The constituents of the bark of Prunus serotina : [isolation of 1-mandelonitrile glucoside] / by Frederick B. Power and Charles W. Moore.

  • Frederick Belding Power
Date:
[1909]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constituents of the bark of Prunus serotina : [isolation of 1-mandelonitrile glucoside] / by Frederick B. Power and 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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    Isolation of \-Mandelic Acid. A quantity (400 grams) of the previously-mentioned aqueous liquid was diluted with water to the measure of 1 litre, 50 grams of sulphuric acid added, and the mixture boiled for six hours. It was then subjected to distillation with steam, when the distillate was found to contain small amounts of furfuraldehyde, benzaldehyde, and benzoic acid. The aqueous, acid liquid remaining in the distillation flask, after being allowed to cool, was filtered, and extracted twelve times with ether. The ethereal liquid from the first extraction was discarded as being likely to contain a little benzoic acid. All the subsequent extractions were united, and the solvent removed, when a residue was obtained which was mixed with 50 c.c. of water. On allowing the liquid to stand for some time, a quantity of /3-methylaesculetin was deposited, which was removed by filtration, and the strongly acid, aqueous tilti-ate ex- tracted five times with ether. The ethereal liquid was then repeatedly extracted with small quantities of a dilute solution of ammonium carbonate until the aqueous liquids just began to show an alkaline reaction. The combined ammonium carbonate extracts were acidified with hydrochloric acid and extracted with ether, when about 3 grams of a crystalline substance were obtained, melting at 128—130°. After recrystallisation from benzene, it melted at 130—133°: 0T238 gave 0-2880 C02 and 0-0624 H20. C = 63-4; H = 5-6. The substance was again crystallised from benzene, when it melted at 132—133°, and was again analysed : 0-1276 gave 0-2965 C02 and 0*0635 H20. C = 63'4; H = 5-5. CgHgOg requires C = 63'2; H = 5-3 per cent. 0-3710, dissolved in 20 c.c. of water, gave in a 2-dcm. tube aD — 5°44', whence [a]D - 154-5°. The substance was thus identified as ^-mandelic acid, and its isolation from the aqueous liquid, after hydrolysis, afforded evi- dence of the presence of either amygdalin or Z-mandelonitrile glucoside. Isolation of l-Mandelonitrile Glucoside. One kilogram of the original alcoholic extract, representing about 3'8 kilograms of the bark, was mixed with 2 litres of water, and the volatile constituents were removed by distillation with steam. The contents of the distillation flask were then filtered while hot from the previously-described green resin, the latter being thoroughly washed with water, and the washings added to the filtrate. After allowing the combined aqueous filtrate and washings to stand for