The knowledge of chloropropanediols (MCPD) fatty acid esters formation pathways is an important condition for these processing contaminants mitigation. This study aimed to assess the potential of a group of lipophilic environmental contaminants, polychlorinated alkanes, commonly known as chlorinated paraffins (CPs), to contribute to the formation of MCPD esters. Laboratory-scale model systems representing vegetable oils contaminated with both a technical mixture of short-chained CPs and individual short-chained CPs were designed and subjected to heat treatment (230 °C, 2 h) to simulate the deacidification and deodorisation processes. A substantial increase in MCPD content (up to 3.4 times the control levels) was observed in systems spiked with a technical mixture. MCPD formation seems to correlate very well with the concentration of CPs in these systems. Based on the generated data, we can conclude that the processing of vegetable oils contaminated with CPs might contribute to elevated concentrations of MCPD.

• Klíčová slova
• Chlorinated paraffin, Chloropropanediol (MCPD) ester, Polychlorinated alkane, Precursor, SCCP, Vegetable oil, Vegetable oil refining,
• MeSH
• alfa-chlorhydrin * analýza   chemie   MeSH
• chlor chemie   MeSH
• chlorované uhlovodíky chemie   analýza   MeSH
• kontaminace potravin * analýza   MeSH
• oleje rostlin * chemie   MeSH
• parafín * chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• alfa-chlorhydrin * MeSH
• chlor MeSH
• chlorované uhlovodíky MeSH
• oleje rostlin * MeSH
• parafín * MeSH

The influence of dough composition on acrylamide, 3-monochloropropane-1,2-diol (3-MCPD) esters, and glycidyl esters (GE) formation during bread toasting was investigated. The doughs differed in added amounts of soy lecithin, salt, and reducing agents (l-cysteine and glutathione). The toasting of bread for 2.5 min considerably enhanced the formation of acrylamide and 3-MCPD esters. The addition of lecithin (1%, w/w) resulted in four times higher content of 3-MCPD esters in toasted bread slices. No distinct relationship between dough composition and GE formation in untoasted and toasted bread was found. The addition of reducing agents (0.05%, w/w) mitigated during toasting not only the formation of 3-MCPD esters (more than six times) but also the extent of Maillard reaction that resulted in three times lower amounts of acrylamide and predominant formation of alcohol-like compounds. Toasted bread without reducing agents contained typical Maillard reaction compounds such as aldehydes, alkyl pyrazines, and derivatives of furan.

• Klíčová slova
• 3-MCPD esters, Acrylamide, Glutathione, Glycidyl esters, L-cysteine, Soy lecithin, Toasted bread, Volatile compounds,
• MeSH
• akrylamid analýza   MeSH
• alfa-chlorhydrin analýza   MeSH
• chléb analýza   MeSH
• estery analýza   MeSH
• glutathion chemie   MeSH
• lecitiny chemie   MeSH
• Maillardova reakce MeSH
• mikroextrakce na pevné fázi MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• pšenice chemie   metabolismus   MeSH
• Saccharomyces cerevisiae metabolismus   MeSH
• těkavé organické sloučeniny analýza   izolace a purifikace   MeSH
• vaření metody   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• akrylamid MeSH
• alfa-chlorhydrin MeSH
• estery MeSH
• glutathion MeSH
• lecitiny MeSH
• těkavé organické sloučeniny MeSH

3-MCPD esters are contaminants that can form during refining of vegetable oils in the deodorization step. It was experimentally shown that their content in the vegetable oil depends on the acid value of the vegetable oil and the chloride content. 3-MCPD esters form approximately 2-5 times faster from diacylglycerols than from monoacylglycerols. It has been proved that the higher fatty acids content in the oil caused higher 3-MCPD esters content in the deodorization step. Neutralization of free fatty acids in the vegetable oil before the deodorization step by alkaline carbonates or hydrogen carbonates can completely suppress the formation of 3-MCPD esters. Potassium salts are more effective than sodium salts.

• Klíčová slova
• 2-Diol, 2-Dipalmitate, 3-CPD esters, 3-Chloropropane-1, 3-MCPD esters, Deodorization, Palm oil, Refining,
• MeSH
• alfa-chlorhydrin analýza   chemická syntéza   MeSH
• chloridy analýza   MeSH
• diglyceridy chemie   MeSH
• estery MeSH
• kyseliny mastné neesterifikované chemie   MeSH
• manipulace s potravinami metody   MeSH
• mastné kyseliny analýza   MeSH
• odoranty MeSH
• oleje rostlin chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• alfa-chlorhydrin MeSH
• chloridy MeSH
• diglyceridy MeSH
• estery MeSH
• kyseliny mastné neesterifikované MeSH
• mastné kyseliny MeSH
• oleje rostlin MeSH

A series of twelve breast milk samples were analysed by gas chromatography-mass spectrometry (GC/MS) operated in selected ion monitoring mode for 3-chloropropane-1,2-diol (3-MCPD). Whilst none of the samples contained 3-MCPD above the limit of detection of 3 microg kg(-1) milk, all contained high amounts of 3-MCPD esterified with higher fatty acids. The levels of 3-MCPD released by hydrolysis of these esters (bound 3-MCPD) ranged from the limit of detection (300 microg kg(-1), expressed on a fat basis) to 2195 microg kg(-1); with a mean level of bound 3-MCPD of 1014 microg kg(-1), which corresponded to 35.5 microg kg(-1) milk. The presence of bound 3-MCPD was confirmed using orthogonal gas chromatography coupled with high-speed time-of-flight mass spectrometry analysis for four randomly selected breast milk samples. Six breast milks collected from one of the nursing mothers 14-76 days after childbirth contained bound 3-MCPD within the range of 328-2078 microg kg(-1) fat (mean 930 microg kg(-1) fat). The calculated bound 3-MCPD content of these samples was within the range of 6 and 19 microg kg(-1) milk (mean of 12 microg kg(-1) milk). The major types of 3-MCPD esters were the symmetric diesters with lauric, palmitic, and oleic acids, and asymmetric diesters with palmitic acid/oleic acid among which 3-chloro-1,2-propanediol 1,2-dioleate prevailed.

• MeSH
• alfa-chlorhydrin analýza   MeSH
• analýza potravin metody   MeSH
• dospělí MeSH
• kontaminace potravin analýza   MeSH
• lidé MeSH
• lipidy analýza   MeSH
• mateřské mléko chemie   MeSH
• mladiství MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí metody   MeSH
• Check Tag
• dospělí MeSH
• lidé MeSH
• mladiství MeSH
• ženské pohlaví MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• alfa-chlorhydrin MeSH
• lipidy MeSH