The identification of ipuranol and some allied compounds as phytosterol glucosides / by Frederick B. Power and Arthur H. Salway.

  • Frederick Belding Power
Date:
1913
Catalogue details

Licence: In copyright

Credit: The identification of ipuranol and some allied compounds as phytosterol glucosides / by Frederick B. Power and Arthur H. Salway. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    (T., 1909, 95, 1988) and from the bark of Erythrophloeum Guineensc (Amer. J. Pharm., 1912, 84, 348), but not in amounts sufficient for analysis. Name ami formula. Ipnrauol, C23H40O4 II II II II II II II II II II II II II II II II II Citrullol, II I I I » II II II II II I* II • 1 022^38^4 Trifolianol, C21H30O4 11 i> Calaliarol, C931138O4 Ipurganol, C21H34O4 Bryi.nol, C22H3(j04 Grindelol, C23H3aC>4 Ationol, 023113304 Cucurliitol, C24II40O4 Cluytlano], C29Hj50O5 II II Source. M.p. and analj sis. acetyl derivative. C. H. C. B. Ipomoea purpurea 285 - 290”. 72 6; 10-6 160”. Olive bark 285-290”. 72-6; 10 8 160”. 69*8 ; 94 Nutmeg — 163-164”. 69-5 ; 9*4 Prunus terotina, bark 285-290”. 72 3 ; 10-7 160”. „ „ leaves 295. 163”. Apoeynum andro*aemifolium 285—290”. 72-4; 10-5 162”. J(itm-x Ecklonianus 2*5—290”. 162”. Ornithogalum thyrtoid.es .... 285-29””. 72-3 ; 10-5 162”. Q-elsemium sempervirmt .. 290”. 72-3; 105 162”. Ins versicolor 285-290”. 72 3; 10 3 162—103”. Withania somnifeta 285—-, 90”. 72 4; 10-3 164—165”. Buphane disticha 286”. Oenanthe crocata 285—290”. 161”. Casimiroa edulis 280—2*5”. 72-0 ; 10-4 166”. 69-7 ; 9-5 Ipomoea orizabensit 285—290”. 72-4; 10-6 162”. Scnmmony root 285—290”. 72-2; 10-6 162*. Colocynth 285—290”. 72-0; 10-6 167”. 69-3; 9-2 Eunvymus alropurpurcu*.. .. 285—290”. 71-9; 10-7 164—165”. t9*0; 9-3 Caulophyllum ihaliclroides.. 275—280”. 71-9; 104 109—170”. Trifolium pratense 295”. 71-4; 10-4 165—166”. 68-8; 9-2 ,, incaruatum Calabar bean 295—300°. 71-6; 10-4 165—ICO”. 68-6; 9-2 245”. 73-1 ; 10-1 — 1 Ipomoea purga 222—225”. 71-7; 10-0 166—167”. 68-9; 8-8 Bryony root 210—212”. 72-3; 10-1 153”. 691; 9-0 Orindelia camporum 257”. 72-7; 10-2 161”. — Anona muricata 294—293”. 72-9; 10-3 166”. — W .termelon seed 260”. 73-2; 104 150”. — Cluytia similis 300—305”. 72-8 ; 10-5 160”. 68-7 ; 9-1 Taraxacum root 297”. 72-5; 10-6 161*. 68-6; 9-1 In a few instances benzoyl derivatives of the above-mentioned compounds were prepared, which had the following characters: Benzoylipuranol, from Oenanthe crocata and Casimiroa edulis, melting at 196° and 197° respectively; benzoylanonol, m. p. 197—198°. C = 75'9; H = 7'8; benzoylcalabarol, m. p. 195—196°. G'=76T; H = 7”8; benzoylcluytianol (from Cluytia similis), m. p. 192°. C = 76'3; H = 7”7; (from taraxacum root), m. p. 196°. C = 76-2; H = 7'9 per cent. It is well known that a considerable number of isomeric phyto- sterols occur in nature which possess the formula C27H460, whilst other compounds of this type are represented by the formula C30H50O (or C30H48O) and C^H^O. As examples of these different classes there may be noted: sitosterol, C27H460 (Monatsh., 1897, 18, 551), stigmasterol, C30H60O or C30H48O (Ber., 1906, 39, 4378), and rhamnol, C^H^O (Proc. Amer. Pharm. Assoc., 1904, 52, 299). The glucosides and their acetyl and benzoyl derivatives of the first two types of phytosterols mentioned would have the following composition respectively: Sitosterol Glucoside and Derivatives. G'33H5flO0 requires C = 72‘3; H = 10'2 per cent. C33H5oO0(CO-CH3)4 requires C = 68‘7; H = 8'9 per cent. C33H5206(C0-C6H6)4 „ C = 75 9; H = 7”5 >1 »