Gynocardin : a new cyanogenetic glucoside / by Frederick B. Power and Frederic H. Lees.

  • Frederick Belding Power
Date:
[1905]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Gynocardin : a new cyanogenetic glucoside / by Frederick B. Power and Frederic H. Lees. 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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    Gynocardin crystallises from water in colourless, glistening, prism- atic needles containing 1J molecules of water of crystallisation, with which it readily parts at a temperature of 115°. The anhydrous substance melts at 162—163° with only slight decomposition, and has the formula C13H19Os)N. It is dextrorotatory, the anhydrous substance having in aqueous solution the specific rotatory power [a]n + 72'5°. Definite proof of the cyanogenetic nature of gynocardin is afforded by the fact that when the enzyme of the seeds, gynocardase, is brought into its aqueous solution, hydrogen cyanide is quickly evolved. Until recently, the only definite cyanogenetic glucoside known was amygdalin, C20H27OnN, which has the constitution C12H21O10-O-CH(C6H5)-CN, and is the maltose ether of benzaldehydecyanohydrin, but, in a series of researches entitled “ Cyanogenesis in Plants,” Dunstan and Henry have isolated and studied three other definite members of this class. They are lotusin, C28H31016N, the lotoflavin ether of maltosecyano- O OH hydrin, C11H21O10‘CH’O‘j//\//\—/ NoH (Phil. Trans., 1901, CN \/\/ OH CO 194, 515) ; dhurrin, C14Hl707N, the dextrose ether of j9-hydroxy- benzaldehydecyanohydrin, C6Hn05-0-CH(CN)*C6H4,0H (Phil. Trans., 1902, 199, 399) ; and phaseolunatin, C10Hl7O6N, the dextrose ether of acetonecyanohydrin, C6H1105'0,C(CH3)2*CN (Proc. Roy. Soc., 1903, 72, 285). It is seen that whereas, on the one hand, amygdalin, dhurrin, and phaseolunatin are sugar 'ethers of the cyanohydrins of substances other than sugars, lotusin, on the other hand, is an aromatic ether of a sugar cyanohydrin. The constitution of gynocardin, the fifth member of the class of cyanogenetic glucosides which has been isolated in a pure condition, being thought of some interest, the elucidation of the question has been attempted. When gynocardin is treated with acetic anhydride and sodium acetate, hepta-acetylgynocardin, C13H1209(C2Hg0)7N, is formed; it crystallises in needles melting at 118—119° and has [a]D +40‘4° in chloroform. A most remarkable property of gynocardin, which brings it into sharp contrast with the other members of its class, is its great stability towards the usual acid hydrolysing agents. Dhurrin, for example, after heating for five minutes with dilute acid, afforded ^-hydroxy- benzaldehyde on extracting with ether, whereas with gynocardin practically no hydrolysis had taken place on heating for half an hour (
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