The Isolation and Identification of Wynephrine in the Leaves and Fruit of Citrus*

During a study of the relationship between trace element deficiencies and the free amino acids in citrus, an unknown basic nitrogen compound was detected in leaf extracts. In most samples there was more of the unknown constituent than of any other basic nitrogen compound. However, it was not present in leaf samples from trees with manganese deficiency. A comparison of its paper chromatographic RF values with those of many known materials suggested that it was a compound not commonly found in plants. After extraction and isolation, it was identified by degradation studies and infrared analyses as l-p-hydroxy-cr(methylaminomethyl)benzyl alcohol, (synephrine, Sympatol),