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LIPID IN FOOD

INDUSTRIES

Mansoor Abdul Hamid


Vegetable Oils: Oil Content and Yield Producing
 _________________________________________________________________
 Oil Oil content (%) Oil Yield (pounds/ Acre)
 -----------------------------------------------------------------
 Oilseed
 Canola 40-45 525-590
 Corn 3.1-5.7 215-390
 Cottonseed 18-20 185-210
 Peanut 45-50 1120-1245
 Safflower 30-35 545-635
 Soybean 18-20 400-450
 Sunflower 35-45 460-590
 Tree fuits & kernels;
 Coconut 65-68 650-870
 Olive 15-35 90-260
 Palm 45-50 2670-4450
 Palm kernel 44-53 267-445
__________________________________________
Total consumption : 144,842 mt
Per capita consumption : 13.9 kg/yr
38.0 g/day
The term "lipids" embraces many
different organic substances. In
addition to the triglycerides, this
group also includes, mono and
diglycerides, phosphatides,
sterols, terpenes, fatty alcohols,
fatty acids, fat soluble vitamins,
and other compounds.
Function of F&O in Food product
 new techniques developed over time to
 modify existing vegetable oils and fats so that they can
be made suitable for use in a wider range of
applications in all sorts of food
 • fats give sensory satiety
 • fats are important taste components
 • fats make certain methods of food preparation
possible, such as deep-frying and normal frying
 • fats play a part in the transfer of heat and in the
water activity of a product
 • fats help to determine the consistency, the texture,
the feel in the mouth and the melting behaviour stuffs.
Types of Lipid in Food Industry
1. Animal Fat
 Edible meat fats ~ butter, lard from
pigs, tallow from cattle & sheep, fish oil.
Greatest quantities in temperate
climates and intensive agriculture
2. Vegetables Oil
A) Vegetables oil – Oilseeds ~ major source of oil from
plants
**Seeds – corn, cottonseed, soybean & peanut are
cleaned and tempered – dehulled as needed then flakes
or crushed. Oil is removed by solvent extraction,
application of pressure or their combination.

**The flesh olive pressed for virgin olive oil and; the
residue and kernels are pressed further and/or solvent
extraction for pure olive oil

**Coconut oil is pressed from dried coconut flesh


B) Vegetable shortenings

– made by hydrogenation of refined oils usually


mixtures of soybean and other oils to promote
formations of the desired crystals and extend the range
of plasticity. The oils are treated with H2 with nickel
(catalyst). optional ingredients such as preservatives
and MG-DG emulsifier are added. During rapid
crystallization, agitation and a large amount of air or an
inert gas such as N2 incorporated and finely dispersed.
After packaging, plastic shortenings are tempered for
24-72 hrs; T = 27-32ºC
c) Margarine
– develop to stimulate butter, most frequently are made
from mixtures of vegetable oils that are hydrogenated
to the desired extent. Emulsifiers, vitamin A and
sometimes vitamin D, flavouring and colouring are
added. The aqueous phase containing whey or non-fat
milk solid is cultured, pasteurized and cooled. Salt and
water-soluble preservatives if used are added to this
phase. The two phases are emulsified under controlled
conditions of T and agitation, forming a W-O emulsion
in which the fat conc. ` 80-81%.
3. Specialty Fats
 specialty fats products include cocoa
butter equivalents (CBE), cocoa butter
replacers (CBR), cocoa butter substitutes
(CBS), specially formulated filling fats,
creaming fats, ice-cream fats, milk fat
replacers, shortenings, margarines,
frying fats and many tailor-made fats to
suit customers' requirements. They are
widely used in chocolate coating fats,
chocolates, sugar confectionery, bread,
pastry, cakes, cream filling (for candy,
wafers, biscuits) and coffee whitener
Annual Sales of Deep Fat Fried Foods in U.S.

Food Industries Restaurants


5109 pounds 2109 pounds

$ 15 billion per year


(Snack Food Association, 1997).

Sales of fried foods in U.S. increased by 35% from 1987 to 1996.


-
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
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
Oil Contents in Deep-Fat Fried Foods
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
Chemical Changes of Deep-Fat Frying
• Formation of flavor
• Flavor stability and quality changes
• Color and texture of the fried foods changes
• Nutritional changes
Chemical Reactions in Frying Oil
• Hydrolysis
• Oxidation
• Polymerization
• Pyrolysis
Chemical Reactions in Deep-Fat Frying of Foods

Development of volatile flavor compounds:

- 220 volatile compounds have been identified. Most give


good impacts to food quality and acceptability but for long term
will generated unpleasant flavour (Off flavour ~ rancidity)
Deep-Fat Fried Flavor
4-hydroxy-2-nonenoic acid, lactone
4- hydroxy-3-nonenoic acid
2,4-decadienal
nutty, 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 Acids
Unsaturated acids (cis, trans)
Hydroxy acids

Hydrocarbons – Saturated hydrocarbons


Unsaturated hydrocarbons
Alcohols
Aldehydes - Saturated
Unsaturated
Ketones
Esters
Aromatic Compounds
Lactones
Miscellaneous: 2-Pentyl furan
1,4-Dioxane
Aromatic Compound Formation
CH3 CH CH CH CH C H 2 ( C H 2) n C H3

O2

C H3 CH CH CH CH CH ( C H 2) n C H3
OOH
+ R
- ROH

CH3 CH CH CH CH CH ( C H 2) n C H3
O

+  OR
CH3 CH CH CH CH C ( C H 2) n C H3
O

CH
C (C H2)n C H3
CH
O
CH
C H3
CH

- HO 2

(C H 2) n CH3
Aromatic Compound Formation
C H3 ( C H 2) 3 C H2 C H CH C H2 CH CH ( C H 2) 7 C O O R

O2

C ( C H 2) 7 C O O R

C H2 C H2 ( C H 2)2 C H 3

D - H2 O
C H2 ( C H 2) 6 C O O R

C H2 ( C H 2) 2 C H 3
Formation of -2 Nonelactone
C H3 C H2 C H2 C H2 C H2 CH CH CH2 CH CH R

C H3 C H2 C H2 CH2 C H2 CH CH CH CH CH R

O O H

C H3 C H2 C H2 C H2 C H2 CH CH CH .
CH

+ . OH

C H3 C H2 C H2 C H2 C H2 CH CH CH CH OH
CH CH CH CH CH CH CH CH CH OH
3 2 2 2 2

O
C H3 C H2 C H2 CH2 C H2 CH CH C H2 C
H
-H 
O
C H3 C H2 C H2 C H2 C H2 .
CH CH CH C
H
O2
O

CH CH CH CH CH CH CH CH C.
3 2 2 2 2
OH
+ .OH O

CH CH CH CH CH CH CH CH C OH
3 2 2 2 2
OH
-H O
2

 -2-Nonelactone
Effect of Methionine Analogs on Potato Chip-Flavor
in Deep-Fat Frying.
Compounds Structures Flavor Characteristics

D-Methionine
L-Methionine CH3-S-CH2-CH2-CH(NH2)COOH Good potato chip-like
DL-Methionine

S-Methyl-L-Cysteine CH3-S-CH2-CH(NH2)COOH Good potato chip-like

Obnoxious
Methionine Hydroxy CH3-S-CH2-CH2-CH(OH)COOH (cooked turnip)
Analog

S-Carboxymethyl-L- HOOC-CH2-S-CH2-CH(NH2)COOH Obnoxious


Cysteine (cooked turnip)
Polymer Formation
Carbon-Carbon Bond: A. Vinyl Type

C C

C
Carbon-Carbon Bond: B. Diels Alder Type
H H H H H
C C C C C
- .H

H H H H H
C C C C C
H H H
C C

H H

H H C C H
C C C
H
C C

Intermolecularly or Intramolecularly
Carbon-Oxygen Bond
Through peroxide group – formed by autoxidation.

O
O

This can be formed intermolecularly or intramolecularly.

Through ether linkage – formed at high temperature.

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%

CO O R
CO O R

Noncyclic, Polar C-C Dimer 2.8%


COOR
OH

COOR
OH

Trimers - C-C, 8.4%


Trimers - 2 C-O, or 1 C-C, 1 C-O 4.9%
Diels-Alder Reaction
COOH

COOH

COOH

COOH

COOH

COOH
Dimerization
C H2

CH

C H2

C H2

CH

C H2

Dimerization Between Two Acyl Groups in the Same Triglyceride or


Dimerization Between Two Acyl Groups in Two Triglycerides
Composition of Oxidized and Polymerized Materials Formed
during Simulated Deep-Fat Frying at 185C for 74 Hrs.

TRILINOLEIN TRIOLEIN TRISTEARIN

Cyclic Dimers
Carbon-to-Carbon 4.9 0.0 0.0
Linkages

Noncyclic Dimer
Carbon-to-Carbon 2.8 3.4 0.7
Linkages

Trimers 8.4 0.3 0.4


Two Carbon-to-
Carbon Linkages

Dimers and Trimers


4.9 6.2 1.2
Carbon-to-Carbon or
Oxygen Linkages
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
a
Levels of Linoleic Acid
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 tract


Organ enlargement (kidney & liver)
Growth depression
Carcinogenic properties

Good Practice of Deep-Fat Frying


Fats are not nutritionally damaged.
-
Identify of Sources
• Basic based on physical character – solid or liquid
through appearance but in genera;l source from
animal base more solid compared from vegetable
origins
•Chemical characteristics due to more saturated
fatty acid
•Colour also influence the source of F & O where
short / medium chains of C give whiteness in
colour but longer chain of C more creamy colour
(C4:0 vs C18:0)
• The more saturated the fat, the higher melting
point it is (C18:0 vs C18:1)
•The longer C chains of fatty acid, the higher
melting point it is (C12:0 vs C18:0)

•Status of F & O – fresh, old, good or bad condition

•Quality of F & O – good or bad quality in term of


storage or healthy aspect
Status of Fats and Oils
-
•Status of F & O – fresh, old, good or bad condition

-Fresh samples ~ bright in colour, higher MP, FP, FP


etc, fresh smell and give better flavour of fried
food
-Old samples ~ darker in colour, lower MP, FP, FP
etc, rancit and gave negative contribute to food
-Good ~ higher EFA, higher unsaturated FA
-Bad~ more saturated, Cholesterol
Quality of Fats and Oils
•Quality of F & O – good or bad quality in term of
storage or healthy aspect

- During storage normally oxidation and other


deterioration of F & O, good sample maintain
double bond
- Healthy F & O ~ higher EFA, unsaturated
Thank You…

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