The constitution of chaulmoogric and hydnocarpic acids / by Marmaduke Barrowcliff and Frederick B. Power.
- Barrowcliff, Marmaduke.
- Date:
- [1907]
Licence: In copyright
Credit: The constitution of chaulmoogric and hydnocarpic acids / by Marmaduke Barrowcliff and Frederick B. Power. Source: Wellcome Collection.
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![the hydroxyketo-acid, and may be attributed to keto-enolic tauto- ✓ merism occurring in the following manner : CO CH(0H)CH[CH.J12-C02H CH 2-CH, CH(OH) C-[CH,]12-C0.2H. ch,-ch2 The optically inactive hydroxyketo-acid obtained is therefore pro¬ bably represented by the above formula. The formation of the ketodicarboxylic acid, ClvH30O5, 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]12-C02H -> ch2-ch2 ch<o|h / 125 —> CH(OH) CH2-CH2-CH(0H)[CH2]12-C02H —> HC02H + C02H-[CH2]2-C0-[CH2]12-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 formuke : (I) CH2(0H)'CH(0H)'[CH„]a'C0*[CHJ12-C02H and (II) CH0-[CH2]2-C(0H)*[CH2]12-C02H. “ OH2(OH) 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) CH[CH2]12-C02H CH, -CH,](https://iiif.wellcomecollection.org/image/b30611751_0007.jp2/full/800%2C/0/default.jpg)
