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. Author manuscript; available in PMC: 2008 Jul 1.
Published in final edited form as: Free Radic Biol Med. 2007 Mar 31;43(1):4–15. doi: 10.1016/j.freeradbiomed.2007.03.024

Table.

Chemical Assessments of the Antioxidant Abilities of Tocopherols in Organic Solution and Aqueous Suspension of Phospholipids

Rates Antioxidant Efficiencies Fetal Resorption Assay

ks ·10-3M-1 s-1 ks ·10-5 M-1 s-1 k5 ·10-4 M-1 s-1 K1 ·10-4 M-1 s-1 k1 ·10-4 M-1 s-1
[52] [55] [51] [50] [50] [53] [53] [54] [56]
EtOH Triton Micelle IAS LKEPR 0.10 M HDTBr 0.10 M SDS 0.5 M SDS % of all rac α-tocopheryl acetate
Footnotes: {a} {b} {c} {d} {d} {e} {e} {f} {g}
Conjugated dienes Conjugated dienes O2uptake
α-Tocopherol 5.12 5.12 235 ± 50 320 260 1770 ± 90 1830 ± 50 1000 80
β-Tocopherol 2.24 1.05 166 ± 33 130 970 ± 140 950 ± 30 590 45
γ-Tocopherol 2.42 1.00 159 ± 42 140 70 1020 ± 40 980 ± 60 590 13
δ-Tocopherol 1 0.149 65 ± 13 44 33 530 ± 30 570 ± 50 240 <0.4
Tocol 0.56 0.0353
PMC 214 ± 81 380 2850 ± 100 2880 ± 120 4050
Trolox 110 8300 ± 360 1320 ± 90 2970

PMC = 2,3,5,7,8-pentamethylchromanol, Tocol = 2-methyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol, Trolox = 6-Hydroxy-2,5,7,8- tetramethylchroman-2-carboxylic acid

{a}

ks is the second-order rate constant (in ethanol) for the H-atom abstraction of the various chromanols by the stable phenoxy radical of 3,5-di-tert-butyl-4’-methoxybiphenyl-4-ol at 25°C.

{b}

ks is the second-order rate constant (in 5% Triton X-100 micelles) for the H-atom abstraction of the various chromanols by the stable phenoxy radical of 3,5-di-tert-butyl-4’-methoxybiphenyl-4-ol at 25°C.

{c}

k5 is the second order rate constant for the H-atom abstraction of the various chromanols with peroxyradicals produced by the 2,2′-azo-bis(isobutyronitrile) (AIBN) initiated oxidation of styrene in chlorobenzene solution at 30°C

{d}

k1 is the second order rate constant for the H-atom abstraction of the various chromanols with peroxyradicals produced by AIBN initiated oxidation of styrene in chlorobenzene solution at 30°C; the so-called inhibited autoxidation of styrene (IAS) method essentially similar to that used in [51]. The laser kinetic electron paramagnetic resonance (LKEPR) method uses a laser pulse to decompose di-tert-butyl ketone in the presence of oxygen to quickly produce peroxyl radicals whose decay rate due to H-atom abstraction of the chromanols could be monitored by EPR.

{e and f}

Antioxidant Efficiencies (AE) are defined as kinh/kp where kinh is the second order rate constant for the reaction of peroxyl radicals from linoleic acid with the chromanols and kp is the second order propagation rate constant for the autoxidation of linoleic acid. Consequently, the AE values are without units. Linoleic acid was provided in hexadecyltrimethylammonium bromide (HDTBr) or sodium dodecylsulfate (SDS) supported micelles in the presence of the radical initiator 2,2′-azobis(2- amidinopropane) (ABAP) at pH 7.4. Rates of reactions were monitored by following conjugated diene formation at 234 nm [53] or O2-uptake [54].

{g}

Biological activities of orally provided chromanols are presented relative to all-rac-α-tocopheryl acetate (100%).