Commercial notes and scientific information. 



109 



a,«'-methyk'sopropyl-«,«'-dihydroxyadipic acid. As a matter of fact, when oxidised with 

 permanganate of potassium in alkaline solution it yielded an acid melting at 190 to 

 191° which, when heated to 210° was converted into its anhydride and, when further 

 heated to 250°, afforded the anhydride of ascaridolic acid. It is to be expected that the 

 four possible optically active modifications of a-«'-methyl?'.s-opropyl-«, «-dihydroxyadipic 

 acid are capable of forming two dilactones and two acid anhydrides. The fact that 

 the acid with m. p. 190 to 191° is a substituted adipic acid, is evident from its behaviour 

 under oxidation with potassium permanganate in acid solution. When subjected to 

 this reaction it forms a ketone of which the semicarbazone melts between 201 and 

 202° and gives the pyrrol reaction when heated in a test-tube. The behaviour of the 

 semicarbazone agrees with that of the semicarbazone of 2-methylheptane-3,6-dione, 

 the oxidation-product of «,«'-methyKsopropyl-«,« f -dihydroxyadipic add. 



By means of permanganate of potassium in acid solution Nelson has resolved 

 the acid Ci H 16 O 5 , the oxidation-product of «-glycol from ascaridole, into 2-methyl- 

 heptane-3,6-dione (semicarbazone, m. p. 201 to 202°; oxime, m. p. 130 to 131°). 

 Energetic oxidation of «-glycol also affords 2-methylheptane-3,6-dione. 



In order to explain the rise of the «-glycol from ascaridole, Nelson assumes the 

 transposition-product (II) to be a labile dioxide which is converted into «-glycol (V) 

 by way of the stable modification (IV). In that case the acid obtained from «-glycol 

 must be 1,4-cineolic acid (VI). 



By reacting with saturated oxalic acid solution upon the anhydride of «-glycol 

 there was obtained the same phenol-like body which had resulted from «- and /^-glycol 

 by heating with dilute sulphuric acid. It is an isomeride of diosphenol, but it does 

 not reduce either Fehling's solution or ammoniacal silver-solution. When the «-glycol 

 anhydride is heated with benzoic acid it yields, in lieu of the expected benzoate, 

 benzoylcarvacrol (carvacrol phenylurethane, m. p. 140°). 



C-CH 8 



C-CHo 



CH 



' I'CH 



H 2 C 

 H 2 C 



C-C 3 H 7 



(I) Ascaridole (Wallach). 



H 2 C 

 H 2 C 



CH 



CH 



C 3 H 7 



(II) Conversion product. 



C-CH„ 



H 2 C 

 H 2 C 



CH 



o I > O 



CH 



H 2 C, 

 H 2 C 



CHOH 



C-CsH, 



(IV) Hypothetical stable Dihydroxide. 



C'-CaH, 

 (V) et-Glycol. 



H 2 C 



C-CH 3 

 /J^CHOH 



H 2 C 



vf^JCHOH 



C'C 3 H, 



(III) Erythritol. 



H 2 C 



CCH 3 



/ I^COOH 

 o 



H 2 C 



v | yCOOH 



C-C 3 H T 



(VI) 1, 



4-Cineolic acid. 



Oil of Levant Wormseed. We have already stated that for some considerable time 

 it has been impossible to procure this oil (Oleum cince). It w r ould appear that consumers 

 are resigned to this fact, for we only very rarely receive enquiries for the article. 



Wormseed oil is now hardly to be found in commerce, the reason being probably 

 that the parent-plant (Artemisia maritima, L. var. Stechmanni = A.Cina, Berg, N.O. Com- 

 positce), is not now distilled as it used to be, prior to being worked up for santonin. 



