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Self-transesterification of castor oil was employed to prepare higher molar mass polyols possessing interesting properties that can be used without purification. The resulting structure of the polyols is complex due to the reversible nature of transesterification reaction, allowing formation and destruction of new polyols simultaneously. Detailed structures of the prepared polyols were studied using spectrometric analysis including MALDI-TOF, that enables identification of the anticipated structures, supporting the proposed mechanism. In addition, polyurethane elastomers were prepared from these polyols, and yielded soft materials with low Shore A hardness. These polyols were also tested in molded polyurethane foams and their polyurethane properties were compared with those of commercial bio-polyols. [ABSTRACT FROM AUTHOR]