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

1959 ◽  
Vol 12 (2) ◽  
pp. 224 ◽  
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.

Studies of the optically active compounds of Anacardiaceae exudates. II. The action of Alkali on the long-chain alicyclic Keto Alcohol of Tigaso Oil

1958 ◽  
Vol 11 (1) ◽  
pp. 64 ◽  
Author(s):  
LK Dalton ◽  
JA Lamberton
Keyword(s):  
Optical Activity ◽  
Active Compound ◽  
Optical Rotation ◽  
Large Change ◽  
Optically Active ◽  
Bicyclic Compound ◽  
Compound I ◽  
Alcoholic Alkali ◽  
Rapid Reaction ◽  
Long Chain

In cold alcoholic alkali the optically active compound I from Tigaso oil undergoes a rapid reaction which involves loss of its conjugated carbonyl system, and a large change, with inversion, of its optical rotation. The reaction is interpreted as a cyclization and the product is provisionally formulated as a bicyclononane derivative IIa. In hot alcoholic alkali, IIa is not the final product ; the bicyclic compound undergoes further reaction to give a mixture in which the unsaturated monocyclic triketone VII (R=C16H31) appears to predominate, but which probably consists of a mixture of VII and VIII (R=C16H31). These can be hydrogenated to a mixture of saturated monocyclic triketones VII and VIII (R =C16H33). The same hydrogenated triketones are obtained if IIa is first hydrogenated and then heated with alcoholic alkali. These triketones are optically active and by oxidation with hypobromite, or with permanganate and then hypobromite, yield bromoform and the chemically homogeneous tribasic acid IX, which still retains optical activity. The isolation of the saturated hydroxydiketone IIb in 4 per cent, yield from hydrogenated Tigaso oil suggests that 11% is present to that extent in the original oil.

Studies of the optically active compounds of Anacardiaceae Exudates. IV. The structures of the rearrangement products from the long chain alicyclic ketoalocohol of Tigaso oil in Alkali

1958 ◽  
Vol 11 (4) ◽  
pp. 538
Author(s):  
JA Lamberton
Keyword(s):  
Methyl Ether ◽  
Active Compound ◽  
Monomethyl Ether ◽  
Optically Active ◽  
Side Chain ◽  
Lithium Aluminium Hydride ◽  
Active Compounds ◽  
Hydride Reduction ◽  
Lithium Aluminium ◽  
Long Chain

The structure IIIa previously proposed for the β-diketone with an unsaturated side chain, obtained by the action of alkali on the optically active compound of Tigaso oil, is confirmed by the formation of methyl stearyl ketone and resorcinol monomethyl ether in the pyrolysis of the methyl ether (IV). An anomalous lithium aluminium hydride reduction of the methyl ether (IV) and other reactions are discussed. Unsuccessful attempts have been made to synthesize the tribasic acid resulting from sodium hypobromite oxidation of the β-diketone (IIIb).

ON KHELLACTONE

1953 ◽  
Vol 31 (8) ◽  
pp. 715-721 ◽  
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.

Studies of the optically active compounds of Anacardiaceae exudates. III. The long-chain Alicyclic Keto Alcohols from the exudate of Campnosperma auriculata Hook. F

1958 ◽  
Vol 11 (1) ◽  
pp. 73 ◽  
Author(s):  
JA Lamberton
Keyword(s):  
Catalytic Hydrogenation ◽  
Active Component ◽  
General Structure ◽  
Optically Active ◽  
Side Chain ◽  
Active Compounds ◽  
Aliphatic Side Chain ◽  
Active Substances ◽  
Optically Active Substances ◽  
Long Chain

Terentang oil, the exudate from the Malayan tree Campnosperma auriculata Hook. f., contains optically active substances closely related to the optically active component of Tigaso oil. These substances are assigned the general structure I and differ among themselves only in the amount and location of unsaturation in the C19 aliphatic side chain. All of them by heating with ethanolic alkali and subsequent hydrogenation give a product which is mainly 3-nonadecyl phenol. Catalytic hydrogenation alone produces (+)-3-hydroxy-3-nonadecylcyclohexanone and thence by dehydration 3-nonadecylcyclohex-2-enone. Hydrocampnospermonol is a convenient starting material for the preparation of the reference substances 3-nonadecyl phenol and 3-nonadecylcyclohexanone.

Optically Active Compounds Related to Methadon

1949 ◽  
Vol 71 (2) ◽  
pp. 460-462 ◽  
Author(s):  
Albert. Pohland ◽  
Frederick J. Marshall ◽  
Thomas P. Carney
Keyword(s):  
Optically Active ◽  
Active Compounds

Chemoenzymatic Preparation of Optically Active Long-Chain 3-Hydroxyalkanoates

Biocatalysis ◽  
1990 ◽  
Vol 3 (1-2) ◽  
pp. 145-158 ◽  
Author(s):  
Clemens Feichter ◽  
Kurt Faber ◽  
Herfried Griengl
Keyword(s):  
Optically Active ◽  
Long Chain
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