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.
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