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134% sles ee “Report OF SCHINMEL & Ce “APRIL a Oct BE 
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likewise bocaknes insoluble in chloroform. The light - oly sr ed ) 
cinnamates remain soluble in cold chloroform, even after having been 
long-time up to 140°. 
Constitution of anemonin. On page 80 of our April Report 1915, we hae Tee 
a treatise by Y. Asahina on anemonin (I), the volatile component of some anemones. 
The author thinks to have proved the presence of two double linkings in the molecule 
of this interesting body. In the meantime, he has issued another publication on the- 
constitution of anemonin‘*), in which is shown that it must-be considered as a lactone. 
On heating it with alkali on a water-bath, an alkaline solution is obtained, provided - 
the quantity of alkali exceeds what is necessary in order to neutralize two carboxyl 
groups. Ammoniacal solution of silver and Fehling’s solution are reduced by anemonin 
in the heat. It forms a condensation product with phenylhydrazin, which indicates 
the presence of a carboxyl group. No semicarbazone or oxime could be obtained. 
Asahina identified the acetonediacetic acid (II) (hydrochelidonic acid) as an oxidation 
product of the potash salt of afiemonic acid. He looks upon anemonin as a dilactone 
of a cyclooctanonedienedicarboxylic acid. On saponification of the lactone group, two 
keto acids, anemonic and anemoninic acids (Ill), are obtained. 
The results of later investigations of the anemonin have been published by Asahina*) 
elsewhere. He repeated Beckurts’*) bromination experiments and was able to confirm 
his indications, with the exception that he found the m. p. of tetrabromoanemonin at 
-C 
4 H.:CH2:-C-CO.H 
SOY CH, 2 | O2 
O . // ile: CHa CO2H | | 
3 C CO CO C-OH 
Ow | \CH)- CH: CO.H | 
CO_ (11) Acetonediacetic acid. 
H,C—— CH, CH, -CH, } CH: CO.H 
(I) Anemonin. (III) Anemoninic acid. 
175°, whereas Beckurts mentions 205°. It is remarkable that anemonin absorbs the 
bromine rather sluggishly. Not only with bromine, but also with hydrogen halogenides, 
anemonin behaves like a doubly unsaturated body, fopming with hydrobromic acid a 
beautifully crystallizing dihydrobromide, m. p. 182°. 
The so-called anemoninic acid (III), which forms on hydrolysis of anemonin with 
absorption of two molecules of water, had been obtained before only in the amorphous 
state and analyzed as salt. Asahina has now prepared it in the form of white, needle- 
shaped crystals, m. p. 116 to 117°. Beckurts indicates the same m. p. for the amorphous 
product. Asahina does not share Beckurts’ view that the anemoninic acid is a hydrate 
of the anemonic acid, but thinks that relation far more complicated. The colour reaction 
with alkali, not shown by anemonic acid, is a characteristic of anemoninic acid. 
If anemonin is heated with an exactly equivalent quantity of alkali hydroxide solution, 
a passing reddish-brown coloration is noticed, which disappears quickly as soon as 
the hydrolysis is completed, leaving the solution pale yellow. The neutral alkali ane- 
moninate is but slightly yellow, the reddish-brown colour reappears, however, on 
addition of a few drops of alkali. This behaviour may best be explained by the 
1) On the constitution of anemonin. Yakugakuzasshi, 1915, February number, page 1; Journ de Pharm. 
et Chim.- VII. 12 (1915), 293. — 2%) Arch. der Pharm, 258 (1915), 590. — *) 1bidem 280 (1892), 205. 
