Notes on scientific research. 77 



with more and with 4 vol. turbidity; acid v. 0.3 and 2.22; ester v. 42.31 and 31.82 

 (corresponding to 14.81 per cent, and 11.13 per cent, of linalyl acetate); ester v. after 

 acetyl. 131.12 and 117.0 (corresponding to a total alcohol percentage of 37.75 and 33.78 

 and a free alcohol percentage of 25.84 and 25.02). The alcoholic solutions of the oils 

 were fluorescent. 



A Sweet Orange Blossom Oil from Sevilla ("Portugal extra") gave the following 

 properties: — di 5 o 0.8554; « D150 + 41° 36'; n D15 o 1.7444; soluble in 8 vol. 90 per cent, 

 alcohol; acid v. 3.43; ester v. 15.10, 5.29 per cent, of linalylacetate; ester v. after 

 acetyl. 76.48; total alcohol 23.33 per cent., free alco v hol 16.48 per cent. 



The following Rue Oils came partly from Ruta montana, L. (the oil from Malaga, 

 certainly, the oils from Cordoba and Sevilla most likely), partly from Ruta bracteosa. L.. or 

 Ruta graveolens, L. (the oil from Carcagente). 



Spanish Eue Oils. Carcagente. Cordoba. Sevilla. Malaga. 



d 15 o . 0.8839 0.8329 0.8350 0.8364 



a 



D ; c 



0°24' +0°2' + 0°52' H-0°44' 



n 150 1.4320 1.4328 1.4333 1.4318 



!«..,. .. /-> I st ^f ing at + 3 °' starting at +8° to + 10° to 



Solidification point ... still incomplete ° ' ■ ... n 



I at -10°. +13° +10° 4-11° 



Solubility in alcohol of 



70 per cent 1 : 2.5 1 : 2.5 1 : 25 ? 1 : 2.5 



Acid v 4.4 1.8 2.25 1.3 



Ester v. ...... . 3.87 4.65 5.60 8.50 



ketones (hydroxylamine method) 

 calculated as 



methylheptylketone . . — — 81.1 per cent. 72 per cent, 



methylnonylketone . . — — 97.1 per cent. 86.4 per cent. 



Ester v. after acetyl. . . 24.04 10.86 18.02 — 



The oil from Cordoba gave in the Ladenburg flask at 710 mm. the following 

 fractions:— 195 to 210°, 7.58 per cent.; 210 to 215°, 16.60 per cent; 215 to 220°, 

 21.72 per cent.; 220 to 225°, 21.55 per cent; 225 to 230°, 23.13 per cent; 230 to 240°, 

 7.24 per cent; residue 2.18 per cent. The three first fractions (methylheptyl ketone and 

 methylnonyl ketone) did not solidify at 0°; the second and third fractions displayed 

 a strong bluish fluorescence (methylester of the methylanthranilic acid). The fourth 

 and fifth fractions solidified at -j-10° and +11° and did not fluoresce. From the 

 last fractions caprinic acid (m. p. 28 to 31°) was obtained by oxidation with sodium 

 hypobromite. 



Another rue oil from Cordoba, yielding 6 fractions between 210 and 242°, showed 

 no fluorescence and did not contain any methylheptyl ketone, but did contain methyl- 

 nonyl ketone. Consequently the Spanish rue oils might be traced back to 2 types, 

 the one of oils with a high solidification point, between 10 and 12°, not fluorescent, 

 and the other fluorescent and of a lower solidification point 



Of all the Geranium Oils the Spanish is the most highly esteemed on account of 

 its delicate odour. Of three authentic oils from Sevilla, Malaga and Valencia the first 

 seemed to be adulterated, being insoluble in 3 vol. 70 per cent, alcohol. The other two 

 oils had the following constants:— d 15 o 0.8828 and 0.9012; « D150 — 11°24' and — 9°10'; 

 noiso 1.4715 and 1.4730; soluble in 1.5 vol. 1 ) and in 1 vol. and more 80 percent alcohol, 

 soluble in 2.5 vol. 1 ) and in 2 vol. and more 70 per cent alcohol; acid v. 10.40 and 7.00; 



l ) On addition of 4 to 5 vol. of alcohol the mixture turned turbid and paraffin crystals appeared. 



