12. deep fat frying chemistry
TRANSCRIPT
CHEMICAL REACTIONS of DEEP-FAT FRYING OF FOODS
Deep-Fat Frying
• Deep-Fat Frying is a process of immersing food in hot oil.
• A process of cooking and drying produces unique fried
foods by simultaneous heat and mass transfer .
• Flavor compounds are formed and retained in a crisp crust
of food
Annual Sales of Deep Fat Fried Foods in U.S.
Food Industries Restaurants
5109 pounds 2109 pounds
$ 15 billion per year
Sales of fried foods in U.S. increased by 35% from 1987 to 1996.
(Snack Food Association, 1997).
Physical and Chemical Reactions during Deep-Fat Frying
Physical Changes of Deep-Fat Frying
• Viscosity Increase
• Thickening of oil
• Decrease of interfacial tension
• Increase of density
• Increase of the specific heat
Products Oil Contents (%)
Potato chips 33-38
Corn chips 30-38
Tortilla chips 23-30
Doughnuts 20-25
Frozen food 10-15
French fries 10-15
Oil Contents in Deep-Fat Fried Foods
• Formation of flavor
• Flavor stability and quality changes
• Color and texture of the fried foods changes
• Nutritional changes
Chemical Changes of Deep-Fat Frying
• Hydrolysis
• Oxidation
• Polymerization
• Pyrolysis
Chemical Reactions in Frying Oil
Chemical Reactions in Deep-Fat Frying of Foods
Volatile Flavor Compounds:
220 volatile compounds have been identified.
Deep-Fat Fried Flavor
4-hydroxy-2-nonenoic acid, lactone4- hydroxy-3-nonenoic acid2,4-decadienalnutty, fried fat notes plus a butter-like note
Some of volatile compounds formed in deep-fat frying condition are known as toxic compounds.
Example:1,4- Dioxane
Benzene Toluene Hexyl-benzene
Volatile Products from Deep-Fat Frying
Acids -- Saturated AcidsUnsaturated acids (cis, trans)Hydroxy acids
Hydrocarbons – Saturated hydrocarbons Unsaturated hydrocarbons
AlcoholsAldehydes - Saturated
UnsaturatedKetonesEstersAromatic CompoundsLactonesMiscellaneous: 2-Pentyl furan
1,4-Dioxane
Aromatic Compound Formation
C H3 C H C H C H C H C H2 (C H2)n C H3
O 2
C H3 C H C H C H C H C H (C H2)n C H3
O O H+ R
- ROH
+ OR
C H3 C H C H C H C H C H (C H2)n C H3
O
C H 3 C H C H C H C H C (C H 2)n C H3
O
CHC H
C (C H2)n C H3
C HC H
O
C H3
(C H 2)n
- H 2O
C H 3
Aromatic Compound Formation
C H3 (C H2)3 C H2 C H C H C H2 C H C H (C H2)7 C O O R
O 2
C H2
C (C H2)7 C O O R
O
C H2 (C H2)2 C H3
C H2
C H2
(C H2)6 C O O R
(C H2)2 C H3
- H O2
Formation of -2 Nonelactone
C H3 C H2 C H2 C H2 C H2 C H C H C H2 C H C H
C H3 C H2 C H2 C H2 C H2 C H C H
C H3 C H2 C H2 C H2 C H2 C H C H
C H3 C H2 C H2 C H 2 C H2 C H C H
.
C H C H C H
O O H
C H C H
C H C H O H
R
R
+ OH.
C H 3 C H2 C H 2 C H 2 C H 2 C H C H C H 2 C
O
H
C H3 C H2 C H2 C H2 C H2 C H
O H
C H
C H 3 C H2 C H 2 C H 2 C H 2 C H C H. CC H
O
H
CC H
O
.
+ .OH
C H3 C H2 C H2 C H2 C H2 C H
O H
C H CC H O H
O
-H 2O
-2-Nonelactone
O2
- H
C H3
C H2
C H2
C H2
C H2
C H C H C H C H O H
Effect of Methionine Analogs on Potato Chip-Flavor in Deep-Fat Frying.
Compounds Structures Flavor Characteristics
D-MethionineL-MethionineDL-Methionine
CH3-S-CH2-CH2-CH(NH2)COOH
Good potato chip-like
S-Methyl-L-Cysteine
CH3-S-CH2-CH(NH2)COOH
Good potato chip-like
Methionine Hydroxy Analog
CH3-S-CH2-CH2-CH(OH)COOH
Obnoxious(cooked turnip)
S-Carboxymethyl-L-Cysteine
HOOC-CH2-S-CH2-CH(NH2)COOH
Obnoxious(cooked turnip)
Polymer Formation
Carbon-Carbon Bond: A. Vinyl Type
C
CC
C
C
B. Diels Alder Type
C C
H
C C C
H H H H
- .H
C
H
H
HHHH
CCCC
C C
H H
C
H
HH
H CC
C
H
C
HC C
Intermolecularly or Intramolecularly
Carbon-Carbon Bond:
Carbon-Oxygen Bond
Through peroxide group – formed by autoxidation.
This can be formed intermolecularly or intramolecularly.
Through ether linkage – formed at high temperature.
O
O
O
O
Polymers Formed during Deep-Fat Frying
The 74 hrs. deep-fat frying conditions
Trilinolenin 26.3% Trilinolein 10.0% Triolein 10.8% Tristearin 4.2%
Types of Polymers
Trilinolein Monocyclic, Nonpolar C-C Dimer 4.9%
Noncyclic, Polar C-C Dimer 2.8%
Trimers - C-C, 8.4%
Trimers - 2 C-O, or 1 C-C, 1 C-O 4.9%
COOR
COOR
COOR
COOR
OH
OH
Diels-Alder Reaction
C O O H
C O O H
C O O H
C O O H
C O O H
C O O H
C H2
C H
C H2
C H2
C H
C H2
Dimerization Between Two Acyl Groups in the Same Triglyceride or
Dimerization Between Two Acyl Groups in Two Triglycerides
Dimerization
Composition of Oxidized and Polymerized Materials Formed during Simulated Deep-Fat Frying at 185C for 74 Hrs.
TRILINOLEIN
TRIOLEIN
TRISTEARIN
Cyclic Dimers Carbon-to-Carbon Linkages 4.9 0.0 0.0
Noncyclic DimerCarbon-to-Carbon Linkages
2.8 3.4 0.7
Trimers Two Carbon-to-Carbon Linkages
8.4 0.3 0.4
4.9 1.2
Dimers and Trimers Carbon-to-Carbon or Oxygen Linkages
6.2
Biological Effects of Used Frying Oil
• A slight depression in growth to very poor growth
• Diminished feed efficiency
• Increased liver, kidney and heart sizes
• Fatty tissues of liver, kidney and heart organs
• Liver enzymes such as thiokinase and succinyldehydrogenase
had lower activity
• The evidence of carcinogenicity (in highly abused frying oil)
Safety
Under Good Practice of Deep-Fat Frying:
Fats are not nutritionally damaged
Frying Oil Analyses by Liquid Chromatography
Thermal Oxidation Effect on Linoleic Acid Concentration
Levels of Linoleic Acida
FAT FRESH OXIDIZED
Corn oil 61.0 1.1
Olive oil 7.7 Trace
Learb 21.7 1.1
Lard 10.7 1.4
a Expressed as % of total fatty acids.
b Lear = Low erucic acid rapeseed oil.
Toxicity Symptoms of Highly Heat-Abused Oils to Laboratory Animals
Irritation of the digestive tractOrgan enlargement (kidney & liver)Growth depression
Carcinogenic properties
Good Practice of Deep-Fat Frying
Fats are not nutritionally damaged.