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.

  • Power, Frederick B. (Frederick Belding), 1853-1927.
Date:
[1905]
Catalogue details

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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    46—47°; (4) 53—55°; (5) 56—58°. Fraction (2), on recrystallisa- tion from alcohol, gave chaulmoogric acid melting at 67—68°. Fractions (4) and (5) were combined and recrystallised from alcohol. The recrystallised acid then melted at 59—60°, was in the form of lustrous leaflets, and, on further crystallisation from alcohol or ethyl acetate, its melting point remained unchanged. 0-1018 gave 0-2833 COg and 0-1022 HgO. C = 75-9 ; H = ll-2. 0-1056 „ 0-2945 COg „ 0-1052 HgO. C = 76-l ; H = 1M. C^gHggOg requires 0 = 76-2; H = 1T1 per cent. 0-3749 required NaOH equivalent to 14-8 c.c. of a decinormal solu-. tion, which is the calculated amount for C^^gHggOg. 0-2608 absorbed 0-2612 iodine. 1 = 100-2. CjgHggOg, with one ethylenic linking, requires 1 = 100-7 per cent. The silver salt was prepared and analysed : 0-2724 gave 0-0815 Ag. Ag = 29-9. 0-1700 „ 0-3296 COg, 0-1138 HgO, and 0-0510 Ag. 0 = 52-9; H = 7-4; Ag = 30-0. CigHg^OgAg requires C = 53'5 ; H = 7-5 ; Ag = 30-1 per cent. It was thus shown that this acid, melting at 59—60°, has the formula OioHggOg, contains only one ethylenic linking, and therefore must possess a closed carbon ring. In other vrords, it is a lower homologue of chaulmoogric-acid, and belongs to the same type as the latter. We have designated this new acid hydnocarpic acid. Hydnocarpic acid, like chaulmoogric acid, is optically active. A solution of 1-3063 in chloroform, made up to 25 c.c., gave in a 1-dcm. tube aj, -f 3°34', whence [a]n -f 68-1°. Hydnocarpic acid is only sparingly soluble in the cold in the usual organic solvents, with the exception of chloroform, in which it is easily soluble. An aqueous solution of its sodium salt at once decolorises permanganate in the cold. Like chaulmoogric acid, it remains un- attacked by fused potassium hydroxide, even at 250°. The following derivatives of the acid were prepared and characterised. Methyl Hydnocarpate, C^jHg^'COgMe. Five grams of hydnocarpic acid were dissolved in 25 c.c. of methyl alcohol and 5 grams of sulphuric acid slowly added, when the ester soon separated as an oil. After the mixture had been allowed to stand for some hours, water was added, the oil taken up with ether, the ethereal solution washed with sodium carbonate, then with water, dried, the ether removed, and the ester distilled under diminished pressure.