Indol-3-ylacetic acid, metabolic degradation

The mechanism of metabolic degradation of indol-3-ylacetic acid (39) is a matter of debate. A possible route demonstrated in vitro includes oxidative decarboxylation to skatolyl hydroperoxide (40), catalyzed by horseradish peroxidase isoenzyme C (HRP-C), followed by rearrangement to 3-(hydroxymethyl)oxindole (41), as shown in equation 12 . 

The MS of compound 40, a putative intermediate of the metabolic degradation of indol-3-ylacetic acid (39), shows the molecular peak at m e 163 and the parent negative peak at 162. This and other spectral and chemical evidence pointed to the compound being a hydroperoxide . 

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See also in sourсe #XX -- [ , ]

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