Abstract: Fifteen condensates of chiral amines and racemic gossypol were prepared.Their ¹HNMR spectra indicated that all the amine condensates tested had the same keto-enamine structures and shitts of protons on C₁₁,C₁₁ of various condensates were analyzed for their structural relationship. The Rf and △Rf values (difference between (+)and (-)gossypol condensates)on TLC of these derivatives and stability of eight condensates of (-)gossypol were examined. All these properties Were discussed in light of the configuration of gossypol. These studies not only provided rational basis of selecting resoioving agent,but also gave indications of their relative adsorbability and stereochemistry of the condensates which might be useful in postulating theirs in vivo behaviors and designing derivatives with better pharmacological actions.