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TOXIC SUGAR DERIVATIVES PRODUCED DURING MAILLARD REACTION AND
ITS IMPLICATIONS ON HUMAN HEALTH
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INTRODUCTION

The Maillard reaction, named after L
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Maillard, is also known as non-enzymatic browning
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The Maillard reaction begins with the reaction of reducing sugars with amines to form
glycosylamines (Mailard, 1912)
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The reaction is sequential, forming
highly reactive intermediates that then react in a variety of ways
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The Maillard reaction also occurs at room temperature, but is much slower
and slowest at low temperatures, low pH, and low Aw values (Naresh et al, 2017)
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The sulfur-containing amino acids methionine and cysteine play a central role in the
formation of the highly flavored components obtained in the Maillard reaction
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Unsaturated fatty acids and aldehyde fatty acid components also contribute to the formation of
odorous heteroaromatic compounds during the Maillard reaction (Naresh et al
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1
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It is
widely used in food due to its role in producing color, flavor, texture and other functional
properties
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The Maillard reaction is important in the food industry as it is associated with aroma,
flavor and color, especially in traditional processes such as roasting coffee and cocoa beans, baking
bread and cakes, toasting grains and cooking meat
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2013)
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These
products are also used to improve protein properties
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2013)
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2

Chemistry of the Maillard Reaction

This reaction is dependent on physical parameters such as heat, humidity, pH and NH2 and
produces sophisticated compounds not naturally found in food
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The Maillard reaction can be divided into three stages
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In the early stages, colorless products like sugar-amine
condensations, i
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N-glycoside compounds, are formed
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This reaction is
known as the Amadori rearrangement and yields 5-hydroxymethylfurfural, reductones and
dicarbonyl compounds
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Coloration occurs
during the thermal conversion of sugars due to a pH-scaled response to sugar groups, but amino
acids are not directly responsible for coloration (Adrian
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The characteristic color of foods
such as coffee, malt, bread, cocoa, and a variety of cooked foods is due to melanoidins, which are
massive brown nitrogen pigments (Bastos et al
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The final and intermediate steps are the
most crucial for creating flavor and aroma through Strecker degradation, in addition to desired
color (Somoza
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2

Three Steps of Maillard Reaction
Initial Step

Intermediate Step

Final Step

Fig 1: Mechanism of Maillard reaction

1
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The Maillard process also occurs
in living cells, hence the term "glycation" is used to distinguish between protein enzymatic
glycosylation in living cells and nonenzymatic glycosylation in food
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AGEs play a role in a number of disorders (i
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, pathophysiological processes)
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1
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Early on in the Maillard reaction, lysine derivatives such N-lactulosyllysine, N-fructosyllysine, or
N-maltulosyllysine are the main reaction products
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Glyoxal,
methylglyoxal, and 3-deoxyglucosulose are examples of 1,2-dicarbonyl molecules that are created
during the intermediate stage
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N-carboxymethyllysine
(CML), pyrraline, pronyl-lysine, pentosidine, gyloxal-lysine-dimer, methylglyoxal-lysine-dimer,
and 3-deoxyglucosulose-lysine-dimer are among the AGEs that are detected in meals (figure 2)
...
2 Chemical structure of CML and pyrraline
Pyralines are heterocyclic AGEs formed by the reaction of the ε-amino group of lysine with 3deoxyglucosulose
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N-ε-Carboxymethyllysine (CML) was the first advanced Maillard reaction amino acid
derivative formed by oxidative cleavage of the Amadori product
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4

Heat treatment and subsequent storage of milk changes lysine by 10-20%
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Lysine derivatives such as N-ε-fructoseridine and N-εmaltuloceridine are found in baked goods
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Pyralin concentrations detected ranged from 150 mg/kg protein in
sterilized milk to 3,700 mg/kg protein in bread crusts
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2
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1

Maillard reaction Products

Amadori compounds, which are the primary form of glycation chemicals, are found in meals
containing protein that experience early Maillard reactions
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The pathogenesis of diabetes and associated biological conditions,
such as cataract, joint rigidity, or diabetic nephropathy, were related to the glycation process that
takes place in vivo
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However, there is disagreement regarding a dietary glycation compound's toxicological
impact
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Healthy individuals' bodies slowly produce AGEs, however this
process advances more favorably when dietary Maillard reaction products are present
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As a result, there is a concern about the safety
of AGEs in food (Sebekova and Somoza 2007)
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2

Hydroxymethylfurfural (HMF)

The Maillard reaction's intermediate hydroxymethylfurfural (5-hydroxymethyl-2-furaldehyde,
HMF) is naturally produced during heating (MR)
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11 g/mol
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HMF is created during
the heating process and subsequent storage of carbohydrate-rich goods
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Acidic foods have a
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significant potential for producing HMF
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By way of the Maillard reaction, caramelization, or pyrolysis of either
reducing moieties of disaccharides or free monosaccharides, sugars break down into furfural
molecules (Morales 2009)
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H
1

O
2

5

O

OH
3

4

Fig 3
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However, it is uncertain whether human
exposure to HMF poses a risk to their health, and there is no information available from
epidemiological research or case reports about a possible connection between HMF and an
increased risk of developing cancer in people
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2013)
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5 mg of body weight per day for a 60 kg
individual
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1984)
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3

Hazards of Furan

Furan is a colorless compound with a molecular weight of 68 and a boiling point of 31 C
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A significant class of chemicals that are produced during the Maillard reactions
in foods are furans (Maga 1979)
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Furan is created through a variety of processes, including the thermal oxidation of ascorbic
acid, polyunsaturated fatty acids, and carotenoids, as well as the thermal degradation of certain
amino acids and reducing sugars like glucose, lactose, and fructose (Vranová and Ciesarová,
2009)
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According to Becalski
and Seaman (2005), the oxidation of polyunsaturated fatty acids (PUFAs) at high temperatures can
result in the synthesis of furan, however the addition of commercially available antioxidants (such
tocopherol acetate) can inhibit the formation of furan by up to 70%
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In the 1960s and 1970s, parent furan was
discovered in a few heat-treated foods, including coffee, canned meat, bread, cooked chicken,
sodium caseinate, hazelnuts, hydrolyzed soy protein, rapeseed protein, fish protein concentrate,
and caramel (Maga)
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Toxicity of Furan
The production of hepatic cholangiocarcinomas in rats and mice is the most notable tumor that
furan induces in animal experiments (Vranová and Ciesarová 2009)
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(Group 2B)
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Furan is swiftly absorbed by the body, but it is also efficiently eliminated
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Heterocyclic Aromatic Amines

More than 25 HCAs have been isolated and identified in cooked meat products since Japanese
scientist Sugimura first detected carcinogenic and/or mutagenic heterocyclic aromatic amines
(HCAs/HAAs) in fish and meat cooked at temperatures over 150 C in 1977
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2008)
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Some HAAs, including 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2amino-3,4-dimethylimidazo[4,5-f]quinoline

(MeIQ),

and

2-amino-1-methyl-6-

phenylimidazo[4,5-b]pyridine (PhIP), have been classified by the International Agency for
Research on Cancer as probable human carcinogens and class 2A, respectively (Kizil et al
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Aminoimidazoazoarenes (AIAs), also known as imidazoquinoline (IQ)-type compounds
or thermic HCAs, and aminocarbolines, sometimes known as non-IQ-type HCAs, are two basic
categories into which HCAs can be divided
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They contain a quinoline, quinoxaline, or pyridine attached to an
imidazo group
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2017)
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According to Sugimura and Adamson (2000), the production of
them is significantly influenced by the type of meat, its fat and moisture content, pH, sugar, free
amino acid, and creatinine content, lipid oxidation, and the presence of antioxidants (Kizil et al
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Toxicity of Heterocyclic Aromatic Amines in Food
Salmonella's mutagenicity was affected by the number and locations of exocyclic substituents,
particularly the 2-amino-group of the imidazo portion of the chemical structure present in most
HCAs, and varied between the strongest and weakest HCAs by more than 160,000 times (Nagao
et al
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HCAs have been discovered to be powerful carcinogens that, after prolonged oral
exposure, cause a range of tumor histologies in numerous organs (Sugimura and Adamson 2000)
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Additionally, strong
epidemiological data link a high consumption of HCAs to colon cancer, however this relationship
is not always reliable (Margaretha and Kerstin 2005)
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Meat and fish cooked at home are the
main food sources of human exposure to HAAs
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2
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08 that is made up of a reactive
ethylenic double bond coupled to a carboxamide group (IARC 1994)
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3 kPa/25 mmHg and a melting point of 84
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3 C
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A
reactive electrophilic double bond and an amide group are both present in the difunctional
monomer acrylamide (Habermann, 1991)
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The Maillard reaction appears to produce
acrylamide as an unwanted byproduct
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2000)
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After condensation with reducing sugars or a carbonyl source in cooked foods, the
asparagine is mostly to blame for the creation of acrylamide (Gokmen and Palakzaglu 2008)
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2005)
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(2003), acrylamide can be created from meals that include oils and nitrogencontaining chemicals, such as acrolein, which is created when glycerol is thermally degraded
(Umano and Shibamoto 1987)
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Even within one food category, such
as potatoes, the amount of asparagines varies widely, and the amount of acrylamide also varies
greatly
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Processed foods with high acrylamide content include bread crust, crisp bread, tortilla
chips, potato chips, French fries, various baked products, coffee, and cereal formulas
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(Kerstin and Margaretha
2005)
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3 to 0
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Rice (2005) examined
acrylamide's carcinogenicity
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Glycidamide causes
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bacterial mutation
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According to IARC (1994), acrylamide and its metabolite
glycidamide bind to hemoglobin and DNA in mice and rats, causing covalent adducts to form
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2
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Early in the 1960s, acrolein
was found in samples made from lipids that had undergone pyrolysis
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When food is heated, it is created
from carbs, animal and vegetable fats, and amino acids
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According to Esterbauer et al
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According to reports, acrolein can occur when food is processed at 100 degrees
Fahrenheit with a neutral pH
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As a result of the reaction between amino acids and carbonyls, Maillard reactions are in
charge of producing the cooked flavor in a variety of heated food products
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Additionally, the production of acrolein is caused by the processing of lipid-rich foods as well as
cooking techniques such deep-fat frying (Shibamoto 2009), particularly in the air
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5 to 30 mg/m3 in the air 15 cm above heated oil
(Shibamoto 2009)
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Acrolein was proposed to
form at high temperatures by the dehydration of glycerol (Izard and Libermann 1978); it may also
form by the oxidative breakdown of different fatty acids via radical chain mechanism, which is
more likely to happen at high temperatures and involves hemolytic fission of R-O bonds (Frankel
1982)
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As it develops from lipids like
cooking oils and lipid-rich meals like beef and pork that are processed at high temperatures,
acrolein is frequently found in outdoor air as well as interior air pollution, and its main issue is
inhalation toxicity
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09 (eye irritation) to 0
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15 mg/kg (0
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1977)
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3 to 33 mg/kg (Bioassay Systems Corporation 1981)
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1999) were also discovered
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Nitrates, Nitrites, and Nitrosamines

In preserved meats, nitrates and nitrites are added as food additives to stop the growth of bacteria
that produce botulinum toxin
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A variety of nitrosamines are
created when nitrates and secondary amines react
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Dimethyl-nitrosamine was
produced when the methylamines in the fish meal combined with sodium nitrite
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The primary chemical process that produces N-nitrosamines is the reaction of
secondary amines with nitrous acid
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The nitrate, which is frequently found in trace amounts in water and food, can be reduced by
enzymes to generate nitrous acid, or sodium nitrite, a preservative, can also do the same (Richard
and Phillip 1975)
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Nitrous acid is produced from nitrite in acidic environments and can be reacted
with amine to produce nitrosation reactions
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Fried bacon that has been nitrite-cured may experience nitrosation reaction
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Two
nitrosamines that are frequently discovered in cooked meals are N-nitrosodimethylamine (NDMA)
and N-nitrosopyrrolidine (NPYR)
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The presence of N-nitrosatable amines and nitrosating
agents has a significant impact on the production of nitrosamine in food
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However, the majority of N-nitroso substances found in food are nonvolatile and nonmutagenic
but may serve as precursors to volatile carcinogenic nitrosamines (e
...
, proteins with N-nitrosated
peptide links, such as N-nitrosoproline) (Margaretha and Kerstin 2005)
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The amount of NPYR generated
increases with higher temperatures and longer cooking times (Margaretha and Kerstin 2005)
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Toxicity of Nitrates, Nitrites, and Nitrosamines
NDMA is the most abundant N-nitrosamine in food and the major contributor to total human
exposure to volatile N-nitrosamines
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2-0
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3-5 ng/kg body weight
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Many researchers have worked on the biological effects of his N-nitroso
compounds, finding them to be carcinogenic, mutagenic, and teratogenic
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These compounds may
increase the risk of rectal, bladder, colon, pancreatic, and stomach cancer
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Absorption
rates vary with N-nitrosamines
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Most N-nitrosamines are
procarcinogens and undergo metabolic activation
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2
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Hydrolysis of proteinaceous
by-products of edible oil extraction (soybean meal, rapeseed meal, corn gluten, etc
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According to Colin and Peter (2019), the primary chloropropanol identified in HVP
is 3-chloropropane-1,2-diol (3-MCPD) and 2-chloropropane-1,3-diol (2-MCPD) was smaller than
that
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Monochloropropanediol (MCPD) and dichloropropanol (DCP), which are produced from lipids as
well as chloroesters, were intermediates in their synthesis (Colin and Peter 2019)
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During the fermentation process, yeast produced glycerol, which combined
with more chloride during baking to form about 70% of MCPD
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Monoacylglycerols, lysophospholipids, and phosphatidylglycerols have been shown
(along with chloride) to be minor precursors of MCPD in dough
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These chemicals may quantitatively account for the remaining 30% of MCPD in bread
(Colin and Peter 2019)
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Partial acylglycerols (mono- and diacylglycerols) can form these substances due to the
low concentration of chloroesters in bread crumbs at temperatures below 100°C
...

2
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The kidney
was the primary target organ for poisoning in rats and mice, and impacts on male fertility were
also noted
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According to JECFA (2006), the average daily intake of 1,3-DCP
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for the general population was 0
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136 g/kg body weight
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0

Conclusions

Controlling the health effects of Maillard reaction foods, and reaction products is important for
food improvement and development
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A positive contribution of the Maillard reaction is the production of sensory
attributes such as color, taste, aroma and texture
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Numerous toxic compounds
are formed during heating/cooking, some of these compounds have been confirmed to be
mutagenic, carcinogenic, or neurotoxic at high doses
...
However, chemical
changes during heat treatment are very complex phenomena
...
The inclusion of different disciplines and disciplines such as
agronomy, analytical chemistry, food chemistry, food technology, toxicology, epidemiology,
nutrition and consumer research are a very important step
...


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