,9 ~ » - 



F. W. Semmler, in conjunction with E. W. Mayer 1 ), has continued his 

 researches in cedarwood oil, and has discovered a new constituent in the 

 form of a primary sesquiterpene alcohol, to which he has given the name 

 of cedrenol. This body occurs in those fractions of the oil which boil 

 between 152 and 170° (7 mm.) (« D20 o + 17,5°) and can be isolated there- 

 from by warming with phthalic anhydride in benzene solution. The alcohol, 

 when purified from primarily-produced acetate, possesses the following 

 properties: b. p. 166 to 169° (9,5 mm.), d 20 o 1,0083, « D20 o±0°, n D20O 1,5212. 

 The acetate occurs in the form of a colourless liquid, b. p. 165 to 169° 

 (9,5 mm.): d 20 o 1,0168, « D — 2°, n D20 o 1,5021. Cedrenyl chloride boils bet- 

 ween 150 and 165° (10 mm.): d 20 o 1,001. When heated with sodium and 

 alcohol the chloride yields an ethylether and a hydrocarbon which proved 

 to be identical with cedrene, as was shown by oxidation into cedrene 

 keto-acid and into cedrene dicarboxylic acid 2 ). 



Cedrenol stands in the same relation towards cedrene as do the two 

 primary alcohols of the santalol series towards the sesquiterpenes C15H24, 

 the santalenes; and as myrtenol and the gingergrass alcohol stand towards 

 pinene and limonene 3 ). The primary CH 2 OH-group in the cedrenol molecule 

 occupies the same position which is occupied by the CH 3 -group in cedrene 

 and in solid cedrol. Hence the relation of cedrene towards cedrol and 

 cedrenol is as follows: — 



(C13H20) 



i\ 



C:CH 



(C13H20) 



C(OH)CH 2 



(C i3 H 2 o) 



!\ 



C:CH 



CH 3 



CH 3 



CH 2 OH 



Cedrene, C15H24. 



Cedrol, Ci 5 H 26 0. 



Cedrenol, C15H24O. 



In addition to cedrenol, Semmler and Mayer 4 ) have observed in cedar 

 oil a saturated alcohol; pseudo-cedrol (Ci 5 H 2 6 0). This alcohol was found 

 to occur in the fractions boiling between 145 and 155° (10 mm.), from 

 which the cedrenol was removed by heating with phthalic anhydride. It 

 boils between 147 and 152° and constitutes a viscous oil with the following 

 constants: d^o 0,9964, « D20O -(-21,5°, n D20 o 1,5131. Its tertiary character is 

 evident from the fact that when heated with zinc dust in a sealed tube 

 to 225 to 235° its oxygen was abstracted from it, and the corresponding 

 Saturated hydrocarbon, dihydrocedrene, was formed, the latter, in this case, 

 being contaminated with about 50 p. c. cedrene. In order to obtain dihydro- 

 cedrene in the pure state, ozone was introduced into the hydrocarbon- 

 mixture in a chloroform-solution until bromine ceased to lose its colour. 

 Dihydrocedrene boils between 109 and 112° (10 mm.): d 20 o 0,907, « D + 37°, 



!) Berl. Berichte 45 (1912), 786. 

 2 ) Comp. Report April 1912, 173. 

 z ) Comp. Report April 1911, 76. 

 J ) Berl. Berichte 45 (1912), 1384. 



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