Quinone hemiacetal formation from protocatechuic acid during the DPPH radical scavenging reaction

Shizuka Saito; Yasuko Okamoto; Jun Kawabata; Takanori Kasai

doi:10.1271/bbb.67.1578

Quinone hemiacetal formation from protocatechuic acid during the DPPH radical scavenging reaction

Biosci Biotechnol Biochem. 2003 Jul;67(7):1578-9. doi: 10.1271/bbb.67.1578.

Authors

Shizuka Saito¹, Yasuko Okamoto, Jun Kawabata, Takanori Kasai

Affiliation

¹ Laboratory of Food Biochemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Sapporo, Japan.

PMID: 12913304
DOI: 10.1271/bbb.67.1578

Abstract

Protocatechuic acid was rapidly converted to protocatechuquinone 3-methyl hemiacetal and protocatechuquinone during the reaction with DPPH radical in methanol. The structure of the acetal was determined by comparing the NMR data with those of an authentic compound prepared by (diacetoxy)iodobenzene oxidation of protocatechuic acid.

MeSH terms

Biphenyl Compounds
Free Radical Scavengers / chemistry*
Free Radicals / chemistry*
Hydroxybenzoates / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Oxidation-Reduction
Picrates / chemistry*
Quinones / chemical synthesis*

Substances

Biphenyl Compounds
Free Radical Scavengers
Free Radicals
Hydroxybenzoates
Picrates
Quinones
protocatechuic acid
1,1-diphenyl-2-picrylhydrazyl