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F1 Food Groups
Food Any substance, processes, partially processed, or raw that is intended
for human consumption. Includes drink, gum, and any substance which
has been used in the manufacture, preparation or treatment of food
but does not include cosmetics, tobacco, or substances used only as
drugs
Nutrients Any substance obtained from food and used by the body to
provide energy, regulate growth, maintenance and repair of the
bodys tissues. Include: Carbohydrates, Proteins, Lipids,
Vitamins, Minerals, and Water
1. Carbohydrates
Have empirical formula: CH2O
Simplest carbohydrates are monosaccharides
Monosaccharides contain: 1 carbonyl (C=O), at least 2 OH groups
(for polymerization), and 3-6 carbons (to make a ring)
Monosaccharides w/ formula C5H10O5 are known as pentoses (ribose)
Monosaccharides w/ formula C6H12O6 are known as hexoses (glucose)
Ex.
Glucose
(monosacc)
Fructose
(monosacc)
yields
Sucrose
(dissacharide)
2. Proteins
are polymers made up of chains of 2-amino acids
amino acids have general formula H2NCHRCOOH where R is the side
chain which may be the same or different from other R groups
Ex. H2N-CH-C-OH
H-N-CH-C-OH
H-N-CH-C-OH
H2N-CH-C--N-CH-C--N-CH-C-OH
Amide Link
(Peptide Bond)
+ 2H2O
H2C-O-C-R1
H2C-O-C-R2
H2C-O-C-R3
The R Group
R group determines physical & chemical properties of the lipid
Typically 15-25 carbon atoms long
A) Fats
Fats are solid at RT (butter, lard, shortening)
R groups contain only saturated carbons (do not have C=C double bonds)
B) Oils
Oils are liquid at RT
R Groups contain at least 1 C=C double bond
Mono-unsaturated lipids have 1 C=C double bond
(olive oil, canola oil, peanut oil)
Polyunsaturated lipids have more than 1 C=C
(sunflower oil, fish oil)
Name
Saturated Fatty Acids
Lauric Acid CH3(CH2)10COOH
Myristic Acid CH3(CH2)12COOH
Palmitidc Acid CH3(CH2)14COOH
Stearic Acid CH3(CH2)16COOH
Unsaturated Fatty Acids
Oleic Acid CH3(CH2)7CH=CH(CH2)7COOH
Linoleic Acid
CH3(CH2)4CH=CHCHCH2=CH(CH2)7COOH
#of C
atoms/
molec
# of
C=C
bonds
M.P.
(C)
12
14
16
18
0
0
0
0
44.2
54.1
62.7
69.6
18
10.5
18
-5.0
trans,trans-linoleic acid
Stearic Acid
18 carbons
no C=C bonds
mp = 69.6C
Linoleic Acid
18 carbons
2 C=C bonds
mp = -5.0C
C=C
unsaturated
H2
C-C
saturated
Advantages of saturation:
Increases mp, hardness, and chemical stability by making them less
susceptible to oxidation
Margarine is manufactured this way
Disadvantages of saturation:
Oils that contain only cis-fatty acids may undergo partial hydrogenation
to produce trans-fatty acids
Trans-fatty acids behave more like saturated fats which are high in
cholesterol, harder to metabolize and excrete, therefore accumulate as
fatty tissue. They are also a lower quality energy source
F3 Shelf Life
a food reaches its shelf life when it no longer maintains the expected
quality due to changes in flavour, smell, texture, and appearance, or
because of microbial spoilage
2) Change in pH
causes changes in flavour (sour w/ low pH), colour, browning, and loss of
nutrients
3) Light Exposure
4) Temperature
5) Exposure to Air
hydrolysis of the triester (w/ water) by breaking down a lipid into its
component propane triol and its fatty acids
reverse of esterification where water is added
takes place more rapidly in the presence of enzymes (lipase), heat and
moisture
deep frying (high temp) increases rate of hydrolysis
H2C-O-C-R1
H2C-O-C-R2
H2C-O-C-R3
Lipid
(polyester)
H2C-OH
+ 3H2O
H2C-OH
HO-C-R1
+
H2C-OH
HO-C-R2
HO-C-R3
B) Oxidative Rancidity
R-O-O
peroxide radical
R-O-O + H-R
R-O-O-H + R
hydroperoxide
Termination
B) Processing
C) Additives
F4 Colour
The Colour Wheel
Pigment
Carotenoids
The most widespread pigment in nature
Large majority produced by algae.
Act as a precursor for vitamin A.
Colours range from yellow to orange to red, including bananas, carrots,
tomatoes, watermelon, red/yellow peppers and saffron
Red astaxanthin, when present as a complex with protein, gives the blue
or green hue found in live lobsters and crabs and pink colours of salmon.
3) Chlorophyll
The major light-harvesting pigments for photosynthesis found in green
plants.
4) Haem
The red pigment found in red blood cells and muscle tissue.
* Myoglobin is responsible for the purplish-red colour of meat.
(B)
carbinol base
(colourless)
(C)
chalcone
(colourless)
They form deeply coloured coordination complexes with Fe3+ and Al3+
ions, a source of which can be the metal cans to which the fruit is
exposed; this causes a discolorations in canned fruit. They become less
stable when exposed to heat, causing a loss of colour and browning.
2) Carotenoids
The presence of multiple unsaturated carbon-carbon double bonds
makes carotenoids susceptible to oxidation catalysed by lights, metals
and hydroperoxides. Oxidation results in the bleaching of colour, loss
of vitamin A activity and off odours.
They are stable up to 50C and in the pH range of 2-7, and,
therefore, are not degraded by most forms of processing. With
heating, the naturally occurring trans isomer rearranges to the cis
isomer.
3) Chlorophyll
Reaction with heat depends on pH. In a basic solution (pH 9),
chlorophyll is stable, and in an acidic solution (pH3) it is unstable.
When heated, the cell membrane of the plant deteriorates, releasing
acids, which decrease the pH. This results in the magnesium atom
being displaced by two hydrogen ions, resulting in the formation of
olive-brown pheophytin complex. This cell degradation during heating
also makes the chlorophyll more susceptible to photo-degradation.
4) Haem
During oxidation, oxygen binds to purple-red myoglobin (Mb), and red
oxymoglobin (MbO2) forms. In Mb and MbO2) the heme iron is in the
Fe2+ state. Mb and MbO2 can be oxidized, through auto-oxidation,
changing the heme iron from Fe2+ to Fe3+. In the Fe3+ state, it is
called metmyoglobin (MMb) and has an undesirable brown-red colour.
Interconversion between the three forms occurs readily.
(MbO2)
oxymyoglobin
(red, Fe2+)
(Mb)
(MMb)
myoglobin
metmyoglobin
2+
(purple-red, Fe )
(brown, Fe3+)
The stability of colour and the rate of brown MMb formation from
auto-oxidation can be minimized if the meat is stored in conditions
free of oxygen by using packaging films with low gas permeabilities. Air
is removed from the package and a storage gas (100% CO2) is injected.
1) Maillard reaction
Chemical composition of the foods affected condensation reaction
between an amino group on an amino acid or protein and a reducing
sugar (glucose or lactose). The presence of the amino acid lysine
results in the most browning colour and cysteine the least colour.
Foods containing lysine, for example, milk, brown readily.
Example include:
- Heating sugar and cream to make toffees, caramels and fudges
- milk chocolate
Products include:
- desirable and undesirable colours (characteristic golden-brown
colour is desirable)
- change in smell and flavour (caramel aroma)
2) Caramelization
Chemical composition of the food affected foods with a high
carbohydrate content, especially sucrose and reducing sugars,
without nitrogen-containing compounds. Factors that increase the
rate of the reaction are acid- or base- catalysed at pH above 9 or
below 3; a temperature above 120C that occurs during the baking
and roasting of foods with a high sugar content
Examples include the browning on the top of baked egg dishes
Products include:
- volatile caramel aromas
- brown caramel-coloured products
B) F6 Texture
Dispersed System a kinetically stable mixture of 1 phase
in Food
in another largely immiscible phase
Dispersed Systems:
1)
Solid-Liquid Dispersions
Suspensions
solid particles dispersed in a liquid
blood (solid red & white cells remain suspended in plasma), molten
chocolate
Gels
liquid particles dispersed in a solid
fruit jelly where the water is trapped in protein mix
2)
3)
Emulsifiers
substances which aid the dispersion of immiscible droplets and stabilize
them to prevent them from separating or forming large chunks
to make an emulsion, oil, water, an emulsifier and mechanical energy
(beating or mixing) are needed
Two Types of Food Emulsions:
1) Water in Oil Emulsions (butter)
Dispersion of water droplets in an oil phase
2) Oil in Water Emulsions (milk & salad dressing)
Dispersion of oil droplets in a continuous water phase
C) Action/Function of Emulsifiers
1) Help with the formation of emulsions and foams
2) Act as the interface (surface) between the liquid, solid, gas phases in
the disperses system
3) To be soluble in fats (oils) and water
Common Emulsifiers
Lecithin (egg yolk), milk protein, salts of fatty acids
F8 Antioxidants
Antioxidant A substance that delays the onset or slows
the rate of oxidation. Used to extend shelf
life of food
2)
Vitamin E (tocopherols)
Wheat germ, nuts, seeds, whole grains, green leafy vegetables,
vegetable (canola) oil, soya beans
3)
B-carotene
Carrots, squash, broccoli, sweet potatoes, tomatoes, kale,
cantaloupe, melon, peaches, apricots
4)
Selenium
Fish, shellfish, red meat, eggs, grains, chicken, garlic
Synthetic Antioxidants
1)
2)
3)
propyl gallate, PG
4)
trihydroxybutyrophenone, THBP
5)
tert-butylhydroquinone, TBHQ
R + AH R-H + A
RO + AH R-O-H + A
ROO + AH R-O-O-H + A
R + A R-A
RO + A R-O-A
EDTA
3.
Reducing Agents (oxidizes and loses e-s itself but causes others to
reduce and gain e-s)
Electron donors and remove or reduce concentrations of oxygen
Examples include ascorbic acid (vitamin C) and carotenoids
Ex.
Oxidation of vitamin C
F9 Stereochemistry in food
Enantiomers
There are three different conventions used for naming the different
Enantiomeric forms.
1. (+) or d and (-) l notation
+ or d (dextrorotatory)
Rotatates the plane of polarized
light clockwise or to the right
Has a positive rotation value
- or l (laevorotatory)
Rotates the plane of polarized light
counter clockwise or to the left
Has a negative rotation value
C C C H
D-glyceraldehyde
L-glyceraldehyde
D-alanine
L-alanine
3. R,S Notation
used by chemists when dealing w/ stereoisomers other than
carbohydrates or amino acids
substituents are labeled around the chiral carbon atom according to CIP
rules (Cahn-Ingold-Prelog)
CIP priority rules:
1) substituent w/ highest atomic # = 1
lowest atomic # = 4
2) if atoms are same, look at the 2nd, 3rd, etc.
4) view molecule w/ lowest ranking substituent behind or
pointing away from you
5) if substituents clockwise around C
R-enantiomer
counterclockwise
S-enantiomer
Ex.
C C C OH
R-lactic acid
S-lactic acid
Ex.
2-bromobutane
R-2-bromobutane
Note:
S-2-bromobutane
R-(-)-carvone
D-(-)-carvone
S-(+) carvone
L-(+) carvone
Spearmint Taste
Ex.
Anthocyanins
Contain the characteristic C6C3C6 flavonoid skeleton with conjugated double
bonds (pi electrons). The more extensive the conjugation, the lower the
energy (longer the wavelength) of the light absorbed. This can be
exemplified using cyaniding. In acidic solution it forms a positive ion and
there is less conjugation than in alkaline solution where the pi electrons in
the extra double bond between the carbon and oxygen atom are also
delocalized. The difference in colour depending on pH explains why poppies,
which have acidic sap, are red whereas cornflowers, which also contain
cyaniding but have alkaline sap, are blue. They differ in the number of
hydroxyl and/or methoxy groups present; the types, numbers and sites of
attachments of sugars to the molecule; and the types and number of
aliphatic or aromatic acids that are attached to the sugars in the
molecule. Examples include quercetin.The basic flavonoid C6C3C6 backbone is
essentially non-polar. As more polar hydroxyl groups are added the
potential for them to form hydrogen bonds with water molecules increases
and many anthocyanins, such as cyaniding with several OH groups, are
appreciably soluble in water for this reason.
Carotenoids
In carotenoids the conjugation is mainly due to a long hydrocarbon chain
(as opposed to the ring system in anthocyanins) consisting of alternate
single and double carbon to carbon bonds. The majority are derived form a
40-carbon polyene chain, which may be terminated by cyclic end-groups
and may be complemented with oxygen-containing functional groups. The
hydrocarbon carotenoids are known as carotenes, while the oxygenated
derivatives are known xanthophylls. Examples include - and -carotene,
vitamin A. - and -carotene and vitamin A are all fat soluble and not
water soluble. Although vitamin A does contain one polar hydroxyl group
the rest of the molecule is a large non-polar hydrocarbon.
Heme and Chlorophyll
Contain a planar heterocyclic unit called a porphin whose structure contains
a cyclic system of conjugated double bonds. The cyclic systems carbon
atoms are sp2 hybridized. This results in a planar structure with extensive
pi conjugation. Porphins with substituents in positions 1 to 8 are called
porphyrins.Porphins contain four nitrogen atoms. The non-bonding pairs of
electrons on the nitrogen atoms enable the porphin to form coordinate
bonds with metal ions.
Solubility
Anthocyanins have many OH groups attached to their ring structure.
They can therefore form hydrogen bonds w/ water thus tend to be
water soluble
Carotenoids have long hydrophobic hydrocarbon chains that will prove to
be more nonpolar than polar. They will tend to be insoluble in water, but
soluble in oils and fats