Determination of 3-chloropropane-1,2-diol in liquid hydrolysed vegetable proteins by capillary gas chromatography with flame ionization detection

Plantinga, W.J.; Toorn, W.G. Van; Stegen, G.H.D. van der

doi:10.1016/s0021-9673(01)87196-x

Cited by 35 publications

(14 citation statements)

References 3 publications

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“…The method of PLANTINGA et al (1991) was employed with a slight modification. One ml of sample and 1 ml of internal standard solution (propane-1,3-diol, 1 mg per ml in 20% sodium chloride solution) were heated for 20 minutes at 90°C with 0.4 ml phenylboronic acid in acetone in a 5 ml flask.…”

Section: Methodsmentioning

confidence: 99%

Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates

Velı́šek¹,

Doležal²,

Crews³

et al. 2002

Czech J. Food Sci.

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Protein hydrolysates produced by hydrochloric acid hydrolysis were analysed for 3-chloropropane-1,2-diol and its enantiomers. It was found that (R)-3-chloropropane-1,2-diol and (S)-3-chloropropane-1,2-diol were present in the hydrolysates in equimolar concentrations. Model experiments with glycerol, triolein and soy lecithin heated with hydrochloric acid in solution showed that these materials were precursors of 3-chloropropane-1,2-diol and 2-chloropropane-1,3-diol and, as expected, yielded racemic 3-chloropropane-1,2-diol. Yields of 3-chloropropane-1,2-diols decreased in the order triolein > lecithin > glycerol. The mechanisms of 3-chloropropane-1,2-diol enantiomers formation during the production of protein hydrolysates are presented and discussed as well as the reaction pathways of their decomposition in alkaline media via the corresponding intermediates, (R)-and (S)-glycidol, respectively. Both epoxides are hydrolysed to glycerol and form a variety of products with hydrolysate constituents.

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Section: Methodsmentioning

confidence: 99%

Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates

Velı́šek¹,

Doležal²,

Crews³

et al. 2002

Czech J. Food Sci.

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“…Plantinga et al 7 improved a method for the determination of 3-MCPD derivativized by phenylboronic acid (PBA) in liquid HVP using capillary gas chromatography (GC) with flame ionization detection.…”

Section: Resultsmentioning

confidence: 99%

“…The PBA derivative procedure was used based on the description reported by Plantinga et al 7 Briefly, a 100 µL stock solution was added into a 10 mL sodium chloride solution in a 150-mL conical flask.…”

Section: Experiments Processmentioning

confidence: 99%

Determination of 3-Chloropropane-1,2-diol in Liquid Hydrolyzed Vegetable Proteins and Soy Sauce by Solid-Phase Microextraction and Gas Chromatography/Mass Spectrometry

Huang

Jiang

et al. 2005

ANAL. SCI.

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Headspace solid-phase microextraction (HS-SPME) coupled with gas chromatography/mass spectrometry (GC/MS) method was developed to determine 3-chloropropane-1,2-diol (3-MCPD) in hydrolyzed vegetable protein and Chinese soy sauce. The 3-MCPD was firstly derivativized with phenylboronic acid in aqueous solution at 90˚C for 10 min, then extracted by HS-SPME and finally detected with GC/MS, parameters related to both the derivative reaction and the HS-SPME process were optimized. The proposed method has a linear range of 0.0194 -394 µg g -1 , a detection limit of 3.87 ng g -1 (S/N = 3), and a precision of RSD = 7.5% (n = 5). Seventeen real samples, including four HVPs and thirteen soy sauce samples, were analyzed to examine the feasibility of the proposed procedure; with a concentration of 3-MCPD and acceptable recoveries at 0.71 µg g -1 spiked levels were obtained. Being simpler, faster and more environmentally benign than the existing methods, this method is accurate and suitable for routine analysis.

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“…Analytical methods used to determine 3-MCPD include: gas chromatography (GC) of an alkyl or phenyl boronic acid derivative with electron-capture detection, 5,6 flame ionization detection 7 and mass detection; 8,9 GC of a heptafluorobutyrate derivative with electron-capture detection; 10 GC of the underivatized diol with electrolytic conductivity detection 11 or mass detection. 12 However none of these methods are of sufficient sensitivity or selectivity for the determination of µg/kg levels of 3-MCPD in HVP.…”

mentioning

confidence: 99%

“…Based on the capillary GC analysis of a heptafluorobutyryl derivative the method is more sensitive and selective than any procedure currently available. Preparation of 3-chloro-1,2-propandiol-d 7 3-Chloro-1,2-propandiol-d 7 was prepared using deuterated starting materials ( > 98 atom %) in 42% yield according to the procedure described by Conant and Quale. 16 Vacuum distillation of the reaction products gave a pale yellow liquid b.pt.…”

mentioning

confidence: 99%

Determination of the Chloropropanols, 3-Chloro-1,2-propandiol and 2-Chloro-1,3-propandiol, in Hydrolysed Vegetable Proteins and Seasonings by Gas Chromatography/Ion Trap Tandem Mass Spectrometry

Hamlet

Sutton

1997

Rapid Commun. Mass Spectrom.

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This paper reports on the development of a highly selective method for the determination of parts-per-billion (µg/kg) levels of 3-chloro-1,2-propandiol (3-MCPD) in hydrolysed vegetable proteins (HVP) using gas chromatography/ion trap mass spectrometry operating in the tandem mass spectrometry (MS/MS) mode. Samples were extracted into 5M sodium chloride solution and partitioned into diethyl ether using Extrelut® 20 solid phase columns. Dried and concentrated extracts were derivatized with heptafluorobutyrylimidazole (HFBI) prior to determination by gas chromatography ion trap (GC/IT) MS/MS. Multiple reaction monitoring was used to monitor the parent/daughter ion transitions of the analytes and the stable isotope internal standard (3-chloro-1,2-propandiol-d 7 ). Calibration was linear over the range 5.0-500 pg/µL with correlation coefficients of 0.999 routinely obtained. The results showed that the method was capable of detecting 3-MCPD below 5 µg/kg in HVP when analysed by GC/ITMS/MS.

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Determination of 3-chloropropane-1,2-diol in liquid hydrolysed vegetable proteins by capillary gas chromatography with flame ionization detection

Cited by 35 publications

References 3 publications

Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates

Optical isomers of chloropropanediols: mechanisms of their formation and decomposition in protein hydrolysates

Determination of 3-Chloropropane-1,2-diol in Liquid Hydrolyzed Vegetable Proteins and Soy Sauce by Solid-Phase Microextraction and Gas Chromatography/Mass Spectrometry

Determination of the Chloropropanols, 3-Chloro-1,2-propandiol and 2-Chloro-1,3-propandiol, in Hydrolysed Vegetable Proteins and Seasonings by Gas Chromatography/Ion Trap Tandem Mass Spectrometry

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