Branched-Chain Fatty Acids. III. New Method of Introducing the Branching Methyl Group. Synthesis of 15-Methyloctadecanoic Acid and 14-Methyltetracosanoic Acid

Cason, James; Adams, Clark E.; Bennett, L. Lee; Register, U. D.

doi:10.1021/ja01238a044

Cited by 24 publications

(12 citation statements)

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“…There are several synthetic methods described for the synthesis of 4-methyl alkanoic acids and esters. Compounds 1 and 3 were prepared by Cason et al (1944) by reaction of ethyl levulinate or levulinic acid with the corresponding Grignard reagent to produce a /,,'y-dialkylbutyrolactone.…”

Section: Discussionmentioning

confidence: 99%

Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

et al. 1995

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Abstract-Male coconut rhinoceros beetles, Orycres rhinoceros (L.), produce three sex-specific compounds, ethyl 4-methyloctanoate, ethyl 4-methylheptanoate, and 4-methyloctanoic acid, the first of which is an aggregation pheromone. Synthesis of these compounds involving conjugate addition of organocuprates to ethyl acrylate is reported. In field trapping experiments, (4S)-ethyl 4-methyloctanoate and the racemic mixture were equally attractive and 10 times more effective in attracting beetles than ethyl chrysanthemumate, a previously recommended attractant. Ethyl 4-methylheptanoate was as attractive as ethyl chrysanthemumate and more attractive than 4-methyloctanoic acid, but further studies are required before it can be classed as an aggregation pherornone. Compared to ethyl 4-methyloctanoate alone, combinations of the three male-produced compounds did not increase attraction, whereas addition of freshly rotting oil palm fruit bunches to pheromone-baited traps sjgnificantly enhanced attraction. With increasing dose, captures of O. rhinocerós'increased, but doses of 6, 9, and 18 mg/day were competitive with 30 mg/day lures. Newly designed vane traps were more effective in capturing beetles than were barrier or pitfall traps. Results of this study indicate that there is potential for using ethyl 4-methyloctanoate in operational programs to control O. rhinoceros in oil palm plantations.

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Section: Discussionmentioning

confidence: 99%

Aggregation pheromone of coconut rhinoceros beetle,Oryctes rhinoceros (L.) (coleoptera: Scarabaeidae)

et al. 1995

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“…Synthesis of 4-Methyloctanoic and 4-Methylnonanoic Acids. 4-Methyloctanoic and 4-methylnonanoic acids were synthesized from ethyl levulinate and the appropriate Grignard reagent according to the general method described by Cason et al (1944). Treatment of the resulting , -disubstituted butyrolactone with thionyl chloride and ethanolic HC1 resulted in the branched unsaturated ester.…”

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confidence: 99%

Volatile medium chain fatty acids and mutton flavor

Wong¹,

Nixon²,

Johnson³

1975

J. Agric. Food Chem.

148

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Mutton fat, cooked with or without meat added, produced a host of steam volatile fatty acids in trace amounts. These have been identified by GC-MS as medium chain normal, branched, unsaturated, oxygenated, and aromatic acids belonging to 11 homologous series. Odor properties of these acids have been evaluated and results in-dicate that the branched chain and unsaturated acids having 8 to 10 carbon atoms contribute to the undesirable flavor of cooked mutton. The 4-methyl branched Cg and Cio acids in particular are considered primarily responsible for the sweaty odor note described in Chinese as "SOO".

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“…Found: C, 58.35; H, 7.53. In similar experiments involving quantities from 0.08 to 0.4 mole the yields were 74-88%, the higher yields being obtained w'hen a large excess of thionyl chloride was used. When approximately the theoretical amount (22) of thionyl chloride was used, some lactone (XIV) wras recovered (10-18%); wdth the large excess of thionyl chloride no appreciable amount of lactone was detected in the product. When the alcohol was omitted from the hydrolysis mixture, the time for complete hydrolysis was about five hours.…”

Section: Methodsmentioning

confidence: 99%