The constitution of chaulmoogric and hydnocarpic acids / by Marmaduke Barrowcliff and Frederick B. Power.

  • Barrowcliff, Marmaduke.
Date:
1907
Catalogue details

Licence: In copyright

Credit: The constitution of chaulmoogric and hydnocarpic acids / by Marmaduke Barrowcliff and Frederick B. Power. 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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    the hydroxyketo-acid, and may be attributed to keto-enolic tauto- merism occurring in the following manner : CO (pH(0H)CH[CH.,]i2-C02H CH, 6h2 C(OH) CH(OH) C-[CH2li2-C02H. CHg—— CH2 The optically inactive hydroxyketo-acid obtained is therefore pro- bably represented by the above formula. The formation of the ketodicarboxylic acid, Cj^HgoOg, remains to be considered. That it cannot have been formed by the further oxida- tion of the tricarboxylic acid is shown by the great stability of this compound towards alkaline permanganate solution. Moreover, as this keto-acid is the only acid obtained which possesses but one atom of carbon less than chaulmoogric acid, its formation is probably accom- panied by the production of the formic acid which occurs amongst the products of oxidation. The formation of these two acids from the formula deduced above for chaulmoogric acid could only be explained in the following manner: CH CH CH[CH2]i2*C02H CH2-CH2 CH<2I^ / |OH —> CH(OH) CH2-CH2*CH(0H)[CH2]i2-C02H HCO2H -f- C02H-[CH2]2-C0*[CH2]i./C02H. Experience has shown, however, that in every instance of the oxida- tion of a compound possessing a ring containing a double linking, the ring opens at that point alone, so that this explanation must be con- sidered improbable. There are two hypothetical acids from which the above mentioned keto-acid and formic acid could have been formed by further oxidation, namely, those possessing the following formulae : (I) CH2(0H)-CH(0H)-[CH2]2-C0-[CH2]i2*C02H and (II) CH0-[CH2]2-C(0H)-[CH2]i2-C02H. CH2(0H) These two hypothetical acids could, however, not be produced from an acid of the formula deduced above for chaulmoogric acid. If, on the CH(OH) CH(OH) CII[CIl2],2-C02H CHg CHg
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