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CHM2962 Food Chemistry

Dr. Chris Thompson


Chris.Thompson@monash.edu
Room 135B, 19 Rainforest Walk
Unit Coordinator & Lecturer

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction


What will we be studying?
The chemistry of:
Macronutrients (Carbohydrates, Protein, Fats/Lipids)
Micronutrients (Vitamins, Trace Elements)
Enzymatic & Nonenzymatic Processes
Food emulsions, colloids and surface interactions
Food additives
Pesticides, toxins and residues
Food Case Studies

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction


How are we assessed?
1. Lab Program: Written Reports & Oral Presentations
2. Assignments: Videography and Poster Presentation
3. Final Exam

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction


How are we assessed?
1. Lab Program (20%)
Incl. 10 weeks attendance
Are you:
Group A, B, C or D?
Group E, F, G or H?
Exercises 1-4 (6 weeks)
2-week pracs (Ex 2 & 4)
worth double marks
Pre-labs are compulsory.
The lab component is a
hurdle.
CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction


How are we assessed?
2. Assignments
Poster Presentation (10%)
Due in Week 8 (Groups A, B, C and D)
Due in Week 9 (Groups E, F, G and H)
Info will go onto Moodle in Weeks 5 or 6.
(Topics, format, marking criteria)

Videography (10%)
Includes three training sessions
Week 1 Lecture #3 (11am Thurs) & 2 lab sessions
Final showing and critique in Week 10/11

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction


How are we assessed?
Poster Presentation - (10%)

CHM2962

Food Chemistry

Wk1.1 Food Chemistry Unit Introduction


How are we assessed?
4. Final Exam (60%)

CHM2962

Food Chemistry

Wk1.1 Food Chem. The Macronutrients


What are macronutrients??

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Food Chemistry

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Wk1.2 Definition of Carbohydrates


Definition of Carbohydrates
Name derives from a basic molecular formula Cm(H2O)n
Sometimes m = n

But not always

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Wk1.3 Monosaccharides
Monosaccharides - Structure

Aldoses

Ketoses

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Food Chemistry

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Wk1.3 Monosaccharides
Monosaccharides Fischer Projections

D-glucose
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Wk1.1 Monosaccharides
O

D-Monosaccharide:
A
monosaccharide
that,
when
written as a Fischer projection,
has the OH on its penultimate
carbon to the right

OH
CH2OH

Monosaccharides - Nomenclature
D-Glyceraldehyde
D-Glucose

OH

HO

OH

CH2OH

OH

HO

OH

OH

HO

OH

OH

CH2OH
D-Arabinose

O
H

OH HO

OH

OH

HO

OH

OH

OH

OH

HO

OH

OH

OH

OH

D-Allose

CH2OH
D-Altrose

H
OH

HO

OH

OH

HO

HO

OH

D-Glucose

CH2OH

OH
CH2OH

CHM2962

D-Mannose

D-Gulose

Food Chemistry

HO

HO

OH

OH

CH2OH

CH2OH
D-Xylose

CH2OH

In the case of L-monosaccharide


OH on its penultimate carbon to
the left.

D-Threose

CH2OH
D-Ribose

CH2OH

D-Erythrose

OH
CH2OH
D-Lyxose

HO
H

OH

HO

OH

HO

HO

HO

HO

OH
CH2OH

D-Idose

OH
CH2OH

D-Galactose

OH
CH2OH

D-Talose

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Wk1.3 Monosaccharides
Monosaccharides Chirality: L and D, R and S.

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Food Chemistry

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Wk1.3 Monosaccharides
Monosaccharides Cyclic Structure

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Food Chemistry

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Wk1.3 Monosaccharides
Monosaccharides Mutarotation
Imagine this is the moment immediately prior to cyclisation.
What happens next? Draw the mechanism.

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Food Chemistry

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Wk1.3 Monosaccharides
Monosaccharides - Nomenclature

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Food Chemistry

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Wk1.3 Monosaccharides
Monosaccharides Reducing Sugars

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Food Chemistry

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Wk1.3 Monosaccharides
Monosaccharides Reducing Sugars
How can a ketose act as a reducing sugar, if the requirement
for a reducing sugar is an aldehyde functional group?
Sketch structures to articulate your answer:

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Wk1.4 Disaccharides
Disaccharides eg. Maltose: From malt, the juice of sprouted
barley and other cereal grains.

CH2OH
HO
HO

a-1,4-glycoside bond

CH2OH

OH
O
HO

O
OH

OH

b-maltose because
this -OH is beta
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Wk1.4 Disaccharides
Disaccharides eg. Lactose:
The principle sugar present in milk
About 5% - 8% in human milk, 4% - 5% in cows milk
Hydrolysed by lactase

OH

-1,4-glycoside
OH bond

CH2

HO
OH
D-galactopyranose

O
HO

CH2OH
O
OH
OH
D-glucopyranose
-lactose because
this OH is beta
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Wk1.4 Disaccharides
Disaccharides eg. Sucrose:
Table sugar, obtained from the juice of sugar cane and sugar
beet.
Hydrolysed by invertase

HO
HO

CH2OH
O

-D-glucopyranose

-2,1-glycoside
bond

-1,2-glycoside
bond

OH

OH

O
CH2OH

CH2OH
OH
-D-fructofuranose

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Wk1.1 Disaccharides

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Wk1.1 Disaccharides

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Wk1.4 Disaccharides
Disaccharides Invert Sugar :
Golden syrup?

Invertase, an enzyme

Invertase

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Food Chemistry

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Wk1.4 Disaccharides
How do they make this stuff??

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Food Chemistry

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Wk1.5 Oligosaccharides
Oligosaccharides
eg1. Melezitose

eg2. Maltotriose

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Wk1.5 Oligosaccharides
Oligosaccharides
eg3. The galactose+sucrose trisaccharides found in beans:

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Food Chemistry

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Wk1.5 Properties & Analysis


Physical Properties of Sugars
As a solid:

In solution:

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Food Chemistry

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Wk1.5 Properties & Analysis


Fudge! https://www.youtube.com/watch?v=fXUKYMyqTKU

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Food Chemistry

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Wk1.5 Properties & Analysis


Analysis of Sugars
What methods do you think would be suitable for sugars?

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Food Chemistry

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Wk1.6 Non-Enzymatic Browning Reactions


Browning Rxns of Sugars Caramelisation
Takes place on heating. Temp = ?
Rearrangement g dehydration g further rearrangements

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Wk1.6 Non-Enzymatic Browning Reactions


Browning Rxns of Sugars Caramelisation
Types of products observed with caramelisation:

hydroxyacetyl furan, acrolein, pyrovaldehyde, glyoxal

caramel: acetylformoin & 4-hydroxyl-2,5-dimethylfuran-3-one


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Food Chemistry

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Wk1.6 Non-Enzymatic Browning Reactions


Browning Rxns of Sugars The Malliard Rxn
The mechanism:

CHM2962

Food Chemistry

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Wk1.6 Non-Enzymatic Browning Reactions


Browning Rxns of Sugars The Malliard Rxn
The Amadori product:

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Food Chemistry

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Wk1.6 Non-Enzymatic Browning Reactions


Browning Rxns of Sugars The Malliard Rxn
Which of the three disaccharides discussed earlier (maltose,
lactose, sucrose) can participate in the Maillard reaction?
Justify your answer:

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Wk1.6 Non-Enzymatic Browning Reactions


Browning Rxns of Sugars The Malliard Rxn
The products:

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Wk1.1 Non-Enzymatic Browning Reactions

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Wk1.6 Non-Enzymatic Browning Reactions

Pyrazines
An example!

Imagine the smell


of fresh bread,
biscuits and
cakes!

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Wk2a.1 Polysaccharides!
What are polysaccharides?
High molecular weight polymers, containing many
monosaccharides
Plants:
energy storage (eg starch)
structural skeleton (eg cellulose)
Animals
energy storage (eg glycogen) maintain blood glucose
levels
exoskeleton of arthropods (eg chitin)
Food
starch (digested in human intestine)
cellulose, hemicellulose, pectic compounds (fibre)
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Wk2a.1 Polysaccharides!
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Starch: Two different types:


Amylose (unbranched): 1,4--glycoside bonds
Amylopectin (branched): 1,4--glycoside bonds with 1,6-glycoside bonds ~ every 24-30 glucose units
of

F
PD

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Starch: Amylose (unbranched): 1,4--glycoside bonds


of

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Properties:

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Wk2a.1 Polysaccharides!
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Starch: Amylopectin (branched): 1,4--glycoside bonds with


1,6-- glycoside bonds ~ every 24-30 glucose units
of

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Properties:

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Wk2a.1 Polysaccharides!
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Starch Granules: Size =


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Wk2a.1 Polysaccharides!
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Starch: Gelatinisation
https://www.youtube.com/watch?v=K28l3sJ9Z8g
https://www.youtube.com/watch?v=L6vYxYE1jOg
Forming a starch gel:
~25 oC:
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~50 oC:
~100 oC:
Higher temps:
On cooling:

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Wk2a.1 Polysaccharides!
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Starch: Making Bread


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Starch: Stale Bread


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Wk2a.1 Polysaccharides!
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Modified Starches:
Chemical transformations can yield new properties:
1. Depolymerisation:
of

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Wk2a.1 Polysaccharides!
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Modified Starches:
Chemical transformations can yield new properties:
2. Derivitatisation:
of

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Wk2a.1 Polysaccharides!
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Modified Starches:
Chemical transformations can yield new properties:
3. Crosslinking:
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Wk2a.1 Polysaccharides!
of

Pectins:
F
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Wk2a.1 Polysaccharides!
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Pectins:
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In this depiction of pectins, each straight line represents a galacturonic acid unit.

The double lines, are the occasional rhamnose units.


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Wk1.1 Polysaccharides!
Why does the pH need to
be in the 2.8-3.3 range?

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Wk2a.1 Polysaccharides!
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Seaweed Polysaccharides: Alginates


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-D-mannuronic acid units

-L-guluronic acid units

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Wk2a.1 Polysaccharides!
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Seaweed Polysaccharides: Carageenan


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superjunctions

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Wk2a.1 Polysaccharides!
Dietary Fibre:
The edible parts of plants or
analogous carbohydrates that are
resistant to digestion and
absorption in the human small
intestine with complete or partial
fermentation in the large intestine.
Includes polysaccharides,
oligosaccharides, lignin, and
associated plant substances.
Promote beneficial physiological
effects including laxation, and/or
blood cholesterol attenuation, and/
or blood glucose attenuation.
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Dietary Fibre: -not broken down in the small intestines, but


partially broken down in the large intestine
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Wk2a.1 Polysaccharides!
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Cellulose: An insoluble fibre


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Wk2a.1 Polysaccharides!
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Hemicelluloses: An insoluble fibre


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Wk2a.1 Polysaccharides!
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Hemicellulose or Gum: Oat -glucan


An insoluble fibre?
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Hemicellulose or Gum: Inulin


An insoluble fibre?
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Wk2a.1 Polysaccharides!
Gums: Soluble fibre
Crib Notes: great affinity for water, high viscosity
of their aqueous solutions, will not form gels,
extensive branching, no junction zones (think
polysaccharide gels), capable of trapping large
amounts of water, even quite dilute solutions will
be viscous.
Thickening agents, emulsions.

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Wk2a.1 Polysaccharides!
Gums: A couple of examples:

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Wk2a.1 Polysaccharides!
The classic high-fibre breakfast!

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Wk2a: Lipids!
Learning Objectives:
Identify classes of lipids and fatty acids
Explore different reaction of fats:
Oxidative and hydrolytic rancidity
Investigate fats as components of food
Discuss analysis method for lipids

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Wk2a: Lipids!
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Three Roles of Lipids in Human Biology:


1.
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2.

3.

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Wk2a: Lipids!
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Lipids, Fats and Oils. Whats the difference?


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Wk2a: Lipids!
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Fatty Acids:
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Wk2a: Lipids!
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Fatty Acids - Saturated:


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Wk2a: Lipids!
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Fatty Acids - Unsaturated:


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Wk2a: Lipids!
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Fatty Acids - Nomenclature:


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Wk2a: Lipids!
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Glycerol:
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Wk2a: Lipids!
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Triglycerides:
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Wk2a: Lipids!
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Triglycerides:
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Food Chemistry

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Wk2a: Lipids!
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Total Fat Content:


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Wholemeal flour
White bread
Madiera cake
Flaky pastry
Skimmed milk
Whole milk
Human milk
Soya milk
Clotted cream
Cheese brie
Cheese cheddar
Dairy ice cream
Egg yolk
Egg white
Butter
margarine
shortbread

Lard
Vegetable oil
Bacon streaky, fried
Pork sausage , grilled
Beef roast
Lamb chop , grilled
Roast chicken
Turkey breast,roast
Raw cod
Battered cod
Smoked mackerel
Taramasalata
Brazil nuts
Peanuts, dry roast
Plain chocolate
Milk chocolate

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Wk2a: Lipids!
Fats - Nutrition & Health:
Role much more complicated than previously thought.
Fat is an essential macro-nutrient.
High levels of saturated fats are bad
Mono-unsaturated fats now being recommended in lieu of
carbohydrate!
Eg. The LCHF diet

CHM2962
Food Chemistry

12

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Wk2a: Lipids!
on
si

The Essential Fatty Acids:


of

F
PD
r-

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.P

w
w

w
nn

FA

D
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r.c

CHM2962
Food Chemistry

Thinkstock

13

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Wk2a: Lipids!
on
si

The Essential Fatty Acids:


of

F
PD
r-

o
at

t
no

An
.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

Thinkstock

14

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Wk2a: Lipids!
on
si

trans Fatty Acids:


of

F
PD
r-

o
at

t
no

An
.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

Thinkstock

15

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Wk2a: Lipids!
on
si

trans Fatty Acids:


of

F
PD
r-

o
at

t
no

An
.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

Thinkstock

16

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Wk2a: Lipids!
on
si

Fats - Nutrition & Health:


Omega-3, -3
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

Omega-6, -6

CHM2962
Food Chemistry

Thinkstock

17

Wk2a: Lipids!
Fats - Nutrition & Health:
Omega-3, -3

CHM2962
Food Chemistry

Thinkstock

18

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Wk2a: Lipids!
on
si

Fats - Nutrition & Health:


The ratio of -6/-3 fats appears to be important
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
r.c

om

The role of polyunsaturated fats is now


not clear:
High -6/-3 ratio appears to
promotes oxidation of cholesterol,
which leads to atherosclerotic
plaque
Trans polyunsaturated fatty acids appear
to be bad.
CHM2962
Food Chemistry

Thinkstock

19

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Wk2a: Lipids!
on
si

Phospholipids:
Structure:
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

Characteristics:

CHM2962
Food Chemistry

20

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Wk2a: Lipids!
on
si

Phospholipids: Phosphatidylcholine
of

F
PD
r-

o
at

t
no

An
.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

21

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Wk2a: Lipids!
on
si

Phospholipids: Structures
of

F
PD
r-

o
at

t
no

An
.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

22

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Wk2a: Lipids!
on
si

Phospholipids:
Food Sources
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

23

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Wk2a: Lipids!
on
si

Phospholipids:
Egg yolk as an emulsifier.
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

24

Wk3: Lipids Part 2!


Learning Objectives:
Identify classes of lipids and fatty acids
Explore several reaction of fats:
Saponification
Oxidative and hydrolytic rancidity
Investigate fats as components of food
Discuss analysis method for lipids

CHM2962
Food Chemistry

Wk3: Lipids Part 2!


Reactions of Fatty Acids and Triglycerides:
1. Esterification
2. Hydrogenation
3. Hydrolysis & Saponifaction
4. Reactions leading to rancidity:
i. Chemical Hydroylsis
ii. Enzymatic Hydroylsis
iii. Oxidation

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Hydrolysis & Saponifaction
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Hydrolysis & Saponifaction
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Hydrolysis & Saponifaction
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity:
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Chemical Hydrolysis
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Enzymatic Hydrolysis
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation
of

F
PD

r-

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at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation: Initiation.
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

10

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation: Propagation.
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

11

Wk3: Lipids Part 2!


Reactions of Fatty Acids and Triglycerides:
Rancidity via Oxidation: Propagation.

CHM2962
Food Chemistry

12

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation: Termination.
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

13

Wk3: Lipids Part 2!


Reactions of Fatty Acids and Triglycerides:
Rancidity via Oxidation: Testing for rancidity.

CHM2962
Food Chemistry

14

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation: Catalysts for Food Oxidation.
of

F
PD

r-

o
at

t
no

An

.P

w
w

Free metal cations (Mx+): Transition metal cations, essential


minerals
Dissociated heme: Porphyrin with a central metal cation, Mx+
Intact heme proteins: Enzymes (peroxidase, catalase),
oxygen binding proteins (hemoglobin, myoglobin),
chlorophyll, cytochromes
Nonheme metaloproteins: Lipoxygenase, superoxide
dismutase
Organic reducing agents: Ascorbic acid, glutathione
Sensitizers: Dyes, fluorescent compounds
nn

FA

to

a
ot

om

r.c

CHM2962
Food Chemistry

15

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation: Warmed-over Foods (WOF).
Charateristics:
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

16

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Rancidity via Oxidation: Warmed-over Foods (WOF).
Prevention:
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

17

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Analysing Lipid Oxidation: Peroxide Value via potentiometry
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

18

Wk3: Lipids Part 2!


Reactions of Fatty Acids and Triglycerides:
Analysing Lipid Oxidation: Peroxide Value via colorimetry

CHM2962
Food Chemistry

19

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Analysing Lipid Oxidation: Thiobarbituric acid
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

20

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Wk3: Lipids Part 2!


on
si

Reactions of Fatty Acids and Triglycerides:


Analysing Lipid Oxidation: Other Methods
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

21

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Wk3: Lipids Part 2!


on
si

Physical Properties of Fats & Oils


Melting Point
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

22

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Wk3: Lipids Part 2!


on
si

Physical Properties of Fats & Oils


Smoke Point
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

23

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Wk3: Lipids Part 2!


on
si

Physical Properties of Fats & Oils


Texture
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
Food Chemistry

24

Wk3: Lipids Part 2!


Food Applications of Fats & Oils: Frying
Deep-fried foods
Short shelf life products donuts, fried fish or fried
chicken (high moisture content)
Several months shelf life potato chips, fried snack
products (low moisture content)
Food is exposed to hot oil (180-190C, minimum 163C) in
the presence of atmospheric oxygen
The oil completely surrounds the raw food.
Alters the quality, appearance, flavor & odor

CHM2962
Food Chemistry

25

Wk3: Lipids Part 2!


Food Applications of Fats & Oils
Frying:
Destroys microorganisms &
enzymes.
Fast to prepare.
Two main functions of oil in
deep-fat fried foods
Conducts heat
Oil becomes part of the foods
(interact with proteins, lipids &
CHO) producing flavours,
colours and odours
CHM2962

Food Chemistry

26

Wk3: Lipids Part 2!


Food Applications of Fats & Oils: Frying
>196C
Rapid degradation of fat
Uneven cooking burnt surface & undercooked interior
Oil temperature should be higher than food
Upon immersion, food surface T increases quickly, small
H2O bubbles evolve as the surface moisture is vaporized
Internal H2O travels to the food surface
Crust begins to form on food surface
Crust has a porous structure with different sized capillaries
in which hot oil will replace the H2O
CHM2962
Food Chemistry

27

Wk3: Lipids Part 2!


Food Applications of Fats & Oils: Frying
Getting the temperature right!
When heat differential between oil & food is too great
the product overcooked outside & undercooked inside
When heat differential is too low oil will penetrate the
food resulting soggy greasy foods
If the pressure inside a food decreases oil seeps into the
food, creating soggy, greasy foods

CHM2962
Food Chemistry

28

Wk3: Lipids Part 2!


Food Applications of Fats & Oils: Frying
At high temperature, oxidation conditions are
enhanced!
Fried in the presence of O2.
Increase in temp, increase in kinetics.
Food contain minerals (catalysts)
Some of these oxidation products add to the
flavour
Many are bad - aldehydes, ketones,
hydrocarbons, lactones, alcohols, esters,
acids, free fatty acids, polymeric compounds
CHM2962
Food Chemistry

29

Wk4: Protein!
Learning Objectives:
Identify the important sources of protein in the human diet.
Discuss the relationship between molecular structure and
important food properties such as solubility, water
absorption, heat stability, viscosity, gelation, emulsification,
foaming & flavour binding
Investigate the protein chemistry of several important foods
such as dairy, egg, meat and bread.

CHM2962
1

Wk4: Protein!
Amazing Proteins:
Unlike the polysaccharides there cannot be anything vague
about the exact length of the chain. If even one amino acid in
the sequence is wrong then it is quite likely that the protein will
lose its biological activity. It is the sequences of the amino acids
in proteins that are defined by the sequences of bases in the
DNA that makes up our genes.
- Coultate, p126
Eg. Casein, from milk

CHM2962
2

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Wk4: Protein!
on
si

The role of proteins in living systems:


of

F
PD
r-

o
at

t
no

An
.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
3

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Pr

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Wk4: Protein!
of

F
PD

r-

o
at

t
no

An

Heading
Text

.P

w
w

nn

FA

to

a
ot

om

r.c

CHM2962

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Wk4: Protein!
on
si

Essential Amino Acids & Protein Quality


Why essential?
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
5

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Wk4: Protein!
on
si

Essential Amino Acids & Protein Quality


Chemical Score
of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
6

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Wk4: Protein!
on
si

Essential Amino Acids & Protein Quality


Chemical Score
of

F
PD

r-

o
at

t
no

An

.P

w
w

Protein Quality
nn

FA

D
to

a
ot

High
Cow's milk
Chicken Egg
Human milk
Beef muscle
Fish

om

r.c

Intermediate
Soy flour
Sunflower seed
Rice
Potato
Oats

Low
Peas
Cornmeal
White flour
Cassava
Gelatin

CHM2962
7

Wk4: Protein!
Dietary Protein: Where does it come from?
Traditional:
Animal: Meat, dairy, fish, egg.
Vegetable: soy, wheat, legume.
Newer Types of Protein Products
Protein hydrolysates & Bioactive peptides
Casein/whey/wheat/soy/fish hydrolysates
Casein macropeptide
Microalgal protein source
Spirulina
CHM2962
8

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Wk4: Protein!
on
si

Dietary Protein: Where does it come from?


of

F
PD
An

r-

o
at

t
no

nn

FA

to

Wholemeal bread
White bread
Milk chocolate
Tofu steamed
Cornflakes
Frozen peas
Yoghurt
Potato crisps
Baked beans canned
Plain chocolate
Pasta
Ice cream
Cows milk
Soya milk

om

r.c

*
*

.P

w
w

*
*

Almonds
Lean raw lamb
Chicken raw
Lean raw beef
Brie cheese
Cod fillet raw
Beefburgers raw
Whole egg
Pork sausage raw

39.4
27.5
25.5
25.5
24.3
21.1
20.8
20.5
20.3
19.3
17.4
15.2
12.5
10.6

a
ot

cheese
* Parmesan
canned
* Tuna
cheese
* Cheddar
peanuts
* Dry
Dried lentils

9.2
8.4
8.4
8.1
7.9
6.0
5.7
5.6
5.2
4.7
3.6
3.6
3.2
2.9

Raw beansprouts
Canned sweetcorn
Rice
Raisins
Raw mushroom
Potatoes new
Raw cabbage
Human milk
Runner beans cooked
Bananas
Jam
Raw apples
Beer
Stout

2.9
2.9
2.6
2.1
1.8
1.7
1.7
1.3
1.2
1.2
0.6
0.4
0.3
0.3

CHM2962
9

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Wk4: Protein!
on
si

Protein Functionality in Food:

of

F
PD

r-

o
at

t
no

An

.P

w
w

w
nn

FA

D
to

a
ot
om

r.c

CHM2962
10

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Wk4: Protein!
on
si

Protein Functionality in Food:


All relates back to molecular structure:
of

F
PD

r-

o
at

t
no

An

.P

w
w

Amino acid composition and sequence


Size & Shape
Conformation secondary, tertiary and
quaternary
Charge and their distribution
Hydrophobicity/hydrophilicity ratio
Rigidity / flexibility (inter and intra
polypeptide linkages)
nn

FA

to

a
ot

om

r.c

Denaturation!
CHM2962
11

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Wk4: Protein!
on
si

Protein Denaturation
Chemical or physical alteration
of the ordered protein
structure:
of

F
PD

r-

o
at

t
no

An

.P

w
w

nn

FA

D
to

a
ot
om

r.c

Consequences
Altered water binding capacity
Decreased solubility (due to exposure of hydrophobic
groups)
Loss of biological activity
Increased intrinsic viscosity
Changes gelation and surface properties etc.
CHM2962
12

Wk4: Protein!
Physical Functionality of Protein Ingredients:
1. Solubility
2. Water Absorption
3. Heat Stability
4. Viscosity
5. Gelation
6. Emulsification & Foaming
7. Flavour binding

CHM2962
13

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Wk4: Protein!
on
si

Physical Functionality of Protein Ingredients:


1. Solubility: Pre-requisite for most other desired properties.
Dependent on pH, (eg casein pH 4.6)
2. Water Absorption: Ability to bind water and swell. Waterprotein interactions through peptide bonds (dipole-dipole /
H-bond) or side chains (polar, non-polar, ionic)
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Physical Functionality of Protein Ingredients:


3. Heat Stability: Ability to withstand heat without thickening.
Essential attribute in many food product applications
4. Viscosity: Related to hydration properties
5. Gelation: Ability to form a gel network
6. Emulsification & Foaming: Ability to stabilise interfaces.
Proteins move to interface and get adsorbed.
7. Flavour binding: Ability to carry flavours
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Wk4: Protein!
Physical Functionality of Protein Ingredients:
Protein

Emulsifying

Whipping

Gelation

Film
Formation

Stability

Egg white

low

high

high

medium

unstable to heat

Egg yolk

high

low

medium

low

unstable to heat

Caseinate

high

medium

low

high

heat stable,
unstable to acid

Whey protein
isolate

medium

low - high

low - high

medium

acid stable,
unstable to heat

Soy protein
isolate

medium to
high

low to
medium

medium

medium high

unstable to heat
and acid

Fish protein
isolate

medium

high medium

low-medium

unstable to heat

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Wk4: Protein!
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Hydration & Solubility of Proteins (Background reading):


Hydration Depends on the balance between protein-solvent
(hydrophilic) and protein-protein (hydrophobic) interactions
Empirical relationship:
Proteins with lower hydrophobicity and higher charge
density have higher solubility for most proteins
Exceptions occur myoglobin (charge frequency 0.34,
hydrophobicity 1090 cal/mole) is less soluble than serum
albumin (charge frequency 0.33, hydrophobicity 1120 cal/
mole)
Suggests importance of physical and chemical properties
of the protein surface (which is influenced by protein
folding) rather than average charge frequency or
hydrophobicity
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Wk4: Protein!
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Hydration & Solubility of Proteins (Background reading):


Hydration important for 3-D structure and functionality of
proteins
Without water proteins lack activity
Proteins have conformational flexibility
Possess a wide range of hydration states
Proteins interact with water through peptide bonds (dipoledipole or H-bond, bridges can be formed C=O and NH
protons) or through amino acid side chains (interactions
with ionised, polar or non-polar groups)
Presence of accessible water causes loosening of protein
structure
Water acts as a plasticiser influences internal motions in
proteins
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Hydration & Solubility of Proteins (Background reading):


Dry protein

Water molecule adsorption via polar binding

Multi-layer adsorption

Liquid water condensation

Swelling
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Solvation-dispersion (Solution)

Swollen insoluble Mass

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Hydration & Solubility of Proteins (Background reading):


Influenced by pH, temperature, time of hydration, ionic
strength and presence of other components
Changes in pH Affect ionisation of side chains and net
charge Affect water holding (Minimal hydration at pI due to
maximum protein-protein interaction)
temperature generally water holding BUT there are
exceptions depending on how temperature affects
conformation
Ionic strength - Ionic salts affect water interaction with
proteins by disrupting electrostatic and hydrophobic
interactions and influence conformational stability of proteins
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Wk4: Protein!
Hydration & Solubility of Proteins (Background reading):
Hydration in Air:
When dry proteins are exposed to air of high water content
they rapidly bind water up to a maximum quantity, which
differs for different proteins.
Usually it is 10 to 20 percent of the weight of the protein.
The hydrophilic groups of a protein are chiefly:
the positively charged groups in the side chains of lysine and
arginine
the negatively charged groups of aspartic and glutamic acid
Hydration may also occur at:
the hydroxyl (OH) groups of serine and threonine
the amide (CONH2) groups of asparagine and glutamine
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Wk4: Protein!
Hydration & Solubility of Proteins (Background reading):
Hydration in Water:
In aqueous solution proteins bind some of the water
molecules very firmly
Others are either very loosely bound or form islands of water
molecules between loops of folded peptide chains
Water molecules may also form bridges between the C=O
and NH groups of adjacent peptide chains
formation of sheets
Amount of water bound varies
globular: 1 g has 0.3 to 0.5 g water
elongated peptides: 1 g has 25 to 30 g

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Wk4: Protein!
Hydration & Solubility of Proteins (Background reading):
Measuring protein hydration:
Definition: Mass of water associated with or occluded by 1 g
(dry weight) of protein
Product

(g H20/g)

Skim milk powder

0.96-1.28

Sodium caseinate

2.95

Calcium caseinate

1.59

Lactic casein

0.97-1.28

Lactalbumin

0.96
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Viscosity (Background Reading):


Definition: Viscosity of a fluid is its resistance to flow
Depends on intrinsic properties of the protein
MW
size,
volume
structure
charge
ease of deformation
Protein-solvent interactions (swelling, solubility,
hydrodynamic hydration sphere.)
Protein-protein interactions (size of aggregates)
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Wk4: Protein!
Viscosity (Background Reading):
Definition:Viscosity of a fluid is its resistance to flow
Affects consistency of foods
eg stirred yoghurt, milk shake, tomato sauce
Affects processing characteristics
eg during pumping, heating, cooling, spray drying
(eg chocolate mass viscosity more work required in
the system with high viscosity chocolate mass)
Factors that affect Viscosity
pH
Temperature
Concentration
ionic strength
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Viscosity (Background Reading):


Measuring Viscosity
Flow-type viscometer
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Ostwald

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Spindle-type viscometer
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Amylograph

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Brookfiled / Haake
used in cereal industry

Rheometers
Bohlin, Carrimed)

(Note: Conditions of testing can


influence result)

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Gelation: (Background Reading):


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Definition: Gels are formed when a viscous fluid is changed into


a 3-D network with viscoelastic characteristics
(Proteins are polymerised due to favourable protein-protein
interactions)
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Why is gelation important?


Affects structure and texture of foods
Eg set yoghurt, cheese, hard boiled eggs, tofu, re-formed
meat products

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Wk4: Protein!
Gelation: (Background Reading):
Transformation of protein from a sol to a gel-like structure
Linked to ability of proteins to dissociate / denaturation
Depends on molecular properties of proteins (irreversible gel
or soluble aggregated formed depending on levels of various
amino acids)
Mechanism
Formation of a molecular network.
Entrapment of water in the network via H-bonds.
Immobilisation of water, creating the gel.

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Wk4: Protein!
Gelation: (Background Reading):
Step 1 Change in conformation (usually heat-induced) or
partial denaturation of protein molecules; viscosity increases
due to an increase in the molecular dimensions of unfolding
proteins
Step 2 Gradual association or aggregation of individual
denatured proteins; exponential increase in viscosity as
material approaches a continuous network

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Wk4: Protein!
Gelation: (Background Reading):
Factors Affecting Gel Formation:
Temperature
Depends on type of protein and conditions for gelation
Heating induces unfolding of proteins which leads to non-native
conformation and hence altered gelling properties (eg egg-white gels)
Cooling can also cause formation of protein gels (eg gelatin)

Protein concentration
pH
Salt concentration
through their effects on conformation of and charge of proteins, affect
gelation

Calcium concentration
Free sulfhydryl concentration
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Wk4: Protein!
Gelation: (Background Reading):
Important Bonding in Gels
Type

Energy (kJ/mole) Interaction


distance
Angstroms

Groups involved

Role in gel matrix

Covalent

330-380

1-2

-S-S-

Bridging, ordering

Hydrogen

8-40

2-3

-NH.O=C-OH.O=C-

Bridging, stabilising

Hydrophobic

4-12

3-5

Non specific

Strand thickening,
strengthening,
stabilising

Ionic

42-84

2-3

-NH3+
-COO-

Solvent interactions,
salt links

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Protein Analysis:
You will explore the analysis of protein in the lab program:
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Exercise 2: The Kjeldahl Method, Gravimetric Analysis And


Infrared Spectroscopy
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Exercise 3: Assaying Protein Concentration & Ph Dependence


Of Protein Solubility

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Wk4: Protein!
Protein Analysis:
Other Methods:
Sedimentation / ultracentrifugation
Chromatograhpy
Electrophoresis
Light scattering / neutron scattering
Spectroscopy UV, fluorescence, IR and Raman, NMR, CD
X-ray
Microscopy EM, SEM, confocal
Mass spectrometry electronspray ionisation and MALDITOF
Thermal analysis - DSC

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Wk4: Protein Part 2


Learning Objectives:
Identify the important sources of protein in the human diet.
Discuss the relationship between molecular structure and
important food properties such as solubility, water
absorption, heat stability, viscosity, gelation, emulsification,
foaming & flavour binding
Investigate the protein chemistry of several important foods
such as dairy, egg, meat and bread.

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Wk4: Protein Part 2


Protein Functionality in Food:
All relates back to molecular structure:
Amino acid composition and sequence
Size & Shape
Conformation secondary, tertiary and
quaternary
Charge and their distribution
Hydrophobicity/hydrophilicity ratio
Rigidity / flexibility (inter and intra
polypeptide linkages)
Denaturation!
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Bovine Protein:
Bos Taurus
Aqueous source of protein!
Particularly important for children
Also: lactose, minerals, vitamins, fats.
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Bovine Protein:
Drop pH to 4.6, and milk separates into curds
and whey
~80% casein proteins
~20% whey proteins
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Bovine Protein - Casein:


aS-casein (mass ~ 2.35 x 104)
b-casein (mass ~ 2.40 x 104)
All present in milk
k-casein (mass ~ 1.90 x 104)
g-casein
Generated upon processing of milk
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aS-casein primary structure:

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Bovine Protein Casein:


25-30 casein molecules form a
sub-micelle.
Hydrophobic components
inside.
Hydrophilic components on
the surface.
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Many (~103 - 104) submicelles units aggregate to


form a micelle.
Roughly spherical
~600 nm diameter
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Bovine Protein Casein:


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Bovine Protein Hard Cheeses (eg. Cheddar, stilton):


Rennet, prepared from the chymosin enzyme, extracted
from the cows fourth stomach.
Enzyme cleaves here:
Amine (hydrophobic) end stays in the curd.
Acidic (hydrophilic) solubilises into the whey, discarded.
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k-casein primary structure:

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Egg Whites Fried Eggs:


11%-13% protein, the rest is water
Ovalbumin has phosphate groups (a bit like a & b-casein)
Readily denaturated upon heating.
(Think rapid onset of the white rigid gel when frying eggs!)
Due to the unfolding of the protein, enabling new sulfhydryl
bridges R-S-S-R
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Egg Whites Meringues, Foams & Emulsions:


Air can disrupt the micelle structure of the protein.
Expose hydrophobic parts of the protein.
A denatured film can form around air or fat bubbles
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Air g formation of a foam!


Fat g an emulsion!
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Meringue: Must get sufficient air


through the egg whites.
Too much beating denatures the
protein so much it can no longer
hold water, and the foam collapses.
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Egg Whites Meringues, Foams & Emulsions:


Why might it be important to prepare foams and
emulsions at a pH where the proteins are close to their
isoelectric point?
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Protein from Meat:


Protein source from muscle tissue.
Protein also on bones, and the skin.
50-80% water
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Gelatin:
Bones crushed up.
Steeped in HCl (aq) to dissolve
calcium phosphate.
Treated with lime, Ca(OH)2, to
break down the collagen
chains.
Lime is washed away, also
removing any fats.
Hot water then dissolves the
soluble proteins, which form the
gelatin.
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Protein from Bread:


Specifically, from wheat:
Endosperm store of nutrients for the
plant.
Endosperm cells consist of starch granules
in a matrix of protein.
Wheat flour is about 7-15% protein.
~15% protein soluble mostly enzymes
~85% protein insoluble (@ neutral pH)
gluten
~1/6 polar amino acid residues
compared to casein
High % glutamine and proline (Ncontaining sidechains.)
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Protein from Bread:


Specifically, from wheat:
~50% gluten comprised of gliadins
Can be extracted by ethanol
Remainder is the glutenins, less
soluble.
A single variety of wheat may have
many many different types of gliadin
protein molecules.
However, there are common
structural features, resulting in
common secondary structures:
Eg b-spirals
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Protein from Bread:


Kneading the dough.
Breaks down starch in
glucose, reacts with yeast to
form CO2.
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Also important for the protein!


Breaks the H-bonds in the
gliadins and glutenins.
New H-bonds are forms as
proteins rearrange, creating a
structure which is able to trap
gases as the bread bakes.
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Wk4: Protein Part 2


Food Chem Quiz Night: 1pm Thurs (Exam Revision!)
Form your teams, and seat yourselves in S6.

CHM2962
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Questions to quiz night

Answers to quiz night

Round 1 ^

Round 2 ^

Round 3 ^