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?]
Catalogue details

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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    myricyl-d-glucoside. The glucoside was obtained, after being crystallised from methyl alcohol, in small, hexagonal plates, melting at 94°. The yield of pure substance amounted to about 10 per cent, of the ceryl alcohol employed: 01460 gave 0'3808 C02 and 0-1560 H20. 0 = 711; H = 11‘9. C33H6606 requires C = 71'0; H = 11'8 per cent. Ceryl-d-glucoside was found to exist in two modifications, the one melting at 94°, as described above, whilst the other melts at 135°. The latter was obtained by dissolving the former in hot chloroform, when glistening leaflets of the modification of high melting point immediately separated from the hot solution. If the latter is recrystallised from alcohol, it is more or less transformed into the modification of lower melting point. The glucoside melting at 135° was analysed, with the following result: 0 0871 gave 0-2263 C02 and 0-0928 H20. C = 70'9; H = ll*8. C33H6606 requires C = 71‘0; 11 = 11 8 per cent. Tetra-acetylceryl-d-glucoside, C27H550*C6H706Ac4. — This com¬ pound was prepared in the manner described in connexion with the preparation of tetra-acetylmyricyl-d-glucoside. It crystallised from a mixture of alcohol and ethyl acetate in small, colourless leaflets, melting at 85—87° : 0-0758 gave 0-1883 C02 and 0'0696 H20. C = 67‘8; H = 102. C41H74O10 requires C = 67-8; H = 10'2 per cent. 0 2010, made up to 20 c.c. with chloroform, gave aD — 0°17/ in a 2-dcm. tube, whence [a]D —141°. V. Cetyl-d-glucoside, C16H330,C6H1105. This glucoside has already been described by Fischer and Helferich {loc. cit.). In the present investigation it was prepared by the method of these authors, but a more expeditious way of isolating the product was adopted. Five grams of cetyl alcohol were shaken for eight hours in dry ethereal solution with bromo- acetoglucose (5 grams) and dry silver oxide (5 grams). The mixture was then filtered to remove the silver, the ethereal filtrate evaporated, and the residue from the latter hydrolysed in alcoholic solution by heating for about a minute with an excess of potassium hydroxide. Water was then added to the alcoholic liquid, and the precipitated solid extracted with ether. On washing the ethereal solution with water and thus removing the alcohol contained in it, the glucoside separated as a flocculent precipitate, which was collected and crystallised from chloroform. It was thus obtained in small, colourless needles, which began to soften at 78°, and com¬ pletely melted at about 150°. It yielded an acetyl derivative,