Ueda Oils and Fats Manufacturing Co.

Kōbe-shi, Japan

Ueda Oils and Fats Manufacturing Co.

Kōbe-shi, Japan
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Kaze N.,Ueda Oils and Fats Manufacturing Co. | Sato H.,Osaka Municipal Technical Research Institute | Yamamoto H.,Ueda Oils and Fats Manufacturing Co. | Watanabe Y.,Osaka Municipal Technical Research Institute
JAOCS, Journal of the American Oil Chemists' Society | Year: 2011

NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol was converted partly to 3-MCPD at the derivatization step conducted at 80 °C under acidic condition in the presence of NaCl. Based on the proton numbers observed by 1H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step. © 2011 AOCS.


Kaze N.,Ueda Oils and Fats Manufacturing Co. | Watanabe Y.,Osaka Municipal Technical Research Institute | Sato H.,Osaka Municipal Technical Research Institute | Murota K.,Kinki University | And 4 more authors.
Lipids | Year: 2016

The regioisomers of the di- and mono-oleate of monochloropropanediol (MCPD) have been synthesized and subsequently hydrolyzed with pancreatic lipase and pancreatin to estimate the intestinal digestion and absorption of these compounds after their intake. The hydrolysates were analyzed by HPLC using a corona charged aerosol detection system, which allowed for the separation and detection of the different regioisomers of the MCPD esters. The hydrolysates were also analyzed by GC–MS to monitor the free MCPD. The results indicated that the two acyl groups of 2-MCPD-1,3-dioleate were smoothly hydrolyzed by pancreatic lipase and pancreatin to give free 2-MCPD. In contrast, the hydrolysis of 3-MCPD-1,2-dioleate proceeded predominantly at the primary position to produce 3-MCPD-2-oleate. 2-MCPD-1-oleate and 3-MCPD-1-oleate were further hydrolyzed to free 2- and 3-MCPD by pancreatic lipase and pancreatin, although the hydrolysis of 3-MCPD-2-oleate was 80 % slower than that of 3-MCPD-1-oleate. The intestinal absorption characteristics of these compounds were evaluated in vitro using a Caco-2 cell monolayer. The results revealed that the MCPD monooleates, but not the MCPD dioleates, were hydrolyzed to produce the free MCPD in the presence of the Caco-2 cells. The resulting free MCPD permeated the Caco-2 monolayer most likely via a diffusion mechanism because their permeation profiles were independent of the dose. Similar permeation profiles were obtained for 2- and 3-MCPDs. © 2016 AOCS


Kaze N.,Ueda Oils and Fats Manufacturing Co. | Sato H.,Osaka Municipal Technical Research Institute | Yamamoto H.,Ueda Oils and Fats Manufacturing Co. | Watanabe Y.,Osaka Municipal Technical Research Institute
European Journal of Lipid Science and Technology | Year: 2011

By Deutsche Gesellschaft für Fettwissenschaft (DGF) standard methods C-III 18 for the determination of 3-monochloropropane-1,2-diol (3-MCPD), the minimum limit of detection was lower in the case of actual oil samples compared to the calibration samples. The problem was found to be lied in the low recovery of 3-MCPD derivatives from the aqueous phase to the organic phase at the extraction step of the standard procedure. The substitution of the conventional solvent, n-hexane, with n-butanol, chloroform, and ethyl acetate increased the recovery to the relative extent of 5.6, 4.7, and 3.9, respectively. The modification contributed to improve the accuracy of the method, especially at lower concentration (<1ppm) of 3-MCPD. Practical applications: This paper provides the modification of DGF standard methods C-III 18 in order to improve the accuracy to quantify 3-MCPD at lower concentration. It might be important for estimation and control of our daily intake of 3-MCPD, and for the product control in the fat and oil processing. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Sato H.,Osaka Municipal Technical Research Institute | Kaze N.,Ueda Oils and Fats Manufacturing Co. | Yamamoto H.,Ueda Oils and Fats Manufacturing Co. | Watanabe Y.,Osaka Municipal Technical Research Institute
JAOCS, Journal of the American Oil Chemists' Society | Year: 2013

Pure 2-monochloro-1,3-propanediol (2-MCPD) was successfully synthesized, identified, and first quantified by the Deutsche Gesellschaft für Fettwissenschaft (DGF) standard method C-VI 18 (10), with a calculable detection sensitivity relative to 3-monochloro-1,2-propanediol (3-MCPD) of 3.26-fold, using a QP-2010 GC/MS instrument. The detection sensitivities of other GC/MS instruments can be determined using the individual ion-ratio of the fragment to the precursor of 3-MCPD-d 5 as a reference. Quantification of 2-MCPD is possible using conventional 3-MCPD-d 5 esters as internal-standards, without a calibration curve of pure 2-MCPD. The dynamics of 2-MCPD during DGF standard methods C-VI 18 (10) were directly analyzed using NMR and indirectly using GC/MS. 2-MCPD was partly converted to glycidol under basic conditions of the transesterification step, and the glycidol was reconverted to 2-MCPD under acidic conditions of the extraction step. 2-MCPD spiked in soybean oil was detected as 98 mol% 2-MCPD and 2 mol% 3-MCPD from the area ratio in GC/MS. In contrast, glycidyl stearate spiked in soybean oil was detected as 5.5-5.7 mol% 2-MCPD and 94.3-94.5 mol% 3-MCPD from the corrected area ratio in GC/MS. © 2013 AOCS.


Honryo T.,Kinki University | Yamamoto H.,Ueda Oils and Fats Manufacturing Co. | Kumanishi A.,Ueda Oils and Fats Manufacturing Co. | Hirose H.,Ueda Oils and Fats Manufacturing Co. | Sawada Y.,Kinki University
Nippon Suisan Gakkaishi (Japanese Edition) | Year: 2012

It is important to produce safe cultured fish by reducing their dioxin content.We investigated the reduction of dioxin content in cultured red sea bream Pargus major by feeding artificial diets containing two sorts of fish oil with different dioxin content: CT (3 pg-TEQ/g) and MD (18 pg-TEQ/g). There was no significant difference in the growth, survival, and feeding indices between the CT and MD fed groups. The content of dioxins in the muscle significantly decreased in the CT fed group (0.07 pg-TEQ/g) compared with the initial content (0.14 pg-TEQ /g), whereas that in the MD fed group increased to 0.30 pg-TEQ/g. This esffect was particulary clear in the liver. These results demonstrated the possibility of producing cultured fish with low content of dioxins by feeding lowdioxin fish oil.

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