Formation and occurrence of esters of 3‐chloropropane‐1,2‐diol (3‐CPD) in foods: What we know and what we assume

Abstract

Although chloropropanols have historically been associated with the savoury food ingredient hydrolyzed vegetable protein (HVP), prepared by acid hydrolysis, the discovery of significant amounts of 3-chloropropane-1,2-diol (3-CPD) 'bound' as fatty acid esters in foodstuffs (3-CPD esters), especially in refined edible oils, is still a relatively recent discovery. The toxicological significance of these 3-CPD esters and their potential contribution to the dietary intake of non-esterified 3-CPD is not yet known and this review considers their likely metabolic fate in vivo. The latest developments in methods of analysis are presented while the occurrence of CPD esters and their potential formation mechanisms are discussed in detail. The generation of related compounds, possible measures of control and the future outlook are also considered.Practical application: Comprehensive and up to date information concerning the state of the art with respect to the occurrence of esters of chloropropanediols in foods presented all in one place. This concise review of toxicological aspects, methods of analysis, occurrence, formation routes and potential measures of control provides data for practical use by professionals engaged in research, surveillance, risk management and regulation of these contaminants in foods.

3-Chloropropane-1,2-diol fatty acid esters in potato products

“…Furthermore, it is known that refined vegetable oils, especially palm oil, contain high amounts of 3-CPD esters formed during deodorisation and may thus contaminate deep-fried foods (Hamlet et al 2011).…”

Chloropropanols, Chloropropandiols and Their Esters in Food – Formation, Occurrence, Determination, Reduction of Content

“…Obecnie przyjmuje się, że istnieją cztery podstawowe mechanizmy powstawania estrów 3-MCPD, głównie w schemacie: diacyloglicerol + jon chlorkowy → ester 3-MCPD. Mechanizmy te polegają na substytucji nukleofilowej SN2 anionu chlorkowego w cząsteczkach acylogliceroli [34,59]. Dwa z proponowanych mechanizmów polegają na bezpośrednim nukleofilowym oddziaływaniu Cl¯ na glicerolowy atom węgla w acyloglicerolu, połączony z grupą estrową albo z grupą hydroksylową (rys.…”

“…Glicydol (2,3-epoksy-propan-1-ol) w obecności HCl i pod wpływem ciepła może ulegać interkonwersji pomiędzy 3-MCPD i 2-MCPD. Mechanizmy powstawania MCPD i DCP oraz ich estrów zostały przedstawione w wielu publikacjach [9,14,34,59,60,67,71]. Analizowana jest także możliwość udziału związków chloroorganicznych rozpuszczalnych w fazie olejowej w powstawaniu 3-MCPD i jego estrów [53,58].…”

“…[29], a 3-MCPD związanego w postaci estrów w żywności -także Hamlet i wsp. [34]. Nowe dane dotyczące zawartości estrów 3-MPCD w żywności zawierają prace grupy autorów stowarzyszonych w Międzynaro-dowym Instytucie Nauk o Życiu [12] oraz MacMahona i wsp.…”

Mitigation role of erythritol and xylitol in the formation of 3-monochloropropane-1,2-diol and its esters in glycerol and shortbread model systems

“…The content of 3-MCPD esters usually significantly exceeds that of free 3-MCPD; in shortbread, the level of free 3-MCPD is about 70 μg kg , while 3-MCPD esters can reach even 632 μg kg −1 [14]. 3-MCPD esters can be present in fats, oils, or margarine used for shortcrust pastry production [15][16][17][18], but they might also be generated upon heat treatment as the effect of the reaction between triacylglycerols (TAG)/diacylglycerols (DAG)/monoacylglycerols (MAG) and glycerol and chloride ions originating from NaCl added or residual (natural) salt present in raw materials [18]. Although a detailed mechanism of these reactions has not been yet clearly explained, five routes of 3-MCPD ester formation have already been proposed.…”