The constituents of Gloriosa superba / by Hubert William Bentley Clewer, Stanley Jospeh Green and Frak Tutin.

  • Clewer, Hubert W. B.
Date:
1915.]
Catalogue details

Licence: Public Domain Mark

Credit: The constituents of Gloriosa superba / by Hubert William Bentley Clewer, Stanley Jospeh Green and Frak Tutin. Source: Wellcome Collection.

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    somewhat, and deprived of some phenolic material by means of aqueous potassium hydroxide. On evaporating the dried ethereal liquid, a residue was obtained, which slowly crystallised. The solid so obtained crystallised from ethyl acetate in small, very pale yellow leaflets, melting constantly at 177—178°, which were anhydrous. A further small amount of this base was obtained from the petroleum extract of the resin, as subsequently mentioned, the total amount isolated being about 0'75 gram: 01014 gave 0-2429 CO, and 0-0591 H,0. C = 65*3; H-65. 0-0890 „ 0-2141 CO, „ 0-0540 H20. C = 65-6; H = 6*7. 0*2776 ,, 12*3 c.c. N2 (moist) at 19° and 768 mm. N = 5*2. 0-1198 „ 0-2816 Agl. MeO--=31*0. C^H^N, requires C = 65‘4; XT = 6*3; N = 4*8; 6MeO = 31*7 per cent. C15H1704N requires C = 654; XI = 6*3 ; N = 5*l; 3MeO = 33*8 per cent. The results of the analyses given above agree best with the higher formula, but, owing to the small amount of material avail¬ able, the possibility of the lower formula being the correct one could not be excluded. No gold salt could be obtained from this base, since it readily reduced auric chloride to the metallic state. Isolation of Salicylic, 2-71 yd roxy-6-mcthoa'i/ben zoic and Benzoic A rids.—The ammonium carbonate extracts of the ethereal extract of the aqueous liquid were acidified, and extracted with ether. The crystalline residue obtained on evaporating the ether was dis¬ solved in methyl alcohol, some sulphuric acid added, and the mix¬ ture heated for some time, after which the resulting ester was isolated. Although this process of esterification was repeated several times, the greater portion of the acid remained in the free state. The ester which was obtained, after being deprived of free acid, was separated into phenolic and non-phenolic portions by means of aqueous sodium hydroxide. The non-phenolic ester, which had the odour of methyl benzoate, yielded, on hydrolysis, a small amount of an acid, which crystallised from water in colour¬ less leaflets, melting at 121°, and was identified as benzoic acid. The phenolic ester, when hydrolysed, gave a mixture of acids which was found to be similar to the portion of the original acid mixture which had resisted esterification. The total quantity was therefore fractionally crystallised many times from a mixture of chloroform and benzene, when it was eventually separated into two compounds, melting at 155° and 135° respectively. The former of these products, which was the smaller in amount, proved to be salicylic acid. (Found, C = 607; H=4 5. Calc., C = 609; II =44 percent.)