• Bulletin of the Korean Chemical Society
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• v.33 no.6
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• pp.1834-1838
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• 2012

A facile route for the synthesis of dimethyl glutarate (DMG) from cyclobutanone and dimethyl carbonate (DMC) in the presence of solid base catalysts has been developed. It was found that the intermediate carbomethoxycyclobutanone (CMCB) was produced from cyclobutanone with DMC in the first step, and then CMCB was further converted to DMG by reacting with a methoxide group. The role of the basic catalysts can be mainly ascribed to the activation of cyclobutanone $via$ the abstraction of a proton in the ${\alpha}$-position by base sites, and solid bases with moderate strength, such as MgO, favor the formation of DMG.

• Food Science and Preservation
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• v.21 no.6
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• pp.859-865
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• 2014

This study was conducted to analyze the hydrocarbons and 2-alkylcyclobutanones as marker compounds in walnuts after the walnuts' exposure to ${\gamma}$ irradiation. The samples were irradiated with gamma rays at 0, 1, 3, 5, 7, and 10 kGy doses. The lipids were extracted via soxhlet extraction using hexane, and were separated by florisil column and identified via gas chromatography / mass spectrometry (GC/MS). The hydrocarbons that were detected were 8-heptadecene ($C_{17:1}$) and 1,7-hexadecadiene ($C_{16:2}$) from oleic acid and 8,11-heptadecadiene ($C_{17:2}$) and 1,7,10-hexadecatriene ($C_{16:3}$) from linoleic acid. The 2-alkylcyclobutanones that were detected were 2-dodecylcyclobutanone (DCB) from palmitic acid, 2-tetradecylcyclobutanone (TCB) from stearic acid, 2-(5'-tetradecenyl)cyclobutanone (TECB) from oleic acid, and 2-(5',8'-tetradecadienyl)cyclobutanone (5',8'-TCB) from linoleic acid. The correlation between the irradiation dose and the concentrations of the hydrocarbons and 2-alkylcyclobutanones in the walnuts was found to be linear. The radio-induced hydrocarbons and 2-alkylcyclobutanones were clearly detected in the irradiated walnuts at 1 kGy and above, but not in the non-irradiated ones. The major hydrocarbons obtained after irradiation were 8-heptadecene from oleic acid and 8,11-heptadecadiene and 1,7,10-hexadecatriene from linoleic acid, and the major 2-alkylcyclobutanones were TECB from oleic acid and 5',8'-TCB from linoleic acid. Therefore, these major compounds were concluded to be the marker compounds for determining the irradiated and non-irradiated samples.

• Journal of the Korean Society of Food Science and Nutrition
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• v.30 no.1
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• pp.37-42
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• 2001

Pinenut was irradiated with the dose of 0.5∼10 kGy. Radiation-induced hydrocarbons and 2-alkylcyclobutanones were extracted from pinenut, separated by florisil column chromatography and identified with GC/MS method. Concentrations of hydrocarbons and 2-alkylcyclobutanones were increased with the increase of irradiation dose and the composition of patty acids in pinenut affected on products detects. The major hydrocarbons in irradiated pinenut were 8-heptadecene and 1,7-hexadecadiene originated ferom oleic acid and 6,9-heptadecadiene and 1, 7, 10-hexadecatriene originated from linoleic acid. 2-(5'-Tetradecenyl) cyclobutanone originated from oleic acid was highest in the irradiated pinenut. Radiation-induced hydrocarbons hydrocarbons and 2-alkylcyclobutanones in pinenut were detected at 0.5 kGy and over, but not detected in the unirradiated samples.

• Preventive Nutrition and Food Science
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• v.4 no.4
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• pp.270-275
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• 1999

Radiation-induced hydrocarbons and 2-alkylcyclobutanones are formed from the fatty acids of irradiated fats. Peanuts were irradiated with a dose of 0.1∼10 kGy. The method consists of the extraction of fat from peanuts, separation of hydrocarbons and 2-alkylcyclobutanones with florisil column chromatography and identification of hydrocarbons by the GC/MS method and 2-alkylcyclobutanones by GC/MS/selected ion monitoring (SIM). Concentrations of hydrocarbons and 2-alkylcyclobutanones were linearly increased with the dose levels of radiation. The major hydrocarbons in the irradiated peanut samples were 8-heptadecene and 1,7-hexadecadiene from oleic acid and 6,9-heptadecadiene and 1,7,10-hexadecatriene from linoleic acid. 2-(5'-Tetradecenyl)cyclobutanone, one of 2-alkylcyclobutanones, was the highest amount in the irradiated peanuts. Radiation-induced hydrocarbons in the peanuts were detected at doses of 0.5 kGy and over, and radation-induced 2-alkylcyclobutanones were detected at doses of 1 kGy and over. These compounds were not confirmed in unirradiate peanuts.

• Korean Journal of Food Science and Technology
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• v.31 no.6
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• pp.1495-1502
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• 1999

Gamma-irradiated beef and chicken at the dose levels of 0.5 to 10 kGy were subjected to the detection of radiation-induced 2-alkylcyclobutanones whether irradiated or not. Radiation-induced 2-alkylcyclobutanones were extracted from beef and chicken fats, separated by florisil column chromatography and identified with GC/MS method by selected ion monitoring(SIM). When beef and chicken were irradiated, 2-dodecylcyclobutanone, 2-tetradecylcyclobutanone and 2-(5'-tetradecenyl)cyclobutanone were formed from palmitic, stearic and oleic acids. Concentrations of 2-alkylcyclobutanones were linearly increased with the dose levels of irradiation and depended upon the composition of fatty acids in beef and chicken. Radiation-induced 2-alkylcyclobutanones in irradiated beef and chicken were remarkably detected at 1 kGy and over, while these compounds were not detected in non-irradiated samples. The concentrations of radiationinduced 2-alkylcyclobutanones were relatively constant during 6 months.

• Journal of the Korean Society of Food Science and Nutrition
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• v.33 no.1
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• pp.158-163
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• 2004

We investigated the usefulness of 2-alkylcyclobutanones as markers for irradiated eggs and egg products by comparing 2-alkylcyclobutanone concentrations in irradiated raw egg yolk, boiled egg yolk, and egg yolk powder. One method of detection radiation-induced 2-alkylcyclobutanones involves extraction fat from irradiated egg samples separating 2-alkylcyclobutanones by florisil column chromatography, and identifying GC/MS. 2-(5'-Tetradecenyl)cyclobutanone of 2-alkylcyclobutanones was high relatively in boiled egg yolk, but 2-dodecylcyclobutanone was high in raw egg yolk and egg yolk Powder. Concentrations of the radiation-induced 2-alkylcyclobutanones increased linearly with the irradiation dose. The radiation-induced 2-alkylcyclobutanones from egg samples at 0.5 kGy over and not detected at the non-irradiated samples. Therefore, these compounds could be used as marker of Post-irradiation for egg Products.

• Journal of the Korean Society of Food Science and Nutrition
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• v.31 no.4
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• pp.599-603
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• 2002

Radiolytic compounds of lipids, as hydrocarbons and 2-alkylcyclobutanones, were determined to detect the irradiated dried Mytilus coruscus. The detection methods were composed of fat extraction by Soxtec apparatus from dried Mytilus coruscus, isolation of hydrocarbons and 2-alkylcyclobutanones with a florisil column chromatography and identification of GC/MS. Concentrations of the radiation-induced hydrocarbons and 2-alkylcyclobutanones increased with the irradiation dose. The major hydrocarbons in irradiated Mytilus coruscus were pentadecane and 1-tetradecene originated from palmitic acid, and heptadecane and 1-hexadecene originated from stearic acid. 2-(5'- Tetradecenyl)cyclobutanone of 2-alkylcyclobutanones was high relatively. The radiation - induced hydrocarbons and 2-alkylcyclobutanones from dried Mytilus coruscus were detected at 0.5 kGy over and not detected at the non-irradiated.