The constituents of the seeds of Hydnocarpus wightiana and of Hydnocarpus anthelmintica : isolation of a homologue of chaulmoogric acid / by Frederick Belding Power and Marmaduke Barrowcliff.

Frederick Belding Power

Date:: [1905]

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constituents of the seeds of Hydnocarpus wightiana and of Hydnocarpus anthelmintica : isolation of a homologue of chaulmoogric acid / by Frederick Belding Power and Marmaduke Barrowcliff. 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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$tallisation from ethyl alcohol, formed glistening needles melting at 132—133°. 0-0266 gave 0-0812 COg and 0-0292 H2O. C = 83-3 ; H = 12-2. requires C = 83-9 ; H = ll-8 per cent. The colour reactions of this substance confirmed its identity as phytosterol. The Fatty Acids. The potassium salts obtained by the above hydrolysis -were dissolved in water, the liquid acidified with sulphuric acid, and the liberated fatty acids taken up by ether. The ethereal solution was then washed, dried, and the ether removed, the last traces of the latter being eliminated by heating the residual oil at 100° for some time. On cooling, a hard, white cake was obtained, representing the total fatty acids. These gave the following values; melting point, 41 — 44°; [a]i, in chloroform + 60-4°; acid value, 214-0 ; iodine value, 106-3. For the investigation of the mixture of fatty acids, 1000 grams of the fat were hydrolysed, the aqueous solution of the potassium salts acidified, and the solid cake of acids collected, washed with water, drained at the pump, and then dried between filter paper. The aqueous filtrate from the fatty acids was distilled in steam, and from the acid distillate a barium salt was prepared. The latter was very small in amount and consisted of the salts of acetic and butyric acids. The solid mixture of acids was fractionally crystallised from alcohol. The first crystalline crop which separated from the alcoholic solution of the whole of the acids from the 1000 grams of fat weighed 200 grams and melted at 46—48°. On further crystallisation, however, from alcohol and from ethyl acetate, it was obtained in the form of glisten- ing leaflets having the constant melting point of 67—68° and giving the following results on analysis : 0-0792 gave 0 2230 CO.^ and 0-0810 H^O. (J = 76-8; H=ll-4. 0-1030 „ 0-2904 CO2 „ 0-1056 HgO. C = 76-9 ; H = 11-4. CJJ.H32O2 requires C = 77-1 ; H = 11-4 per cent. 0- 1412 absorbed 0-1270 iodine. 1 = 90-0. ^18^32^2’ 01^6 ethylenic linking, requires 1 = 90-6 per cent. 1- 2032, in alcohol, required NaOH equivalent to 42-7 c.c. of a deci- normal solution, wliich is the c.alculated amount for CjgHg202. A solution of 1-8127 in chloroform, made up to 25 c.c., gave in a 1-dcm. tube oj, -t-4°15', whence [a]u 4-58-6°. It was thus shown that this acid melting at 67—68° was in all respects identical with chaulmoogric acid, first obtained by Power and Gornall {loc, cit.) from chaulmoogra oil (from the seeds of Taraktogenos Kurzii, King).$