48 Report of Schimmel § Co. 1922. 



fractions solidify to a crystalline mass—, and 10 g. of a viscous oil, b. p. 170 to 185°. 

 Repeated crystallisation of the solid fractions yielded a body Ci 5 H 26 0, machilol; 

 m. p. 79 to 80°, b. p. 160° (14 mm.), [a] D25 o + 42.87°. On treatment with acetic anhydride 

 and sodium acetate the body is acetylated but partly; neither is formed a phenylurethane 

 with phenyKsocyonate nor a benzoate according to Schotten-Baumann. Reduction with 

 platinum black and hydrogen yielded dihydromachilol Ci 5 H 28 0, m. p. 82 to 83°, b. p. 157 

 to 158 (14 mm.), [«] D18 o + 16.43°. By oxidation with potassium permanganate, machilol 

 passed over into dihydroxymachilol, or machilene glycerol Ci5H 28 0(OH2 + H 2 0, m.p. 110°, 

 [«]di30 — 25.91°; monobenzoate, m.p. 142°. This body proved to be identical with 

 a-dihydroxyatractylol which the auther obtained, in addition to /?-dihydroxyatractylol 

 (m.p. about 78°, [«] D13 o + 24.68°), on oxidising atractylol by the same reagent. Hence, 

 machilol is a bicyclic, tertiary sesquiterpene alcohol. 



When machilol was heated with formic acid, machilene Ci 5 H 24 resulted; b. p. 120° 

 (3 mm.), df^ 0.9109, [«] D23 o + 58.73°, n D23 o 1.51257; Liebermann's reaction: first blue, then 

 green, and after some standing dark blue. On reducing machilene with hydrogen and 

 platinum in glacial acetic acid, tetrahydromachilene Ci 5 H 28 was formed; b. p. 132° 

 (11mm.), dg 0.8964, [«] D10O + 37.04°, n D10O 1.48645. 



Machilene is no uniform body, but a mixture of probably two isomerides, for on 

 abstracting water from machilol by weaker-acting reagents, an isomeride of machilene 

 is formed with higher rotatory power (« D about +100°). 



On reducing atractylene (b. p. 108 to 109° [3 mm.], d^ 0.9189, [«] D13 o + 78.35°, 

 n D130 1.51795) catalytically, tetrahydroatractylene is formed (b. p. 129 to 130° [10 mm.], 

 d^ 0.9030, [«] D120 + 36.99°, n D12Q 1.49589), a liquid with a feeble but pleasant odour. 



Since the. tetrahydro derivatives of machilol and atractylol agree very closely in 

 their qualities, Takagi ascribes to atractylol (or atractylene) and to machilol (or machilene) 

 the same carbon nucleus, both bodies differing merely by the position of the double 

 linking and the hydroxyl group. 



Massoi Bark Oil. — According to the Imperial Institute 1 ), the Massoi bark from the 

 Fiji Islands and New Guinea and sold on the Singapore market, comes from Cinnamomum 

 pedatinervium, Meissn. (identical with Massoia aromatica, Beccari [?]) 2 ). 



Milfoil Oil. — An extensive publication on this oil has been published by 

 R. E. Kremers 3 ). The crude material, Achillea Millefolium, L. serving for the investigation 

 was collected from the middle of June to the middle of July, freed carefully from foreign 

 matter, and dried immediately at the open air. About 1200 pounds of fresh herb weighed 

 after three days' drying 42072 pounds or 190.7 kilos, and yielded 892 g. of oil, or 

 0.467 per cent, of the dry herb. This exceptionally high 4 ) yield of essential oil was 

 arrived at by cohobating the distillation-water, thus obtaining in addition to the principal 

 oil, 21 per cent, of "water oil", calculated on the former oil. 



Firstly, the "water oil" was subjected to fractional distillation. The fractions, 

 b. p. between 64 and 90°, proved to contain formaldehyde (by its odour, and Schiffs 

 reagent), methyl alcohol (methyl salicylate, formaldehyde, and 3, 5-dinitrobenzoic methyl 

 ester), ethyl alcohol (iodoform reaction), acetone (reaction with sodium nitroprusside 

 and iodine potassium iodide), furfural (aniline acetate), borneol (m. p. 203 to 204°). 



r ) Bull. Imp. Inst. 19 (192*1), 338. — 2 ) As to the still doubtful origin of the Massoi bark of commerce 

 see Gildemeister and Hoffmann, The Volatile Oils, 2 nd edition, vol. II, p. 498. — 3 ) Journ. Americ. pharm. Assoc. 

 10 (1921), 352. — 4 ) From dried blossoms once even 0.485 per cent, oil were obtained, from fresh blossoms, 

 as a rule, 0.07 to 0.25 per cent. Cf. Gildemeister and Hoffmann, The Volatile Oils, 2 nd ed., vol. Ill, p. 617. 



