Salicortin(1), a phenolic glycoside found in many species of Populus and Salix trees, has shown ecological significance as a natural insecticide and antifeedant to some small mammals, such as snowshoe hares. Thieme first proposed the structure of salicortin in 1964, and later studies performed by Pearl and Darling involving chemical decomposition and spectral techniques were consistent with Thieme's results. However, the remote stereocenter at C-9 of the aliphatic ring was not determined. A related compound containing a C-2' benzoate ester was isolated in 1966 and called tremualcin. Our research goal was to ascertain the absolute configuration at the unknown center of these compounds. Direct structural determination of salicortin was not possible due to the stereochemical complexities arising from the glucose units. By fragmenting the compound apart into several smaller components, the isolated aliphatic ring could then be converted to a Mosher ester. The carbonyl located on the aliphatic ring of salicortin was converted to an alcohol, forming salicortinol via reduction using both ZnBH₄ (giving a 1:1 mixture of diastereomers) and BH₃ (to give a single stereoisomer) in yields of 70%. Base-catalyzed and enzymatic hydrolyses, along with a variety of hydride reductions, were employed in an effort to isolate the aliphatic ring. Kinetic studies were performed on salicortinol using a Β-glucosidase at 21°C. Results showed that the deactivation rate of the enzyme was comparable to that of salicortin, which had previously been reported.