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CHM2962
Food Chemistry
CHM2962
Food Chemistry
CHM2962
Food Chemistry
Food Chemistry
CHM2962
Food Chemistry
CHM2962
Food Chemistry
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
CHM2962
Food Chemistry
CHM2962
Food Chemistry
CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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Wk1.3 Monosaccharides
Monosaccharides - Structure
Aldoses
Ketoses
CHM2962
Food Chemistry
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Wk1.3 Monosaccharides
Monosaccharides Fischer Projections
D-glucose
CHM2962
Food Chemistry
13
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
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
14
Wk1.3 Monosaccharides
Monosaccharides Chirality: L and D, R and S.
CHM2962
Food Chemistry
15
Wk1.3 Monosaccharides
Monosaccharides Cyclic Structure
CHM2962
Food Chemistry
16
Wk1.3 Monosaccharides
Monosaccharides Mutarotation
Imagine this is the moment immediately prior to cyclisation.
What happens next? Draw the mechanism.
CHM2962
Food Chemistry
17
Wk1.3 Monosaccharides
Monosaccharides - Nomenclature
CHM2962
Food Chemistry
18
Wk1.3 Monosaccharides
Monosaccharides Reducing Sugars
CHM2962
Food Chemistry
19
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:
CHM2962
Food Chemistry
20
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
CHM2962
Food Chemistry
21
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
CHM2962
Food Chemistry
22
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
CHM2962
Food Chemistry
23
Wk1.1 Disaccharides
CHM2962
Food Chemistry
24
Wk1.1 Disaccharides
CHM2962
Food Chemistry
25
Wk1.4 Disaccharides
Disaccharides Invert Sugar :
Golden syrup?
Invertase, an enzyme
Invertase
CHM2962
Food Chemistry
26
Wk1.4 Disaccharides
How do they make this stuff??
CHM2962
Food Chemistry
27
Wk1.5 Oligosaccharides
Oligosaccharides
eg1. Melezitose
eg2. Maltotriose
CHM2962
Food Chemistry
28
Wk1.5 Oligosaccharides
Oligosaccharides
eg3. The galactose+sucrose trisaccharides found in beans:
CHM2962
Food Chemistry
29
In solution:
CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
39
Pyrazines
An example!
CHM2962
Food Chemistry
40
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)
CHM2962
Food Chemistry
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Properties:
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Properties:
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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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Modified Starches:
Chemical transformations can yield new properties:
1. Depolymerisation:
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Modified Starches:
Chemical transformations can yield new properties:
2. Derivitatisation:
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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:
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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.
13
Wk1.1 Polysaccharides!
Why does the pH need to
be in the 2.8-3.3 range?
CHM2962
Food Chemistry
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superjunctions
CHM2962
Food Chemistry
16
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.
CHM2962
Food Chemistry
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CHM2962
Food Chemistry
22
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.
CHM2962
Food Chemistry
23
Wk2a.1 Polysaccharides!
Gums: A couple of examples:
CHM2962
Food Chemistry
24
Wk2a.1 Polysaccharides!
The classic high-fibre breakfast!
CHM2962
Food Chemistry
25
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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2.
3.
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Wk2a: Lipids!
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Fatty Acids:
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Wk2a: Lipids!
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Food Chemistry
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Wk2a: Lipids!
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Glycerol:
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Triglycerides:
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Triglycerides:
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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
CHM2962
Food Chemistry
11
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
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CHM2962
Food Chemistry
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Food Chemistry
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Food Chemistry
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Omega-6, -6
CHM2962
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Wk2a: Lipids!
Fats - Nutrition & Health:
Omega-3, -3
CHM2962
Food Chemistry
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Phospholipids:
Structure:
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Characteristics:
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Wk2a: Lipids!
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Phospholipids: Phosphatidylcholine
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Wk2a: Lipids!
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Phospholipids: Structures
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Phospholipids:
Food Sources
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Phospholipids:
Egg yolk as an emulsifier.
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
10
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CHM2962
Food Chemistry
11
CHM2962
Food Chemistry
12
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CHM2962
Food Chemistry
13
CHM2962
Food Chemistry
14
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CHM2962
Food Chemistry
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CHM2962
Food Chemistry
16
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Food Chemistry
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Food Chemistry
18
CHM2962
Food Chemistry
19
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Food Chemistry
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Food Chemistry
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Food Chemistry
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Food Chemistry
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CHM2962
Food Chemistry
24
CHM2962
Food Chemistry
25
Food Chemistry
26
27
CHM2962
Food Chemistry
28
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
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3
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Wk4: Protein!
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Wk4: Protein!
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5
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Wk4: Protein!
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6
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Protein Quality
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High
Cow's milk
Chicken Egg
Human milk
Beef muscle
Fish
om
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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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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
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*
*
.P
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*
*
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
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10
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Wk4: Protein!
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Denaturation!
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Protein Denaturation
Chemical or physical alteration
of the ordered protein
structure:
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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
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Wk4: Protein!
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CHM2962
15
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
CHM2962
16
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17
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Wk4: Protein!
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CHM2962
18
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Wk4: Protein!
on
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Multi-layer adsorption
Swelling
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Solvation-dispersion (Solution)
CHM2962
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CHM2962
20
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
CHM2962
21
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
CHM2962
22
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)
0.96-1.28
Sodium caseinate
2.95
Calcium caseinate
1.59
Lactic casein
0.97-1.28
Lactalbumin
0.96
CHM2962
23
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CHM2962
24
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
CHM2962
25
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Wk4: Protein!
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Ostwald
.P
Spindle-type viscometer
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Amylograph
to
a
ot
Brookfiled / Haake
used in cereal industry
Rheometers
Bohlin, Carrimed)
CHM2962
26
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CHM2962
27
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.
CHM2962
28
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
CHM2962
29
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
CHM2962
30
Wk4: Protein!
Gelation: (Background Reading):
Important Bonding in Gels
Type
Groups involved
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
CHM2962
31
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Wk4: Protein!
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Protein Analysis:
You will explore the analysis of protein in the lab program:
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CHM2962
32
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
CHM2962
33
CHM2962
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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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CHM2962
3
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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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4
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CHM2962
5
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CHM2962
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CHM2962
8
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CHM2962
9
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11
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CHM2962
12
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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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14
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15
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w
nn
FA
D
to
a
ot
r.c
CHM2962
16
CHM2962
17
Round 1 ^
Round 2 ^
Round 3 ^