The constituents of the rhizome of Apocynum androsaemifolium / by Charles W. Moore.

  • Moore, Charles Watson.
Date:
1909
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constituents of the rhizome of Apocynum androsaemifolium / by Charles W. Moore. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    composition, but all attempts to separate them by fractional crystal- lisation were unsuccessful. The entire mixture was therefore heated with acetic anhydride, after which the acetylated product was sub- mitted to fractional crystallisation from ethyl acetate. Although by this means the separation was far fx’om complete, the isolation of two pure substances was effected. Isolation of a New Moiiohydric Alcohol, Androsterol, CgoH^g’OH, One hundred grams of the above-mentioned acetylated product were repeatedly crystallised from ethyl acetate, when a small fraction (5 grams) was eventually obtained, which melted constantly at 212—214°, and appeared to be a pure substance. This substance was hydrolysed by boiling with an excess of a 10 per cent, alcoholic solution of potassium hydroxide for four hours. The solvent was then removed, water added, and the resulting solid crystallised from a mixture of ethyl acetate and alcohol, from which it separated in small, colourless needles melting at 208—210° : 0-3350, dried at 115°, lost 0-0130 HgO, HoO = 3-9. 0-1452 of anhydrous substance gave 0-4488 CO, and 0-1538 HoO. C = 84-3 ; H = ll-7. C3oH-oO,HoO requires H2O = 4-0 per cent. C30H50O requires C = 84-5 ; H = ITT per cent. This compound is evidently a monohydric alcohol of the formula OgoH^g’OH. As it does not agree in its properties with any substance of this formula Avhich has hitherto been described, it is proposed to designate it androsterol, with reference to the speciBc name of the plant from which it has been obtained. A determination of its specific rotatory power gave the following result: 0-2060, in 20 c.c. of chloi’oform, gave + 0°37' in a 2-dcm. tube, whence [a]i,-1-29-9°, If to a solution of androsterol in acetic anhydride a few drops of concentrated sulphuric acid ai-e added, a fine magenta-red colour slowly develops, which is permanent for several hours. Monoacetylandrosterol, CggH^gO-CO'CHg.—On heating androsterol with acetic anhydride, the pure acetyl derivative, melting at 212—214°, was regenerated. When crystallised from ethyl acetate, it separates in long, fine needles : 0-1252 gave 0-3760 COg and 0-1250 HjO. 0 = 81-9; H = ll-1. CggHjgOg requires 0 = 820; H = ll-1 percent. A determination of its specific i-otatory power gave the following result: