A novel synthesis of (.+-.)-cinnamodial

Burton, Lester P. J.; White, James D.

doi:10.1021/ja00401a057

Cited by 36 publications

(21 citation statements)

References 2 publications

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“…1 (k! =3.8 x lo6 M-' *s-'), than for any other phenols then known [4]. This was explained in stereoelectronic terms with reference to the dihedral angle, 8 (-17" for 1) [4] between the p-type lone pair orbital on 01 and a perpendicular to the aromatic plane, an angle which is equal to the dihedral angle between the O&Z bond and the aromatic plane [4].…”

Section: Introductionmentioning

confidence: 89%

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A new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay

et al. 1986

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Vitamin E owes its biological effects to its antioxidant activity. Kinetic and mechanistic studies on phenolic antioxidants in vitro have led us to design and synthesize all‐rac‐2,4,6,7‐tetramethyl‐2‐(4',8',12'‐trimethyltridecyl)‐5‐hydroxy‐3,4‐dihydrobenzofuran, 3. In the rat curative myopathy bioassay the acetate of this compound has 1.5–1.9 times the bioactivity of all‐rac‐α‐tocopherol acetate. This represents the first time that a rationally designed synthetic ‘vitamin’ has been found to have more activity in vivo than the corresponding natural vitamin.

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Section: Introductionmentioning

confidence: 89%

“…ROO' + ArOH% ROOH + ArO-(1) a-Tocopherol (a-T) is biologically the most active of the four tocopherols [l]. It is also the most active at trapping peroxyls in vitro [4]. Indeed, we found that the rate constant for ROO * trapping, kl, was higher for LY-T (kYwT=3.2x lo6 M-' 's-l) and related compounds, e.g.…”

Section: Introductionmentioning

confidence: 96%

A new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay

et al. 1986

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“…Over recent decades, much work has been done to clarify the basic principles that determine the rates of reaction (1) and to synthesize compounds that show k inh values higher than a-tocopherol, [2] the most effective lipid-soluble antioxidant present in nature. Actually, several of the synthetic Abstract: Sulfur-containing analogues of vitamin E (thiachromanols), either linked or not to a catechol moiety, were synthesized and their hydrogenatom donating ability evaluated.…”

Section: Introductionmentioning

confidence: 99%

Kinetic and Thermochemical Study of the Antioxidant Activity of Sulfur‐Containing Analogues of Vitamin E

Amorati¹,

Cavalli²,

Fumo³

et al. 2007

Chemistry A European J

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Sulfur-containing analogues of vitamin E (thiachromanols), either linked or not to a catechol moiety, were synthesized and their hydrogen-atom donating ability evaluated. The determination of the O--H bond dissociation enthalpy (BDE) of the alpha-tocopherol analogue 4 by the electron paramagnetic resonance (EPR) equilibration technique provided a value of 78.9 kcal mol(-1), that is, approximately 1.8 kcal mol(-1) higher than that of alpha-tocopherol. The kinetic rate constants for the reaction with peroxyl radicals (kinh), measured by inhibited autoxidation studies, showed that thiachromanols react 2.5 times slower than the corresponding tocopherols, in agreement with the higher BDE value. This behavior was explained, on the basis of crystallographic analyses and DFT calculations, in terms of a change in the molecular geometry caused by insertion of a sulfur atom into the framework of vitamin E. This behavior implies a greater deviation of the condensed ring from coplanarity with the aromatic ring, thus giving rise to a decrease in the conjugative stabilization of the phenoxyl radical and consequently to an increase in the O--H bond strength. Although less reactive than tocopherols, thiachromanols may, however, act as bimodal antioxidants as a result of the hydroperoxide decomposing ability of the sulfur atom.

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“…1). K-TOH has a higher antioxidant activity in vitro [11]. Levels of K-TOH in vivo (in humans) are several fold higher than those of Q-TOH [12].…”

Section: Introductionmentioning

confidence: 99%

Interaction of peroxynitrite with carotenoids and tocopherols within low density lipoprotein

et al. 1998

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Peroxynitrite is a powerful oxidising and nitrating agent generated in vivo by the combination of nitric oxide and superoxide. Previous studies have shown that on exposure to peroxynitrite, low density lipoprotein (LDL) is modified resulting in both a time-and concentration-dependent change to lipid and protein components. The present investigation highlights the reaction between carotenoids and tocopherols, present within the lipophilic phase of LDL, and peroxynitrite at varying concentrations. It was observed that the carotenoids were consumed by a significantly greater proportion than that of the tocopherols with lycopene (87.2 þ 11%) being more reactive than L L-carotene (68.2 þ 5.8%) when exposed to peroxynitrite (50 W WM) for 1 min. Among the tocopherols, K K-tocopherol (54.9 þ 20.2%) was more extensively depleted than Q Q-tocopherol (14.7 þ 1.09%) at peroxynitrite concentration of 500 W WM. It was also observed that peroxynitrite, unlike copper ions, does not lead to significant peroxidation of LDL as determined by the formation of conjugated dienes and thiobarbituric acid-reactive substances.z 1998 Federation of European Biochemical Societies.

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A novel synthesis of (.+-.)-cinnamodial

Cited by 36 publications

References 2 publications

A new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay

A new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay

Kinetic and Thermochemical Study of the Antioxidant Activity of Sulfur‐Containing Analogues of Vitamin E

Interaction of peroxynitrite with carotenoids and tocopherols within low density lipoprotein

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