Most components of the biosphere are continuously ex­ posed to oxygen from the atmosphere. Accordingly, the inex­ orable deterioration of all organic compounds by the slow attack of oxygen must occur. Despite this eventuality, a definitive treatment of oxygen-dependent decomposition of any single important natural product has not heretofore been made. The instant monograph attempts to provide a complete description of the autoxidation of one such impor­ tantnatural product, cholesterol, as the matter is currently understood. The autoxidation of cholesterol in Nature has been a matter of interest to others since the close of the nine­ teenth century and to me for the past three decades. In this monograph I present aspects of what I have learned about cholesterol autoxidation during that interval. Be­ cause of the diffuse ann troublesoae nature of the subject I have selected to cite references to the literature rather fully, so that all items discussed may be properly evaluated by the interested reader. Though such extensive citation of references makes for labored reading, I hope the text will serve as a definitive treatment of the subject from which other studies may be engendered without extensive recourse to the older material. An .attempt has been made to include much related in­ formation so that a detailed awareness of the interrelation­ ships between cholesterol autoxidation and other aspects of chemistry, metabolism, and toxicology may be had. I risk teaching more on the subject than any reader care to learn.

Most components of the biosphere are continuously ex­ posed to oxygen from the atmosphere. Accordingly, the inex­ orable deterioration of all organic compounds by the slow attack of oxygen must occur. Despite this eventuality, a definitive treatment of oxygen-dependent decomposition of any single important natural product has not heretofore been made. The instant monograph attempts to provide a complete description of the autoxidation of one such impor­ tantnatural product, cholesterol, as the matter is currently understood. The autoxidation of cholesterol in Nature has been a matter of interest to others since the close of the nine­ teenth century and to me for the past three decades. In this monograph I present aspects of what I have learned about cholesterol autoxidation during that interval. Be­ cause of the diffuse ann troublesoae nature of the subject I have selected to cite references to the literature rather fully, so that all items discussed may be properly evaluated by the interested reader. Though such extensive citation of references makes for labored reading, I hope the text will serve as a definitive treatment of the subject from which other studies may be engendered without extensive recourse to the older material. An .attempt has been made to include much related in­ formation so that a detailed awareness of the interrelation­ ships between cholesterol autoxidation and other aspects of chemistry, metabolism, and toxicology may be had. I risk teaching more on the subject than any reader care to learn.