The constituents of cluytia similis / by Frank Tutin and Hubert W.B. Clewer.
- Tutin, Frank.
- Date:
- [1912?]
Licence: Public Domain Mark
Credit: The constituents of cluytia similis / by Frank Tutin and Hubert W.B. Clewer. Source: Wellcome Collection.
11/18 page 2229
![not agree in its properties with any compound previously described, it is proposed to designate it cLuytiasterol. Its optical activity was determined with the following result: 0'2853,* made up to 20 c.c. with chloroform, gave aD —1°30/ in a 2-dcm. tube, whence [a]D — 52‘6°. Examination of the Fatty Acids. The alkaline aqueous liquid from which the unsaponifiable matter had been removed, as above described, was acidified, and distilled with steam, but the amount of volatile acid removed was negligible. The mixture was then extracted with ether, when a small amount of an undissolved solid was collected. The latter crystallised from alcohol in needles melting at 248°, and yielded an acetyl derivative melting at 255°, but the amount obtained was too small for further examination. The dark green, ethereal solution containing the fatty acids was then evaporated to a small bulk and treated with a large volume of petroleum (b. p. 35—50°), when the greater part of the chlorophyll was precipitated. The clear petroleum solution was then decanted, evaporated, and the residual fatty acids converted into their methyl esters and distilled, when a quantity (21 grams) of a liquid was obtained. The latter was mixed with the 16 grams of esters previously isolated, and the whole fractionally distilled several times under GO mm. pressure, when the following fractions were obtained: (i) —240°; (ii) 240—250°; (iii) 250—260°; (iv) 260—270°; (v) 270—280°; (vi) 280°+. Fraction (i) solidified on cooling, and was found to consist of methyl palmitate, since it yielded palmitic acid (m. p. 63°) on hydrolysis. (Found, C = 74'7; H = 12‘5. Calc., C = 75*0; H = 12,5 per cent.) Fractions (ii) and (iii), when hydrolysed, yielded a small amount of a mixture of unsaturated acids, but the greater part of the material was a mixture consisting essentially of palmitic and stearic acids. (Found, C = 75‘2; H = 12’6. Calc., for C16H3O02, 0 = 75-0; H = 12'5 ; for C^H^O*, C = 76*l; H = 12'7 per cent.) Fraction (iv) became partly solid on keeping. On hydrolysis it yielded a further quantity of the previously-described new fatty acid, cluytinic acid, C2iH4202, which was identified by its melting point (69°) and by analysis. (Found, C = 77'3; H = 131. Calc., C = 773; H = 12'9 per cent.) Fraction (v) was too small for examination, but fraction (vi), after being hydrolysed and freed from traces of unsaponifiable matter, yielded an acid melting at 74°. The amount of the latter, however, was too small for investigation. * Dried at 110°.](https://iiif.wellcomecollection.org/image/b3061952x_0011.jp2/full/800%2C/0/default.jpg)
