Commercial notes and scientific information. 99 



when phosphorus is allowed to act upon pinene under access of air, an absorption of 

 oxygen by the pinene-molecule under formation of pinol actually does occur. Pinol may 

 not be formed until decomposition has set in. Moreover, it is questionable whether the 

 notation given above correctly represents the molecular structure, because the chaining 

 of the pinol molecule with the radical of the acid by means of a double bond is not very 

 probable, altogether apart from the fact that, if this did occur, the molecule would acquire 



/OH /OH 



the formula P=0 . Perhaps a more correct formula would be: O^P H 



^C 10 H 14 O ^CioH,*0 



Eventually the formula of a molecular modification Ci Hi 9 PO 3 orCi H 1(J O, H ;i PO, 

 must be taken into account, as the analytical values ascertained by Sieburg may also 

 apply to this. 



In experiments in the synthesis of turpentine-phosphorous acid the author heated 

 both newly-distilled and oxidised pinene with phosphorous- and with hypophosphorous 

 acid in a reflux condenser, as well as with phosphorus trichloride, adding aluminium 

 chloride, but with negative results. Nor did the desired reaction occur when hydration- 

 products of pinene, such as terpineol and terpin hydrate were heated with phosphorus. 

 Sieburg has not carried out these reactions with pinol. 



Experiments with chickens, rabbits, and dogs showed not only that pinol hypo- 

 phosphorous acid has ceased to have any effect of phosphorus, but also that it is 

 completely non-toxic. It is eliminated in the urine of the experimental animal in the 

 form of pinol phosphorous acid. No formation of combined or free glucuronic acid in 

 the animal organism was observed. The antibacterial properties of the body are 

 negligible. 



In conclusion we reproduce verbatim Sieburg's summary of the results of his 

 investigations. 



1. From turpentine oil (pinene) and phosphorus a compound is formed extra 

 corpus. This body should not be designated as turpentine-phosphorous acid. 



2. Terpenol-hypophosphorous acid is a better name for it. 



3. Those salts of the body which have been analysed, viz., the Na-, Li-, Ba-, and 

 Pb-salt, indicate an unibasic acid. 



4. When gently oxidised in a test-tube it gives rise to terpenol-phosphorous acid. 



5. The non-toxic terpenol-hypophosphorous acid undergoes a similar, albeit not 

 identical, conversion in the animal organism, as it does when gently oxidised 

 in a test-tube, that is to say, it is eliminated in the form of terpenol-phos- 

 phorous acid P(OH) 2 OC 10 H 17 O. 



6. This behaviour at the same time supports the assertion that the product of 

 reaction of phosphorus upon terpene is a chemical compound of this character; 

 also, that in the said substance the phosphorus is intimately attached to the 

 hydrocarbon, as otherwise according to all experience the last-named would 

 be eliminated from the organism in the form of a glucurone-combination. 



The question, extremely important from a medical point of view, whether the 

 formation of a non-toxic body as a result of the action of terpenes upon phosphorus 

 in the presence of oxygen is capable of being practically utilised in cases of phos- 

 phorus-poisoning, is to be treated by the author in a subsequent paper. 



In connection with the above we desire to make known the experiments in the 

 preparation and purification of so-called turpentine-phosphorous acid, which were carried 

 out by us as long ago as the years 1903 and 1904. The experiments were not con- 



