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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    0'3025, in 20 c.c. of chloroform, gave ajD + l°15' in a 2-dcm. tube, -whence [a]D + 41'3°. Monobromoacetylandrosterol, C3QH^gBrO'CO*CH3.—One gram of acetylandrosterol was dissolved in 50 c.c. of chloroform, and to the cold solution a 5 per cent, solution of bromine in the same solvent was added, drop by drop, until a slight excess of bromine was pi-esent. The liquid, which evolved hydrogen bromide, was then at once shaken with a solution of sodium hydrogen sulphite, washed with water, dried, and the solvent removed. A syrup was thus obtained which, after treatment with ethyl acetate, yielded a crystalline product. The latter, after repeatedly crystallising from the same solvent, separated in colourless prisms, melting at 228—230°, and amounted to 0'6 gram; 0-1494 gave 0-3850 CO2 and 0-1270 H,0. C - 70-3 ; H = 9-4. 0-1570 „ 0-4026 CO2 „ 0-1325 h“o. C = 69-9; H = 9-3. ’0-2614 „ 0-0906 AgBr. Br=14-7. CggHj^OoBr requires 0 = 70-2 ; H = 9-3 j Br= 14-6 per cent. This substance is evidently a ??io»io6ro??m-derivative of acetyl androstei’ol. Isolation of a New Monohydric Alcohol, Homoandrosterol, CgyH^g'OH. Some of the numerous mother liquors obtained dui-ing the separa- tion of the above-described acetyl derivative of androsterol (m. p. 212—214°) deposited on standing small amounts of sparingly soluble, prismatic needles, which, after recrystallisation from ethyl acetate, melted constantly at 234—236°. The amount of this substance was 2 grams, and its properties indicated that it was a pure compound. It was hydrolysed by boiling for four hours with an excess of a 10 per cent, alcoholic solution of potassium hydroxide, the solvent removed, water added, and the resulting solid recrystal- lised from dilute alcohol, from which it separated in small, colourless needles melting at 192° : 0-1201 gave 0-3702 CO2 and 0-1270 HgO. C = 84-0; H=ll-7. 03711^40 requires 0 = 84-4; H= 11-4 per cent. This compound is evidently a monohydric alcohol of the formula ■^27H4s'^H. As it does not agree in its properties with any substance of this formula which has hitherto been described, and differs from androsterol by the elements CgHg, it is proposed to designate it homoandrosterol. If to its solution in acetic anhydride a drop of concentrated sulphuric acid is added, a magenta-red colour is at once produced, which is permanent for several hours. Honoaceiylhomoandrosterol, C27H4gO-CO*CHg.—On heating homo-