A Novel Oxidative Dimer from Protocatechuic Esters: Contribution to the Total Radical Scavenging Ability of Protocatechuic Esters | Zendy

Shizuka Saito | Zendy; Jun Kawabata | Zendy

Open Access

A Novel Oxidative Dimer from Protocatechuic Esters: Contribution to the Total Radical Scavenging Ability of Protocatechuic Esters

Author(s) -

Shizuka Saito,

Jun Kawabata

Publication year - 2008

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1271/bbb.80130

Subject(s) - chemistry , protocatechuic acid , dimer , catechol , scavenging , methanol , radical ion , alcohol , dpph , nucleophile , solvent , octane , organic chemistry , ferric , antioxidant , medicinal chemistry , photochemistry , catalysis , ion

A novel oxidative dimer was isolated as a major product from a reaction mixture of methyl protocatechuate and DPPH radical in methanol. Its unusual benzobicyclo[3.2.1]octane structure was elucidated by extensive spectral analysis. This result suggests that the regeneration of catechol structures by the nucleophilic addition of an alcohol molecule on o-quinones and subsequent dimerization is one of the key reactions in the high radical-scavenging activity of protocatechuic esters in an alcoholic solvent.

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