Chemical Preparations and Drugs. 63 



and Herissey in Asperula odorata and in Melilotus species). According to O. von Lipp- 

 mann 1 ) a glucoside containing coumarin occurs also in a variety of Melilotus arvensis- 

 which grows in Central Germany on railway embankments. The glucoside itself has 

 so far not been isolated, but the coumarin was obtained and characterised after treat- 

 ment of the expressed juice with emulsin. 



As regards the solubility of coumarin in water and glycerin, see page 95 of this Report 



As regards an adulteration of coumarin with magnesium sulphate, cf . p. 76 of this Report. 



Eucalyptole. — Some years ago ). Belluci and L. Grassi 2 ) investigated a number of 

 different compounds which cineole forms particularly with phenol bodies, such as «- 

 and /2-naphthol, o-, m- and jo-cresol, pyrocatechol, thymol $c. Recently T. Tusting 

 Cocking 3 ) has prepared the addition-product of cineole and o-cresol again in a pure 

 condition, and has further investigated it. This compound which he calls cresineol 

 is at once deposited in crystals when cineole acid o-cresol are mixed in molecular 

 proportions. It has the following properties: — m. p. 55.2°; d^|0.%61; n D60 o 1.4846; 

 soluble in ether, alcohol and in all organic solvents. 



Starting from this investigation the author has worked out the following method for 

 the quantitative estimation of the cineole contents in eucalyptus oil by a cryoscopic 

 test, making use of cresineol: — 3 g. of eucalyptus oil are mixed with 2.1 g. of o-cresol. 

 From the solidification point of this mixture the required value is deduced by means 

 of a graphic table and found, it is said, correct within + 3 per cent., provided that the 

 portion of the oil, which does not contain cineole, consists only of terpenes and sesqui- 

 terpenes. The error will be the smaller, the greater the contents of cineole, but it may 

 rise up to 6 per cent, in the presence of alcohols and esters. Cocking obtains his 

 tables by systematically determining the solidification points, on the one hand, of 

 numerous mixtures of cineole and terebene, and, on the other hand, of mixtures of 

 cineole and sesquiterpene (copaiba oil). Graphically represented the points obtained 

 give two curves, the maximum difference between which will correspond to a cineole 

 contents of 6 per cent. In the intermediate curve of the author the error limit would 

 be reduced to three per cent. 



In a later communication Cocking 4 ) refutes the objections which Bennett and 

 Salamon had raised against the cresineol method in favour of their phosphoric-acid 

 method. The author emphasizes that only the presence of large amounts (33 per cent.) 

 of foreign ketones, terpene alcohols and, above all, of esters could increase the errors 

 of his method to 6.3 per cent, whilst the phosphoric-acid method would, for various 

 reasons which he discusses in detail, give results, too low by 13 percent, maximum. 

 These statements confirm our own experience with the phosphoric-acid method, to the 

 uselessness and unreliability of which we have frequently drawn attention 5 ). 



In a further communication on the eucalyptole determination Bennett and Salamon ) 

 confirm on the strength of their own experiments that Cooking's cresol method admits 

 of an approximate, rapid and easy estimation of the cineole in eucalyptus oil, provided 

 that more than 45 per cent, of cineole be present in the oil. The freezing-point method 

 of Kleber and W. v. Rechenberg 7 ) seems, according to the experiments of these authors, 

 to give uniform results; but they find it only convenient when the eucalyptole contents 

 amounted to more than 70 per cent. 



!) Berl. Berichte 53 (1920), 2072. — 2 ) Cf. Report April 1914, 147. — 3 ) Perf. Record 11 (1920), 281. 

 — *) Perf am. Record 11 (1920), 363. — 5 ) Cf. Report October 1907, 47; October 1915, 17; 1920, 34. — 

 8 ) Perfam. Revjrd 12 (1921), 11. — <) See p. 23 of this Report. 



