Abstract
CRYSTALLINE bilirubin changes with time as noted by Küster1. Newly recrystallized, it dissolves immediately and completely in chloroform. With aged preparations, when dissolved at room temperature, a certain amount of insoluble substance is observed which dissolves within a few seconds when boiled under reflux. This must be due to either an isomerization from bilirubin to dihydrobiliverdin—a displacement of the π electrons from the vinyl to the central methylene bridge2—or a transition between two crystalline phases, the less soluble having the highest thermodynamical stability.
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References
Küster, W., Hoppe-Seyler's Z., 59, 63 (1909).
Gray, C. H., Bile Pigments in Health and Disease, 16 (Charles C. Thomas, Publ., Springfield, Illinois, 1961).
Fog, J., and Jellum, E., Nature, 198, 88 (1963).
Lemberg, R., and Legge, J. W., Hematin Compounds and Bile Pigments (Interscience Publ., London, 1949).
Fog, J., Diss., Oslo (1960).
Schellong, G., Ikterus Neonatorum, 49 (Thieme Verlag, Stuttgart, 1962).
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FOG, J., BUGGE-ASPERHEIM, B. Stability of Bilirubin. Nature 203, 756–757 (1964). https://doi.org/10.1038/203756a0
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DOI: https://doi.org/10.1038/203756a0
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