ビタミンD_2散剤の安定性に関する研究(第3報) : ビタミンD_2の新異性体の構造について

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In a previous study, it was found that vitamin D_2 (I) in powders prepared with excipients such as talc or CaHPO_4,which have a high surface acidity, is readily isomerized yielding a new isomer (III) together with isocalciferol (II) and isotachysterol (IV). In this paper, the physicochemical properties of III were determined. Compound III, C_<28>H_<44>O, [α]^<22>_D+40.8° in CHCl_3,was isolated from the other isomers through alumina column chromatography, and was crystallized as a p-phenylazobenzoate, C_<41>H_<52>O_2N_2,mp 152-153°, [α]^<23>_D+359.4° in CHCl_3. III absorbs at 286.5 mμ (ε, 38000) with shoulders both at 276 mμ and 298 mμ in isopropanol. Infrared and nuclear magnetic spectral resonance data, as well as the results of optical rotatory dispersion and circular dichroism suggest that the structure of III is 9,10-secoergostatetraene-(1 : 10,5 : 6,7 : 8,22 : 23)-3α-ol, which is a cis isomer of II. III is redily isomerized to II by iodine and to IV by boron trifluoride, both in n- hexane solutions.
社団法人日本薬学会の論文
1969-07-25