Hydrolysis of Indole-3-Acetic Acid Esters Exposed to Mild Alkaline Conditions

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Abstract
Ester conjugates of indole-3-acetic acid are hydrolyzed easily in basic solutions; however, quantitative data have not been available on the relationship between pH and rate of hydrolysis of the known ester conjugates. The use of basic conditions during extraction or purification of IAA by several laboratories suggested that a more systematic analysis of this process was needed. In this report we present data indicating: (a) that measurable hydrolysis of IAA-glucose (from standard solutions) and IAA-esters (from maize kernel extracts) occurs with only a few hours of treatment at pH 9 or above; (b) that the lability of some ester conjugates is even greater than that of IAA-glucose; and (c) that ester hydrolysis of standard compounds, IAA-glucose and IAA-p-nitrophenol, occurs in the ''three phase extraction system'' proposed by Liu and Tillberg ([1983] Physiol Plant 57: 441-447). These data indicate that the potential for problems with inadvertent hydrolysis of ester conjugates of IAA exists even at moderate pH values and in the multiphase system where exposure to basic conditions was thought to be limited.