3 86 



gravity at 15 C. = 0-9471 ; rotation a D - - 98-4, and refractive index at 20 

 = i '4864. It was then distilled under reduced pressure, when 90 per cent, came 

 over at 101-102 C. at 10 millimetres. It had the following constants : 



Specific gravity at 20 C 0-94165. 



Optical rotation a D ... ... ... ... ... - - 98-24. 



Refractive index at 20 C. = 1-4858. 



Oxime melted at 84-85 C. 



Hydrazone melted at 119-120 C. 



Semicarbazone melted at ... ... ... ... ... 173 C. 



(Both the oxime and hydrazone were produced by the highly rotatory 

 aldehyde allied to phellandral, because those formed with cryptal are liquid.) 



The aldehyde thus prepared was then shaken with a 35 per cent, 

 solution of neutral sodium sulphite at room temperature (20 C.), repeatedly 

 neutralising the separated sodium hydrate with standard acid, until combination 

 was complete. The uncombined aldehyde was then removed by ether, dried and 

 weighed. 



Amount of original aldehyde taken ... ... = 15-9822 gram. 



uncombined ... = 5-9074 



,, ,, combined ... ... 10-0748 ,, 



This result was very satisfactory for an aldehyde with the C IO H I6 O molecule. 

 The combined aldehyde was regenerated from the aqueous solution by sodium 

 hydrate, extracted with ether and prepared in the usual way. The constants, 

 with varying degrees in optical rotation with the different species, are those for 

 cryptal. 



Specific gravity at 20 C. ... ... ... ... ; 0-9431. 



Optical rotation D ... ... ... ... ... - - 76-02. 



Refractive index at 20 C. ... ... ... ... = 1-4830. 



Boiling point at 10 millimetres ... ... ... 98-100 C. 



7 6 .- 221 C. 



Semicarbazone melted at ... ... ... ... 176-177 C. 



The oxime and hydrazone were both liquid, and so far we have not succeeded 

 in forming these in a satisfactory crystallised condition. 



The aldehyde which did not combine with neutral sodium sulphite in the 

 cold, and was not decomposed by sodium carbonate, had a remarkably high 

 rotation. It gave the following constants : 



Specific gravity at 20 C. ... ... ... ... = 0-9408. 



Optical rotation a D ... ... ... ... ... - - 130-6 C. 



Refractive index at 20 C. ... ... ... ... 1-4901. 



Boiling point at 10 millimetres ... ... ... 102-103 C. 



Oxime melted at 87-88 C. 



Hydrazone melted at ... ... ... ... 119-120 C. 



Semicarbazone melted at ... ... ... ... 204-205 C. 



When oxidised by means of air, the acid melted at 137-138 C. 



These figures closely agree with those given for phellandral ; the aldehyde 

 had evidently the C IO H I6 O molecule with one double linkage. 



On the completion of the above work it was decided to procure fresh material 

 of E. hemiphloia, for purposes of comparison. As the date of collection was less 

 than four weeks from the above, but little differences were observed from those 

 already given, except that the cuminal fraction was but 11-8. The same mode 

 of procedure was adopted throughout as in the previous case. The aldehyde 



