Dr.
Nguyen Minh Xuan Hong
Food Chemistry
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Dr. NGUYỄN MINH XUÂN HỒNG
Department of Food Biochemistry and Human Nutrition
Faculty of Chemical Engineering and Food Technology
Nong Lam University Ho Chi Minh City
nmxhong@[Link]
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Non-enzymatic browning reaction During preparation and processing of food, the
phenomenon of browning associated with heated and
- Maillard browning reaction stored products occurred.
- Caramelization Non enzymatic browning reaction contribute to the
flavor, color, and aroma of products such as coffee,
Enzymatic browning reaction caramel, bread, and breakfast cereals.
Two major types of nonenzymatic browning;
◦ Caramelization
◦ Maillard browning reaction
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Brown colored products with a typical caramel aroma are
obtained by melting sugar or by heating sugar syrup in the
presence of acidic and/or alkaline catalysts.
Heating of sucrose syrup in a buffered solution enhances
molecular fragmentation and formation of aroma substances
such as dihydrofuranones, cyclopentenolones,
cyclohexenolones and pyrones.
Heating glucose syrup with sulfuric acid in the presence of
ammonia provides intensively colored polymers.
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Mostly thermolysis causes dehydration of the sugar molecule
Commercialize browning products
with introduction of double bonds or formation of anhydro
rings. Introduction of double bonds leads to unsaturated rings
such as furans. Conjugated double bonds absorb light and
Acid fast caramel using ammonium bisulfite
produce color. Often unsaturated rings will condense to (NH4HSO3) as a catalyst; color in soft drink.
polymers yielding useful colors.
Brewer’s color by heating sucrose with
Catalysts increase the reaction rate and are often used to ammonium ion (NH4+); beer products.
direct the reaction to specific types of caramel colors,
solubilities and acidities. Baker’s color by direct heating of sucrose to
get caramel color.
Brown caramel color made by heating a sucrose solution with
ammonium bisulfite is used in cola soft drinks, other acidic
beverages, baked goods, syrups, candies., แยมผลไม้
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Class I: plain, spirit caramel
Class II: caustic sulfite caramel
Class III: ammonia or beer caramel, bakers and
confectioners caramel
Class IV: sulfite–ammonia, soft drink caramel, or
acid proof caramel
The important compound occurred in bread:
Maltol (3-hydroxy-2-methylpyran-4-one),
Isomaltol (3-hydroxy-2-acetylfuran)
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The formation of brown pigments and melanoidin was first The first step in the Maillard browning reaction involves the
observed by French chemists Louis Maillard (1812) condensation between α-amino groups of amino acids or
following the heating of glucose and lysine. proteins and carbonyl groups of reducing sugar. The reducing
Nonenzymatic browning occur between reducing sugar and sugar reacts reversibly with the amine to produce a
free amino acid. glycosylamine.
When aldoses or ketoses are heated in solution with amines, Glycosylamine react via amadori rearrangement to produce
the browning reaction occurred producing numerous 1-amino-2-keto sugar and in case of ketose reverse Amadori
compounds, which are flavors, aromas, and dark colored (Heyns) rearrangement yield 2-amino aldose occurred.
polymeric materials.
The flavors, aromas, and colors may be either desirable or Amadori compounds with different amino acid residues have
undesirable. been detected in many heated and stored foods such as dried
fruit and vegetables, milk products, cocoa beans or soy sauce.
They may be produced by frying, roasting, baking or storage.
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The strecker reactions occur between α- dicarbonyl compounds
Amadori products are only intermediates formed in the course such as deoxyosones and amino acids. The reaction leads to the
of the Maillard reaction. Amadori compounds are degraded to formation of aldehydes, CO2 and α-aminoketones on oxidative
1-, 3-, and 4-deoxydicarbonyl compounds (deoxyosones) in decarboxylation of the α-amino acids.
the pH range 4–7. As reactive α-dicarbonyl compounds, they Strecker aldehydes which are important for their aroma are methional,
yield many secondary products. phenyl acetaldehyde, 3- and 2-methylbutanal, and methyl
propanal. Other compounds which are formed via the Strecker
degradation and influence the aroma of food are hydrogen sulfide
Examples of products obtained on the decomposition of 3- (H2S), ammonia (NH3), 1-pyrroline, and cysteamine.
deoxyosones are 5-hydroxymethylfurfural from hexoses
(HMF) and furfural from pentoses. It occurs in foods at higher concentrations of free amino acids and
under more drastic reaction conditions, at higher temperatures or
under pressure.
Condensation reactions between nucleophilic/electrophilic
The aldehydes, which have one C-atom less than the amino acids,
intermediates of the Maillard reaction result in the formation of
possess a considerable aroma potential, depending on the amino
the colored components, which are called melanoidins. acid degraded.
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Formation of glycoslyamine Formation of Amadori compound
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1-amino-2-keto sugar 16
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Formation of 1,2 Eneaminol
Formation of HMF
Formation of 3-Deoxyosone
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Melanoidins brown pigments, have varying molecular
weights and solubilities in water. Browning is desired in
baking and roasting.
Volatile compounds which are often potent aroma
substances. The Maillard reaction is important for the
desired aroma formation accompanying cooking, baking,
roasting or frying.
Flavoring matter, especially bitter substances, which are
partially desired (coffee) but can also cause an off-taste, in
grilled meat or fish (roasting bitter substances).
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Compounds with highly reductive properties
(reductones) which can contribute to the
stabilization of food against oxidative deterioration.
Losses of essential amino acids (lysine, arginine,
cysteine, methionine).
Compounds with potential mutagenic properties
and compounds that can cause cross-linkage of
proteins.
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pH and Buffers: reaction rate decrease at pH less
than or equal to 6 and high at pH 7.8-9.2 Maintenance of lowest possible temperatures and
avoidance of critical water contents during processing
Temperature: reaction rate increase as temperature and storage.
increase.
Decrease pH.
Sugar structure: D-xylose > L-arabinose > hexoses
(D-galactose, D-mannose, D-glucose, D-fructose) Using sucrose in stead of glucose which is reducing
> disaccharides (maltose, lactose, sucrose) sugar.
Open chain form (free carbonyl) Addition of sulfite such as sulfur dioxide or sulfites.
Rapidly reaction in open chain form
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Prevention of browning reaction by bisulfite
Remove sugar from the food by using yeast or
enzyme (glucose oxidase and catalase).
For examples, dried egg and meat product.
D-ribose oxidase: occur in Lactobacillus
pentoaceticum prevent fish from browning.
Remove protein from the products.
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Enzymatic browning is the process involving
polyphenol oxidase or other enzymes that
create brown color of the products including
fruit and vegetable.
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(phenylalanine ammonia lyase)
polyphenol
oxidase
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