The stability of 13,14-dihydro-15 keto-PGE2

13,14-Dihydro-15 keto-PGE2 decomposes by first order reaction kinetics, dependent on pH, temperature and albumin concentration. Under common experimental conditions at or near neutrality in the absence of albumin decomposition is suspended with the formation of 13,14-dihydro-15-keto-PGA2. Cyclization into 11-deoxy-13,14-dihydro-15 keto-11,16-bicyclo-PGE2 occurs at elevated pH in purely aqueous buffers, and also at or near neutrality in the presence of albumin. Albumin accelerates, quantitatively, the decomposition of 13,14-dihydro-15 keto-PGE2 and promotes, qualitatively, the formation of the bicyclo rearrangement product. High performance liquid chromatographic analysis indicates that the cyclization product exists in at least three epimerically distinct forms. The two major epimers have been synthesized and isolated in pure form. They differ, mainly, by their optical rotation.