Abstract
IN 1940 we described the conversion of equilin, through 7-ketoœstrone, 7-hydroxyœstrone and 7-chloroœstrone, to its Δ6 double bond isomer1. The specific rotation [α]D24 of this compound was then reported by us as +150° (in dioxane). Dr. St. Kaufmann, of Syntex, S.A., has kindly directed our attention to the widely divergent value (−127°) given by an otherwise apparently identical preparation obtained in that Laboratory from Δ4-androstenedione (cf. preceding communication by Rosenkranz et al.). A check determination now carried out on a small reference sample of Δ6-isoequilin still in our possession gave −120°, in fair agreement with the value of Rosenkranz et al. This preparation (m.p. 258–261°, corr.) did not depress the melting point of a specimen of 6-dehydroœstrone obtained from Dr. Kaufmann which in our hands melted at 257–260°; likewise, the melting point of a mixture of the respective 3-benzoates (m.p. 201°, 200°) was not depressed. It is clear, therefore, that the positive rotation figure originally recorded by us was in error, and that the two compounds in question are identical in every respect.
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Pearlman, W. H., and Wintersteiner, O., J. Biol. Chem., 132, 605 (1940).
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PEARLMAN, W., WINTERSTEINER, O. Rotation of Δ6-isoEquilin (6-Dehydroœstrone): a Correction. Nature 165, 815 (1950). https://doi.org/10.1038/165815a0
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DOI: https://doi.org/10.1038/165815a0
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