Romain Guitard, Véronique Nardello-Rataj and Jean-Marie Aubry. Table S1. Bond Dissociation Enthalpies BDEs (O-H). BDE O-H (kcal mol 1 )

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1 S1 of S13 Supplementary Materials: Theoretical and Kinetic Tools for Selecting Effective Antioxidants: Application to the Protection of Omega-3 Oils with Natural and Synthetic Phenols Romain Guitard, Véronique Nardello-Rataj and Jean-Marie Aubry Table S1. Bond Dissociation Enthalpies BDEs (O-H). Synthetic antioxidants Tert-butyl-pyrogallol 2 Pyrogallol 3 Hydroxyquinol 3, , Propyl gallate 3, BHA Tert-butyl-catechol BHT TBHQ o-tert-butyl-p-cresol Phloroglucinol 1,3,5 83.0

2 S2 of S13 Tocopherols 11 α-tocopherol β-tocopherol γ-tocopherol δ-tocopherol Derivatives of hydroxybenzoic acids Gallic acid 3, Protocatechuic acid Syringic acid Ellagic acid Gentisic acid Vanillic acid PHBA Salicylic acid

3 S3 of S13 23 Rosmarinic acid Hydroxycinnamic acid derivatives Caffeic acid Chlorogenic acid Sinapic acid Ferulic acid o-coumaric acid p-coumaric acid m-coumaric acid

4 S4 of S13 31 Gossypetin 32 Myricetin 33 Azaleatin Flavonols Quercetin 35 Fisetin Laricitrin 37 Syringetin Rhamnazin Kaempferide

5 S5 of S Isorhamnetin Morin 42 Kaempferol 43 Galangin Flavones 44 Luteolin HO 7 O OH 3' OH 4' Apigenin 5 OH O Taxifolin 47 Aromadedrin Flavanonols

6 S6 of S13 Flavanones 48 Eriodictyol HO O 49 Homoeriodictyol 7 5 OH O OH 3' OH 4' Hesperetin Naringenin Glycitein 53 Genistein Isoflavones HO O 7 O O 4' OH Daidzein

7 S7 of S13 55 Epigallocatechin gallate 56 Gallocatechin 57 Catechin Catechins Piceatannol Stilbenes Resveratrol Eugenol derivatives 60 Isoeugenol Eugenol Hydroxytyrosol Antioxidants found in olive oil Catechol 1, Tyrosol

8 S8 of S13 Lignans 65 Sesamol Methylesculetin 67 Aesculetin Coumarins Nordalbergin Carnosol Antioxidants found in Rosemary extract Carnosic acid Table S2. Kinetic rate constants of hydrogen transfer from phenolic antioxidants to the DPPH radical in toluene at 20 C. Phenols Methods 10 4 [DPPH ] (M) 10 3 [ArOH]0 (M) 10 3 kapp k (M 1 s 1 ) SOK SOK SOK SOK FOK SOK

9 S9 of S13 Table S2. Cont. Phenols Methods 10 4 [DPPH ] (M) 10 3 [ArOH]0 (M) 10 3 kapp k (M 1 s 1 ) FOK SOK SOK SOK FOK SOK SOK SOK FOK SOK SOK SOK SOK SOK SOK

10 S10 of S13 Table S3. Determination of the stoichiometric numbers (σexp) of the hydrogen transfer from phenols to the DPPH radical in toluene at 20 C at 515 nm, [DPPH ] = mol L 1. Phenols 10 5 [ArOH]0 (M) A0 Af σexp * * * * * * * * * * * *: ethyl acetate used as solvent; nd: not determined Table S4. Induction periods (IP) and oxidation rates (Rox) for the inhibition of FAMEs linseed oil oxidation by phenolic antioxidants during the Rapidoxy test. Phenols Induction Period IP (min) 230 IP Average (min) Std. dev. IP (min) Oxidation rate Rox (mm min 1 ) Rox Average (mm min 1 ) Std. dev. Rox (mm min 1 )

11 S11 of S13 Phenols Induction Period IP (min) 43 IP Average (min) Table S4. Cont. Std. dev. IP (min) Oxidation rate Rox (mm min 1 ) Rox Average (mm min 1 ) Std. dev. Rox (mm min 1 )

S12 of S13 Phenols Induction Period IP (min) 169 IP Average (min) Table S4. Cont. Std. dev. IP (min) Oxidation rate Rox (mm min 1 ) 0.29 Rox Average (mm min 1 ) Std. dev. Rox (mm min 1 ) 62 175 172 3 0.

12 S12 of S13 Phenols Induction Period IP (min) 169 IP Average (min) Table S4. Cont. Std. dev. IP (min) Oxidation rate Rox (mm min 1 ) 0.29 Rox Average (mm min 1 ) Std. dev. Rox (mm min 1 ) ml of FAMEs linseed oil, [phenols]0 = 0.5 mm, T = 90 C, P = 450 kpa, Std. dev. = Standard deviation Lag time = 2s 1 A at 517nm Time (s) Figure S1. Equipment for UV-visible analysis and evolution of the absorbance of DPPH radical at 515 nm (0.12 mm) without phenol in toluene at 20 C (visualization of the lag time).

13 S13 of S13 BDE Guitard et al. (kcal mol -1 ) y = 1.06x R² = BDE Leopoldini et al. (kcal mol -1 ) Figure S2. Correlation of BDEs obtained by Guitard et al. and Leopoldini et al. [22]. 90 BDE Guitard et al. (kcal mol -1 ) y = 1.01x R² = BDE Li et al. (kcal mol -1 ) Figure S3. Correlation of BDEs obtained by Guitard et al. and Li et al. [23]. 85 BDE Guitard et al. (kcal mol -1 ) y = 0.99x R² = BDE Pérez-Gonzalez et al. (kcal mol -1 ) Figure S4. Correlation of BDEs obtained by Guitard et al. and Pérez-Gonzalez et al. [20].

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