Chemical examination of cotton-root bark / by Frederick B. power and Henry Browning, Jun.

  • Frederick Belding Power
Date:
1914.]
Catalogue details

Licence: Public Domain Mark

Credit: Chemical examination of cotton-root bark / by Frederick B. power and Henry Browning, Jun. Source: Wellcome Collection.

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    199°, whereas nothing could be isolated from the non-phenolic product. Isolation of a New, Phenolic Substance, C9H80(0H)2. The ethereal extract of the aqueous liquid (A), which had been shaken with aqueous ammonium carbonate, was next extracted with successive small amounts of aqueous sodium carbonate, the strength of the latter being gradually increased from 1 to 10 per cent. The first four extractions yielded a product which, after fractional crystallisation from dilute alcohol, separated in nearly colourless needles, melting at 258- 260°, and amounting to 0'34 Gm. The substance was not readily soluble in cold alcohol, acetone, chloroform, or methyl alcohol, but dissolved readily in pyridine. It dissolves in aqueous potassium hydroxide, forming a bright yellow liquid, and its solution in aqueous alcohol gives with ferric chloride a purple colour. The substance, dried at 105°, was analysed, and its mole¬ cular weight determined hy the microscopic method, with the following results:— 0 0596 gave 01416 C03 and 0-0331 H20. C = 64 8; H = 6 2 0 0737 „ 01754 C03 „ 0‘0435 H20. C = 64 9; H = 6;6 0 0454, in 5 Cc. of pyridine, was between 0'06 and 0058 mol., using benzil as the standard. Mean M.W. = 154. C9H10O3 requires C = 651; H = 6'0 per cent. M.W. = 166. An acetyl derivative of the substance was prepared by dis¬ solving 0'09 Gm. in a little pyridine, and gently boiling for an hour with acetic anhydride. The liquid was then concen¬ trated and shaken with water, the substance which thus sepa¬ rated being collected, dissolved in ether, and the solution washed with aqueous sodium carbonate. After removing the ether the acetylated compound was crystallised from alcohol, when 005 Gm. of small, tabular crystals were obtained, which melted at 152°. 0-0491 gave 0-1120 C02 and 0-0274 H20. C - 62‘2 ; H = 6‘2. C9H80(0.C0.CH3)a requires C = 62'4; H =5 6 per cent. A further small amount (006 Gm.) of the substance was converted into a benzoyl derivative by boiling for half an hour with benzoyl chloride and a little pyridine. The product was cautiously treated with hot water, and then a current of steam passed through the liquid, when, after crystallisation from alcohol, colourless microscopic crystals were obtained, melting at about 155°. A consideration of these results indicates the above-described substance to be a new dihydric alcohol, possessing the formula C9H1003, but the amount available was not sufficient for its further investigation.
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