Abstract
MEASUREMENTS recently carried out on mono-molecular films of β- and γ-oleananic acids and esters1 show that these compounds occupy areas very much smaller than those which are calculated on the basis of Haworth's triterpene formula (I), the limiting values for the two acids being 52 and 45 sq. A. respectively. In these two compounds there are no water-attracting groups, apart from the carboxyl group, which could be responsible for the effects observed, as in oleanolic acid itself2; the results suggest that the carboxyl group must occupy a position in one of the terminal rings. Of the possible formulations, the structure (II) for oleanolic acid satisfies the principal requirements.
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References
Jacobs and Fleck, J. Biol. Chem., 96, 341 (1932).
Askew, J. Chem. Soc., 1585 (1936).
Bilham and Kon, J. Chem. Soc., 1469 (1940).
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BILHAM, P., KON, G. Position of the Carboxyl Group in Oleanolic and Related Acids. Nature 147, 745 (1941). https://doi.org/10.1038/147745b0
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DOI: https://doi.org/10.1038/147745b0
