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Volumn 48, Issue 1, 2009, Pages 157-160

Garlic: Source of the ultimate antioxidants - Sulfenic acids

Author keywords

Allicin; Antioxidants; Garlic; Lipid peroxidation; Peroxyl radicals; Proton coupled electron transfer

Indexed keywords

ACIDS; CHEMICAL PROPERTIES; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; METABOLITES; OXIDATION; PROTON TRANSFER; PROTONS; SULFUR;

EID: 58249101189     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804560     Document Type: Article
Times cited : (108)

References (30)
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    • See, for example, references 11-20 in
    • See, for example, references 11-20 in Ref. [5b].
    • , vol.5 b
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    • Such a large difference in the rate constants of reactions of radical-trapping antioxidants with secondary and tertiary peroxyl radicals is unprecedented. Also, the inhibition rate constants were based on the assumption that one molecule of allicin reacts with one chain-carrying peroxyl radical in the autoxidation of each substrate stoichiometric factor: n, 1, an assumption that is invalid on the basis of the actual inhibition periods observed,[5b] which correspond to stoichiometric factors of approximately 0.3
    • [5b] which correspond to stoichiometric factors of approximately 0.3.
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    • Appropriately substituted carbon-centered radicals, such as that derived from HP-136, are an exception; see: J. C. Scaiano, A. Martin, G. P. A. Yap, K. U. Ingold, Org. Lett. 2000, 2, 899.
    • Appropriately substituted carbon-centered radicals, such as that derived from HP-136, are an exception; see: J. C. Scaiano, A. Martin, G. P. A. Yap, K. U. Ingold, Org. Lett. 2000, 2, 899.
  • 15
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    • For other highly reactive radical-trapping antioxidants, see: M. Wijtmans, D. A. Pratt, L. Valgimigli, G. A. DiLabio, G. F. Pedulli, N. A. Porter, Angew. Chem. 2003, 115, 4506; Angew. Chem. Int. Ed. 2003, 42, 4370;
    • For other highly reactive radical-trapping antioxidants, see: M. Wijtmans, D. A. Pratt, L. Valgimigli, G. A. DiLabio, G. F. Pedulli, N. A. Porter, Angew. Chem. 2003, 115, 4506; Angew. Chem. Int. Ed. 2003, 42, 4370;
  • 18
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    • [1] In our inhibited autoxidation reactions, the addition of ethyl propiolate to the reaction mixture did not prevent inhibition, presumably since the reaction of 2-propenesulfenic acid with peroxyl radicals is much faster than its addition to ethyl propiolate.
    • [1] In our inhibited autoxidation reactions, the addition of ethyl propiolate to the reaction mixture did not prevent inhibition, presumably since the reaction of 2-propenesulfenic acid with peroxyl radicals is much faster than its addition to ethyl propiolate.
  • 19
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    • [10] that sulfenic acids undergo other reactions, such as reaction with oxygen, during autoxidation processes.
    • [10] that sulfenic acids undergo other reactions, such as reaction with oxygen, during autoxidation processes.
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    • [16]
    • [16]
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    • -1).
    • -1).
  • 29
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    • Sulfinic and sulfonic acids, the oxidation products of sulfenic acids, would not be expected to be good peroxyl-radical scavengers, since the lone pair of electrons on the sulfur atom would either be too low in energy (former) or unavailable (latter) for the five-center PCET reaction
    • Sulfinic and sulfonic acids, the oxidation products of sulfenic acids, would not be expected to be good peroxyl-radical scavengers, since the lone pair of electrons on the sulfur atom would either be too low in energy (former) or unavailable (latter) for the five-center PCET reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.