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.
11/26 page 565
![steam passed through the liquid in order to remove any volatile acid. The distillate was found to contain a small amount of formic acid, which was identified by the usual tests and by the analysis of its barium salt: 0*3002 gave 0*3060 BaS04. Ba = 60*0. (C02H)2Ba requires Ba=60*4 per cent. This acid was evidently produced by the further oxidation of one of the dihydroxydihydrochaulmoogric acids subsequently described. The non-volatile acids remaining in the distilling flask were extracted, and converted into their methyl esters by treatment with methyl alcohol and sulphuric acid. The product was then distilled under a pressure of 16 mm., when the following fractions were collected : 200—220°; 220—245°; 245—260°; 260—275°; 275—290°/16 mm. There then remained in the flask a quantity (22 grams) of an undistill able oil, which apparently consisted of condensation products. Fraction 200—220°/16 mm.—This was analysed with the following result: 0T030 gave 0*2519 CO, and 0*0964 H20. C = 66*7; H = 10*4. Ci6H30O4 requires C = 67*l; H=10*5 per cent. It evidently consisted chiefly of the methyl ester of w-dodecanedi- carboxylic acid, C16H30O4, which was obtained in larger quantity by the oxidation of chaulmoogric acid with an excess of permanganate, and its identity established. Fractions 220—245° and 245—260°/16 mm.—These were small in amount, and were found to consist of mixtures of the constituents of the fractions of lower and higher boiling point. Isolation of Two Dihydroxydihydrochauhnooqric Acids, C]7Hsl(0H)2-C02H. Fraction 260—275°/16 mm.—This was the largest fraction obtained. On cooling, it deposited a considerable quantity of a solid substance, which was brought on a porous plate to remove adhering oil, after which it melted at 60—68° : 0*0933 gave 0*2366 C02 and 0*0910 H20. C = 69*2; H = 10*8. C19H30O4 requires C = 69*5 ; II = 11 *0 per cent. This substance agreed in composition with a methyl ester of di¬ hydroxydihydrochaulmoogric acid. After several crystallisations from methyl alcohol it yielded an ester crystallising in long, glistening needles, which melted at 75—76°, and this melting point was not changed by further crystallisation : 0*1056 gave 0*2669 CO, and 0*1045 H20. C = 68*9; H = 110. C17H31(0H)2*C02Me requires C = 69*5 ; H = 1T0 per cent.](https://iiif.wellcomecollection.org/image/b30611751_0011.jp2/full/800%2C/0/default.jpg)
