Reaction of 3-Dehydroshikimic Acid with Molecular Oxygen and Hydrogen Peroxide: Products, Mechanism, and Associated Antioxidant Activity
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- 作者：Jack E. Richman ; Yu-Chen Chang ; Spiros Kambourakis ; K. M. Draths ; Erick Almy ; Kristi D. Snell ; Gale M. Strasburg ; and J. W. Frost
- 刊名：Journal of the American Chemical Society
- 出版年：1996
- 出版时间：November 20, 1996
- 年：1996
- 卷：118
- 期：46
- 页码：11587 - 11591
- 全文大小：169K
- 年卷期：v.118,no.46(November 20, 1996)
- ISSN：1520-5126
文摘
In the presence of molecular oxygen or hydrogen peroxide,inorganic phosphate catalyzes the conversionof 3-dehydroshikimic acid (DHS) into gallic acid. Other productsformed in the reaction of DHS with oxygeninclude protocatechuic acid, tricarballylic acid, and pyrogallol.With hydrogen peroxide as oxidant, pyrogallolformation is not observed, and smaller amounts of tricarballylic acidare produced. Evidence favoring a mechanisminvolving phosphate-catalyzed tautomerization of DHS to a reactiveenediol intermediate follows from the successfulisolation of dihydrogallic acid when oxidant is excluded fromphosphate-buffered solutions of DHS. The reductone-like solution chemistry of DHS and the radical quenching reactivity ofthe phenolics formed from DHS prompted anappraisal of DHS antioxidant activity. Based on two differentanalyses, DHS was discovered to possess significantantioxidant activity relative to 
es/gifchars/alpha.gif" BORDER=0>-tocopherol, gallic acid, propylgallate, and tert-butylhydroquinone.