Nordihydroguaiaretic acid autoxidation produces a schisandrin-like dibenzocyclooctadiene lignan.
The lignan meso-nordihydroguaiaretic acid is known to undergo spontaneous oxidation in alkaline solution. In the presence of the trapping agent glutathione, the major oxidation products are consistent with the formation of a meso-nordihydroguaiaretic acid ortho-quinone. In the absence of a trapping agent however, the major oxidation product of meso-nordihydroguaiaretic acid in aqueous solution is a unique, stable schisandrin-like dibenzocyclooctadiene lignan that may be responsible for some of the biological effects of nordihydroguaiaretic acid.
Billinsky
Jennifer L
JL
Graduate Toxicology Program, University of Saskatchewan, Saskatoon, SK Canada.
Krol
Ed S
ES
D034242:Cyclooctanes / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry*; D009637:Masoprocol / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D034242:Cyclooctanes; D017705:Lignans; D011083:Polycyclic Compounds; C510994:dibenzocyclooctadiene lignan; D009637:Masoprocol; C011105:schizandrin