The synthetical preparation of the d-glucosides of sitosterol, cholesterol, and some fatty alcohols / by Arthur H. Salway.
- Salway, Arthur H. (Arthur Henry)
- Date:
- [1913?]
Licence: Public Domain Mark
Credit: The synthetical preparation of the d-glucosides of sitosterol, cholesterol, and some fatty alcohols / by Arthur H. Salway. Source: Wellcome Collection.
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![was therefore dissolved in hot alcohol, and the solution digested for about a minute with an excess of potassium hydroxide. In this manner the acetyl groups of the glucoside were eliminated without affecting the remaining part of the molecule, and the free glucoside, which is only sparingly soluble in hot alcohol, was deposited. This was collected, washed with hot alcohol, and purified by crystallisation from a mixture of pyridine and alcohol, when it separated in rosettes of small, colourless needles. When heated in a capillary tube, the substance begins to soften at about 270°, and melts and decomposes at 295—300°. The yield of pure substance amounted to 4 grams : 0-1028 gave 0-2721 C02 and 0'0960 H20. C-72'2; H = 10’4. C33H5gOg requires C = 72 3; H = 10'2 per cent. Sitosterol-d-glucoside, C27ll450,C6H1105, is insoluble in water and only sparingly soluble in alcohol, ether, chloroform, or benzene. It dissolves readily in pyridine, and can be easily crystallised from this solvent in admixture with alcohol. It yields the characteristic colour reaction of the phytosterols when dissolved in acetic anhydride and chloroform, and a drop of concentrated sulphuric acid then added. When heated with aqueous hydrochloric acid in the presence of amyl alcohol it is readily resolved into its components, sitosterol and dextrose. Tetra-a cetyl sitosterol-d-glucoside, C27H450*CGII705Ac4.—This sub¬ stance was prepared by heating the glucoside for thirty minutes with an excess of acetic anhydride. The greater part of the latter was then removed by distillation, alcohol added to the residue, and the crystalline solid which separated then recrystallised from alcohol. It was thus obtained in colourless, glistening leaflets, melting at 166—157°: 0-1010 gave 0-2540 C02 and 0-0812 H20. C-68-6; H-8’9. C41HG4O10 requires C = 68*7; II = 8*9 per cent. 05694, made up to 20 c.c. with chloroform, gave aD —1°18/ in a 2-dcm. tube, whence [a]D — 229°. Tetra-acetylsitosterol-<7-glucoside is very readily soluble in ether, chloroform, benzene, or hot alcohol, but only sparingly so in cold alcohol. It is immediately hydrolysed in the presence of alkali hydroxides with regeneration of the glucoside. Tetrabenzoylsitosterol-d-glucoside, C27H450*CGH705Bz4.-—In order to obtain this compound, sitosterol-c?-glucoside was dissolved in pyridine, and the solution gently warmed for about a minute with an excess of benzoyl chloride. The mixture was then poured into alcohol, when the benzoyl derivative separated as a flocculent pre¬ cipitate. This was collected and purified by crystallisation from](https://iiif.wellcomecollection.org/image/b30620375_0006.jp2/full/800%2C/0/default.jpg)
