The identification of ipuranol and some allied compounds as phytosterol glucosides / by Frederick B. Power and Arthur H. Salway.

  • Power, Frederick B. (Frederick Belding), 1853-1927
Date:
[1913?]
Catalogue details

Licence: Public Domain Mark

Credit: The identification of ipuranol and some allied compounds as phytosterol glucosides / by Frederick B. Power and Arthur H. Salway. Source: Wellcome Collection.

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    I. Ipuranol (m. p. 290—295°). A typical specimen of this substance had the following composition: 0*1147 gave 0*3039 C02 and 0*1084 H20. C = 72*3; H = 10*5. The formula originally assigned to ipuranol, namely, C23H40O4, requires 0 = 72*6; H = 10*5 per cent. Sitosterol glucoside, C33H50O6, requires 0 = 72*3; H = 10*2 per cent. Half a gram of the substance was dissolved in 30 c.c. of hot amyl alcohol, and 10 c.c. of an aqueous 15 per cent, solution of hydrogen chloride added, together with sufficient ethyl alcohol to form a homogeneous liquid. After heating for two hours in a reflux apparatus, steam was passed through the mixture to remove the amyl alcohol, and the contents of the flask then filtered. A solid substance was thus collected, which, when crystallised from a mixture of alcohol and ethyl acetate, separated in glistening leaflets melting at 136°. This substance gave the phytosterol colour reaction, and it evidently belonged to that class of compounds: 0*1041 gave 0*3204 C02 and 0*1127 H20. 0 = 83*9; H=12*0. C27H460 requires 0 = 83*9; H = ll*9 per cent. The aqueous acid liquid, from which the phytosterol had been separated by filtration, was exactly neutralised with sodium carbon¬ ate, evaporated to dryness, the residue digested with absolute alcohol, and the mixture filtered. On evaporating the alcoholic filtrate a small amount of a syrupy residue was obtained, which reduced Fehling’s solution, and yielded an osazone melting and decomposing at 212°. It was thus evident that the sugar consisted of dextrose. The original compound had thus become resolved by hydrolysis into a phytosterol and dextrose, according to the equation: c83hm0„+h2o=c27h46o + C6H12O0. II. Ipuranol (m. p. 280—285°). This specimen of the substance was obtained from a different source from the preceding one, and it gave on analysis the following result: 0*0973 gave 0*2573 C02 and 0*0918 H20. 0=72*1; H = 10*5. C33H6606 requires 0 = 72*3; H = 10’2 per cent. Half a gram of this substance was hydrolysed in the manner above described, when it yielded a phytosterol, which separated in glistening leaflets, melting at 136°. This was analysed, and its specific rotatory power determined: 0*0911 gave 0*2800 C02 and 0*1002 H20. 0-83*8; H = 12*2. C27H4C0 requires C = 83*9; H —11*9 per cent. 0*2G49 of anhydrous substance, made up to 20 c.c. with chloro¬ form, gave aD — O^fi7 in a 2-dcm. tube, whence [a]D —35*2°.