Simmondsin, an unusual 2-cyanomethylenecyclohexyl glucoside from Simmondsia californica

Abstract
Simmondsin, a monoglucoside extracted from seeds of the jojoba plant (Simmondsia californica), has been shown to be 2-(cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl β-D-glucoside (1). Analysis of the n.m.r. spectra of this compound and its penta-acetate permits assignment of the stereochemistry as well as establishing the point of attachment of the glucose.

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