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.
8/26 page 562
![other hand, the constitution of chaulmoogric acid were to be represented by the formula: CH0 CH-C[CH2]12-C02H ch,-ch2 it will be seen that the formation of these products can readily be explained. The second dihydroxydihydrochaulmoogric acid will then have the following structure, cn(OH)'cn2>c(OH)rcH^'co^H’ 2 2 and on further oxidation could yield the hypothetical compounds repre¬ sented above, and, consequently, the ketodicarboxylic acid, Cl7H30O5, and formic acid. The ketodicarboxylic acid, C18H3205, obtained by the oxidation of the acids produced by removing the elements of hydrogen bromide from ethyl bromodihydrochaulmoograte, was at first thought to have been derived from the c?/cfopentene structure deduced for chaulmoogric acid, and therefore to have the formula C02H-[CH2]s-C0-[CH„]12-C02H, which would give succinic acid on further oxidation. It was found, however, that, instead of succinic acid, oxalic, formic, and acetic acids were formed, and from these facts the formula C02H-CH2-CHMe-C0[CH2]12-C02H may be deduced. This acid can be considered to have been formed by the following reactions : CH2 + HBr CIL -HBr ch-c[ch2]12.co2h ch2-ch2 CH--CBr[CH2]12C02H CH2-CH2 CHc C02H-CH2*CH-C0LCH2]12-C02H. CH3 + 30 CH-C[CH2]12C02H ch2-ch Dihydrochaulmoogric acid may therefore be considered a mixture of a-carboxy-n-dodecylcyc\opentane and \-a-carboxy-n-dodecyl-2-7)iethyl- cyclo butane. From the foregoing considerations it is seen that the behaviour of chaulmoogric acid can be explained by assigning to it both the follow¬ ing formulae : CH CH0 CH CH[CH2]12-C02H — CH-C[CH2]12-C02H. ch2*ch2 l-a-Carboxy-n-dodeci/l-A*-cydopentcne, 1-a-Carboxy-n-dodecyl-l : i-hicyclopentane. ch2-ch2](https://iiif.wellcomecollection.org/image/b30611751_0008.jp2/full/800%2C/0/default.jpg)
