
%0 Journal Article
%A Lamberton, JA 
%T Studies of the optically active compounds of Anacardiaceae exudates. V. Further investigation of the exudate from <I>Campnosperma auriculata</I> Hook. F
%J Australian Journal of Chemistry
%D 1959/06/01
%V 12
%N 2
%P 224-233
%K 
%R https://doi.org/10.1071/CH9590224
%U https://www.publish.csiro.au/paper/CH9590224 
%X Distillation of the hydrogenated oil from Campnosperma auriculata Hook. f. yields n-pentacosane-2,6-dione (IV), which is formed from (+)-3-hydroxy-3-nonadecylcyclohexanone (II) by a retro-aldol reaction. In alcoholic alkali, IV is recyclized to 3-nona-decylcyclohex-2-enone (III), and on Wolff-Kishner reduction the disemicarbazone of IV yields n-pentacosane. Oxidation of 3-nonadecylcyclohex-2-enone (III) yields 5-ketotetracosanoic acid, which has been synthesized by an improved method. The synthesis of III and of 3-heptadecylcyclohex-2-enone is described and a convenient method is given for the preparation of 3-methylcyclohex-2-enone.   Examination of the mixture of phenols obtained by the action of alkali on C. auriculata oil has shown the presence of 3-nonadecyl phenol and a mixture composed predominantly of cis-monoethylenic C,, alkyl phenols. The phenols are admixed with a small amount of certain long-chain quinols which are also present in the original oils. Nonadecylquinol, one component, has been characterized by conversion into nonadecyl-benzoquinone.   The exudate from Campnosperma macrophylla Hook. f. (also Malayan) is unlike that from C. auriculata and contains little oil. 
