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J Biosci Bioeng. 2016 Aug;122(2):246-51. doi: 10.1016/j.jbiosc.2015.12.018. Epub 2016 Jan 25.

Insights into the formation mechanism of chloropropanol fatty acid esters under laboratory-scale deodorization conditions.

Author information

1
Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan; Fuji Oil Co., Ltd., 1 Sumiyoshi-Cho, Izumisano, Osaka 598-8540, Japan. Electronic address: hori.katsuhito@so.fujioil.co.jp.
2
Fuji Oil Co., Ltd., 1 Sumiyoshi-Cho, Izumisano, Osaka 598-8540, Japan. Electronic address: koriyama.natsuko@so.fujioil.co.jp.
3
Fuji Oil Co., Ltd., 1 Sumiyoshi-Cho, Izumisano, Osaka 598-8540, Japan. Electronic address: tsumura.kazunobu@so.fujioil.co.jp.
4
Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan. Electronic address: fukusaki@bio.eng.osaka-u.ne.jp.
5
Department of Biotechnology, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan; Medical Institute of Bioregulation, Kyusyu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan. Electronic address: bamba@bioreg.kyushu-u.ac.jp.

Abstract

Chloropropanol fatty acid esters (CPFAEs) are well-known contaminants in refined oils and fats, and several research groups have studied their formation. However, the results obtained in these studies were not satisfactory because the CPFAEs were not analyzed comprehensively. Thus, in the present study, a comprehensive analysis was performed to obtain new details about CPFAE formation. Each lipid (monopalmitin, dipalmitin, tripalmitin, monoolein, diolein, triolein, and crude palm oil) was heated at 250°C for 90 min, and the CPFAEs were analyzed using supercritical fluid chromatography/tandem mass spectrometry. It was found that CP fatty acid monoesters were formed from monoacylglycerols and diacylglycerols after heating in the presence of a chlorine compound. In addition, CP fatty acid diesters were formed from diacylglycerols and triacylglycerols under the same conditions. In the case of crude palm oil, only CP fatty acid diesters were formed. Therefore, these results indicated that CPFAEs in refined palm oil were formed mainly from triacylglycerols.

KEYWORDS:

Acylglycerols; Chloropropanol fatty acid esters; Heating; Supercritical fluid chromatography/mass spectrometry

PMID:
26822095
DOI:
10.1016/j.jbiosc.2015.12.018
[Indexed for MEDLINE]

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