Spontaneous conversion of gossypol to anhydrogossypol

An alkali-fast pigment is produced at room temperature when gossypol is dissolved in ethyl acetate. This pigment has been isolated from ethyl acetate as an orange crystalline material and identified as anhydrogossypol. The identity was established by identity of the infrared spectra with that of authentic anhydrogossypol; by elementary composition; by mixture-melting point behavior with authentic anhydrogossypol; and by the identity of the aniline derivatives produced from the orange crystalline product from ethyl acetate and authentic anhydrogossypol. One of the laboratories of the Southern Utilization Research and Development Division. Agricultural Research Service, U. S. Department of Agriculture.