78 BACON. 



THE COMPOSITION OF YLANG-YLAN'G OIL. 



The cliemieal composilion of ylang-ylang oil lias been pretty well 

 established through tlie labors of many chemists. 



Gal ° foiuid no aldeliydes or ketones, but benzoic acid as esters of unlinown 

 alcohols. Fliickiger/ correctly names the tree from whicli jdang-ylang oil is 

 obtained and gives a good historical rgsumfi concerning the oil and its introduction 

 into Europe. He found in the oil a very small amount of benzoic acid, acetic acid 

 and unidentified phenols (from the color reactions with ferric chloride) and 

 suspected the presence of an aldehj'de or ketone. 



He obtained a very small amount of a precipitate with sodium bisulphite. He 

 was unable to identify any of the alcohols from the oil. There would seem to 

 be some doubt as to whether Fliickiger studied a genuine sample of ylang-ylang 

 oil, as the esters of benzoic acid are so abundantly present that the acid is 

 separated in quantity Avith the greatest of ease. Eeychler ' found benzoic and 

 acetic acids, linalool, geraniol and cadinene. Darzens " found methyl alcohol, 

 pora-kresol, benzoic and acetic acids and considered that the paro-kresol was 

 present as the acetate, for he states that para-kresol acetate has an odor 

 somewhat like that of ylang-ylang oil. The final and most exhaustive researches 

 on this perfume oil are due to the commercial houses, especially to Schimmel & 

 Company," whose results are embodied in a patent for artificial ylang-ylang oil. 



A rational method of analysis of this oil should, if possible, be founded 

 on its composition, and therefore we have undertaken studies in this 

 direction and have succeeded in adding two new substances, formic acid 

 and safrol (isosafrol), to the list of the known constituents of the ylang- 

 ylang oil. 



Experiment 1. — One hundred grams of first-grade ylang-ylang oil were taken: 

 its constants were as follows: Specific gra's'ity, — ^:=0.921; A-=— = — 40.7; 



N^^^ = 1.4825; ester number, 108. 



This oil gave only a very faint reaction with ferric chloride at the contact 

 zone, due to methyl salicylate, showing that the phenols were combined. It is 

 interesting to note that none of the oils I have handled gave a strong color reaction 

 with ferric chloride, and therefore the possibility suggests itself that the ageing 

 of the oil causes a small amount of hyurol3'sis of the phenol-ethers, for most 

 European observers have obtained pronounced color reactions with ferric chloride. 



N 

 The oil I used was more than neutralized with 0.1 cubic centimeter of caustic 



10 

 soda. All good ylang-ylang oils are neutral. 



Tlie oil was heated to 100° in a sealed tube with 15 giams of sodium hydroxide, 

 dissolved in 30 cubic centimeters of water, for eiglit hours. At the end of this 

 time a considerable amount of solid has separated; there was no pressure in the 

 tube. The contents ■\\'as dissolved in water and ether, the etlierial layer separated, 



^Compt. rend. Acad. d. sc, Par. (1873), 76, 1482. 

 'Arch. d. Pharrri: (1885), 18, 24. 

 \Biai. Soc. Ghim. Paris (1894), 11, 407, 540, 1057. 

 'Ibid. (1897), 27, S3. 



'" D. R. P. 142, 859 Class 23, a. Schimmel & Company, semiannual report, 

 October 1901 (English edition), p. 53. 



