Twenty‐four oxygenated cholesterols and structurally related compounds were analyzed by high performance liquid chromatography with silicic acid column and various mobile phases. Hexane–propanol was superior to hexane/tetrahydrofuran and hexane/ethyl acetate for the separation of oxygenated cholesterols. The retention volumes of oxygenated cholesterols depended on the characteristics of the substituting group, its position of substitution, as well as its orientation. The effect of various functional groups at different positions on cholesterol molecules, in general order of decreasing retention volumes, were: hydroxy on the ring, carbonyl on the ring, epoxy on the ring, hydroxy on the side chain, and carbonyl on the side chain. Synergistic effect of multiple hydroxyl substitutions on cholesterol was observed.
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Tsai et al. (1981) studied this question.
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