ON KHELLACTONE

E. Späth; W. Gruber; O. Matzke

doi:10.1139/v53-097

ON KHELLACTONE

Canadian Journal of Chemistry ◽

10.1139/v53-097 ◽

1953 ◽

Vol 31 (8) ◽

pp. 715-721 ◽

Cited By ~ 4

Author(s):

E. Späth ◽

W. Gruber ◽

O. Matzke

Keyword(s):

Potassium Hydroxide ◽

Optically Active ◽

Minor Constituent ◽

Alcoholic Alkali ◽

Active Compounds ◽

Dehydration Product ◽

Alcoholic Potassium Hydroxide ◽

Hydroxyisobutyric Acid

A hitherto unknown minor constituent of the seeds of Ammivisnaga Lam is converted under the influence of 5% alcoholic potassium hydroxide into a compound which seems to be a coumarin. Treatment with methyl-alcoholic alkali yields a substance C15H16O5, whereas treatment with ethyl-alcoholic alkali gives a substance C16H18O5. Dehydrating agents convert both optically active compounds into the same optically inactive dehydration product C14Hl2O4 (Substance A). The further investigations carried out with Substance A were: oxidation, after methylation, which yielded α-hydroxyisobutyric acid; fusion with potassium hydroxide, which gave phloroglucinol. On treatment with diluted caustic alkalies two definite products, C10H6O5, probably an acid, and C11H8O4, a ketone, were obtained.

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Studies of the optically active compounds of Anacardiaceae exudates. V. Further investigation of the exudate from Campnosperma auriculata Hook. F

Australian Journal of Chemistry ◽

10.1071/ch9590224 ◽

1959 ◽

Vol 12 (2) ◽

pp. 224 ◽

Cited By ~ 8

Author(s):

JA Lamberton

Keyword(s):

Convenient Method ◽

Aldol Reaction ◽

Optically Active ◽

Improved Method ◽

Alcoholic Alkali ◽

Active Compounds ◽

Hydrogenated Oil ◽

Alkyl Phenols ◽

Long Chain

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.

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