caffeic acids as potential protective agents against photooxidative skin damage, Sci. Food Agric., 79, 476, 10.1002/(SICI)1097-0010(19990301)79:3<476::AID-JSFA270>3.0.CO;2-L

Leopoldini, 2011, The molecular basis of working mechanism of natural polyphenolic antioxidants, Food Chem., 125, 288, 10.1016/j.foodchem.2010.08.012

Foti, 2004, Electron – transfer reaction of cinnamic acids and their methyl esters with the DPPH.radical in alcoholic solutions, J. Org. Chem., 69, 2309, 10.1021/jo035758q

Litwinienko, 2004, Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer, J. Org. Chem., 69, 5888, 10.1021/jo049254j

Musialik, 2005, Scavenging of dpph. radicals by vitamin E is accelerated by its partial ionization: the role of sequential proton loss electron transfer, Organic Lett., 7, 4951, 10.1021/ol051962j

Nakanishi, 2005, Electron – transfer mechanism in radical scavenging reactions by vitamin E model in a protic medium, Org. Biomol. Chem., 3, 626, 10.1039/b416572a

Litwinienko, 2007, Solvent effects on the rates and mechanisms of reaction of phenols with free radicals, Acc. Chem. Res., 40, 222, 10.1021/ar0682029

Szeląg, 2012, Quantum – chemical investigation of the structure and the antioxidant properties of α-lipoic acid and its metabolites, J. Mol. Model., 18, 2907, 10.1007/s00894-011-1306-y

Leopoldini, 2006, Gas and liquid phase acidity of natural antioxidants, J. Agric. Food Chem., 54, 3078, 10.1021/jf053180a

Mikulski, 2010, Quantum-chemical study on the antioxidation mechanisms of trans-resveratrol reactions with free radicals in the gas phase, water and ethanol environment, J. Mol. Struct.: TEOCHEM, 951, 37, 10.1016/j.theochem.2010.04.005

Klein, 2009, DFT/B3LYP Study of the O–H bond dissociation enthalpies and proton affinities of para- and meta-substituted phenols in water and benzene, Acta Chim. Slovaca, 2, 37

Rimarcik, 2010, Study of the solvent effect on the enthalpies of homolytic and heterolytic N–H bond cleavage in p-phenylenediamine and tetracyano-p-phenylenediamine, J. Mol. Struct.: TEOCHEM, 952, 25, 10.1016/j.theochem.2010.04.002

A. Urbaniak, M. Molski, M. Szeląg, Quantum-chemical calculations of the antioxidant properties of trans-p-coumaric acid and trans-sinapinic acid, CMST, vol. 18, 2012.

Martins, 2004, Toward the prediction of the activity of antioxidants: experimental and theoretical study of the gas-phase acidities of flavonoids, J. Am. Soc. Mass Spec., 15, 848, 10.1016/j.jasms.2004.02.007

Wright, 2001, Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants, J. Am. Chem. Soc., 123, 1173, 10.1021/ja002455u

Vafiadis, 2005, A DFT study on the deprotonation antioxidant mechanistic step of ortho-substituted phenolic cation radicals, Chem. Phys., 316, 195, 10.1016/j.chemphys.2005.05.015

Klein, 2007, DFT/B3LYP study of the substituent effect on the reaction enthalpies of the individual steps of sequential proton loss electron transfer mechanism of phenols antioxidant action: correlation with phenolic C–O bond length, J. Mol. Struct. THEOCHEM, 805, 153, 10.1016/j.theochem.2006.11.002

Klein, 2006, DFT/B3LYP Study of the substituent effect on the reaction enthalpies of the individual steps of single electron transfer-proton transfer and sequential proton loss electron transfer mechanisms of phenols antioxidant action, J. Phys. Chem. A, 110, 12312, 10.1021/jp063468i

Frisch, 2003

Hohenberg, 1964, Inhomogeneous electron gas, Phys. Rev. B, 136, B864, 10.1103/PhysRev.136.B864

Kohn, 1965, Self – consistent equations including exchange and correlation effects, Phys. Rev. A, 140, 1133, 10.1103/PhysRev.140.A1133

Lee, 1988, Development of the Cole – Salvetti correlation energy formula into a functional of the electron density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785

Cossi, 2003, Energies, structures, and electronic properties of molecules in solutions with the C-PCM solvation model, J. Comp. Chem., 24, 669, 10.1002/jcc.10189

Bartmess, 1994, Thermodynamics of the electron and the proton, J. Phys. Chem., 98, 6420, 10.1021/j100076a029

Atkins, 1998

Parker, 1992, Homolytic bond (H–A) dissociation free energies in solution – applications of the standard potential of the (H+/H) couple, J. Am. Chem. Soc., 114, 7458, 10.1021/ja00045a018

Bizarro, 1999, Substituent effects on the O–H bond dissociation enthalpies in phenolic compounds: agreements and controversies, Pure Appl. Chem., 71, 1249, 10.1046/j.1365-3075.1999.00279.x

Nethaji, 1988, Structure of 3-(4-Hydroxy-3-methoxyphenyl)-2-propenoic acid (Ferulic Acid), Acta Cryst., 44, 275

Calheiros, 2009, Conformational behavior of biologically active ferulic acid derivatives, J. Mol. Struct. THEOCHEM, 913, 146, 10.1016/j.theochem.2009.07.032

Sebastian, 2009, Molecular structure, spectroscopic studies and first-order molecular hyperpolarizabilities of ferulic acid by density functional study, Spectrochem. Acta, 74, 312, 10.1016/j.saa.2009.06.011

Bakalbassis, 2001, Ab initio and density functional theory studies for the explanation of the antioxidant activity of certain phenolic acids, Lipids, 36, 181, 10.1007/s11745-001-0705-9

Lii, 2002, Molecular mechanics (MM4) studies of carboxylic acids, esters, and lactones, J. Phys. Chem. A, 106, 8667, 10.1021/jp0142029

Mulder, 1988, O–H bond dissociation energies in para-substituted phenols, J. Am. Chem. Soc., 110, 4090, 10.1021/ja00220a088

Colussi, 1977, Very low-pressure pyrolysis of phenyl ethyl ether, phenyl allyl ether, and benzyl methyl-ether and enthalpy of formation of phenoxy radical, Inr. J. Chem. Kinet., 9, 161, 10.1002/kin.550090202

DeFrees, 1980, Heats of formation of gaseous free-radicals via ion-cyclotron double-resonance spectroscopy, J. Am. Chem. Soc., 102, 3334, 10.1021/ja00530a005

Walker, 1990, Single-pulse shock-tube studies on the thermal-decomposition of normal-butyl phenyl ether, normal-pentylbenzene, and phenetole and the heat of formation of phenoxy and benzyl radicals, J. Phys. Chem., 94, 3324, 10.1021/j100371a023

Arends, 1993, Kinetic study of the thermolysis of anisole in a hydrogen atmosphere, J. Phys. Chem., 97, 7914, 10.1021/j100132a020

Lind, 1990, The one-electron reduction potential of 4-substituted phenoxyl radicals in water, J. Am. Chem. Soc., 112, 479, 10.1021/ja00158a002

Bordwell, 1988, Homolytic bond dissociation energies in solution from equilibrium acidity and electrochemical data, J. Am. Chem. Soc., 110, 1229, 10.1021/ja00212a035

Nenadis, 2003, Structure_antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups, J. Agr. Food. Chem., 51, 1874, 10.1021/jf0261452

Klein, 2006, Study of gas-phase O–H bond dissociation enthalpies and ionization potentials of substituted phenols – applicability of ab initio and DFT/B3LYP methods, Chem. Phys., 330, 515, 10.1016/j.chemphys.2006.09.026