Synthesis and Structure-Activity Relationships of Phaffiaol and Related Antioxidants

概要

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Total synthesis of a novel long chain alkyl phenol, phaffiaol (1), a potent antioxidant isolated from Phaffia rhodozyma, was achieved via three reaction steps starting from 3,5-dibromosalicylaldehyde (2). We also prepared several types of long chain alkyl phenol having different aromatic rings or different carbon length, and evaluated their antioxidative activity using the rabbit erythrocyte membrane ghost system. Amongst these compounds, the novel methoxy phenol derivatives (6c, d, 7) having a heptadecyl moiety at the ortho-position to the hydroxy group, were approximately 2 times more active than α-tocopherol. In addition, 4-methoxy-2-pentadexylphenol (10h), which has a 15-carbon length in the side chain moiety, showed the maximum activity.
公益社団法人日本薬学会の論文
1998-11-15