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Option F: FOOD CHEMISTRY

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.

Straight Chain Glucose


CHO

Ring Form Glucose

Monosaccharides can undergo condensation rxns to make dissacharides


and polysaccharides
Disaccharide examples include lactose and maltose
Polysaccharide examples include starch and cellulose
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

3. Lipids (Fats & Oils)


Are triesters/triglycerides formed from condensation rxns btw
propane-1,2,3-triol (glycerol) with 3 chains of carboxylic acids (fatty
acids)
General formula of a fat or oil:

H2C-O-C-R1
H2C-O-C-R2

R1, R2, and R3 are long chain


chain hydrocarbons which may be
the same or different

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)

Balanced Diet: 60% carbohydrate


20-30% protein
10-20% lipid
Vitamins & Minerals included in 3 above
2 dm3 water
too much or little results in malnutrition
F2 Fats & Oils
Structures of Saturated & Unsaturated Fatty Acids
Most naturally occurring fats contain a mix of saturated, monounsaturated, & polyunsaturated fatty acids
Common fatty acids (page 146 in SG)

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

Unsaturated fatty acids my be in cis-form or trans-form


cis,cis-linoleic acid

trans,trans-linoleic acid

Physical properties of Fats & Oils


The melting point and the degree of crystallization (solidification) depends
on:
1) The length of the hydrocarbon chains
Mp of fatty acids increases w/ increasing molar mass
Ex. Stearic (saturated) acid w/ 18 C: mp = 69.6C
Lauric (saturated) acid w/ 12 C: mp = 44.2C
2)

The degree of unsaturation


Saturated fatty acids have higher mps than unsaturated fatty
acids
The more unsaturated, the lower the mp and less crystalline it
would be
Ex.

Stearic Acid
18 carbons
no C=C bonds
mp = 69.6C

Linoleic Acid
18 carbons
2 C=C bonds
mp = -5.0C

3) Geometric Isomerism around the double bonds


Saturated fatty acids have tetrahedral sp3 shape that forms a
rigid backbone (109.5 apart)
This leads to a crystalline structure packed closely together by
strong vdWs forces
If C=C double bonds are present, there will now be a 120 bond
angle that interferes w/ the tetrahedral straight rigid chain
producing a kink in the chain
This leads to a less rigid structure and lowering the mp
Trans isomers can pack more closely together resulting in higher mp
than cis isomers

Chemical Properties of Fats & Oils


Unsaturated fats are less stable than saturated fats
C=C double bonds can react w/ water (hydrolysis) in presence of heat or
enzymes. C=C can also react w/ oxygen (auto-oxidation), light (photooxidation), and hydrogen (hydrogenation)

Hydrogenation of Unsaturated Fats

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

Chemical Factors that Affect Shelf Life


1) Water Content

change in water content causes loss of nutrients, browning, and


rancidity
loss of water dries food and changes texture
dry foods become vulnerable to microbes if they absorb water

2) Change in pH

causes changes in flavour (sour w/ low pH), colour, browning, and loss of
nutrients

3) Light Exposure

causes rancidity, vitamin loss, and fading of colour

4) Temperature

higher temperature increases rate of other forms of spoilage

5) Exposure to Air

increases the rate of oxidation

Rancidity is the perception consumers have of lipids, those


that our senses perceives as off because of a
disagreeable smell, taste, texture or appearance
A) Hydrolytic Rancidity

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

propane-1,2,3-triol + fatty acids


(alcohol)
(carbox acids)

Examples of off-flavoured fatty acids:

butanoic, hexanoic, octanoic acid in rancid milk


palmitic, stearic,and oleic acid give chocolate oily flavour
lauric acid gives palm/coconut oil a soapy flavour
butanoic acid (smelly feet) in butter

B) Oxidative Rancidity

due to oxidation of fatty acid chains


addition of O2 across the C=C double bond of unsaturated fatty acids
oily fishes have unsaturation and are prone to oxidation
process catalysed by light and enzymes
process proceeds by free radical mechanism

Free-Radical Chain Mechanism


Initiation unsaturated lipid exposed to light (photo-oxidation)
- initial Ea very high
- hemolytic fission btw C and H bond forming free radicals
R-H R + H
Propagation

(RH = unsaturated fatty acid)

free radicals continue to form chain rxns


- propagate in presence of O2 to form
peroxide radicals (R-O-O)
- ROO may react to form hydroperoxides (R-O-O-H)
R + O2

R-O-O
peroxide radical

R-O-O + H-R

R-O-O-H + R
hydroperoxide

- O2 may initially react w/ alkene in R-H to produce a


hydroperoxide directly
R-H + O2 ROOH
- the weak O-O bond in the hydroperoxide then breaks
either photochemically or by catalysis w/ TM ions to
form/degrade to volatile aldehydes and ketones w/
strong off flavours (spoiling of food)

Termination

- occurs when 2 free radicals combine to form nonradical products


R + R R-R
R + ROO ROOR
ROO + ROO ROOR + O2

Methods to minimize rate of Rancidity and prolong shelf life


A) Packaging

using inert gas to minimize contact w/ O2, covering food


using low gas permeable packaging or hermetic sealing
minimize amount of air in headspace by keeping jars full

B) Processing

limit lipase hydrolysis by storing dairy products at low temperatures


(refrigeration)
reduce light exposure by storing in a dark place
keeping moisture levels low during processing by adding salt, sugar, or
smoking
radiation (gamma or X rays) to destroy microorganisms

C) Additives

sodium sulphite, sodium hydrogensulphite, citric acid to delay the onset


of non-enzymic browning
sodium and potassium nitrite and nitrate for curing meats, fixing
colour, and inhibiting microorganisms

sodium benzoate and benzoic acid as antimicrobial agents in fruit


juices, carbonated beverages, pickles
sorbic acid, propanoic acid, calcium propanoate and sodium propanate
for delaying mould and bacterial growth in breads and cheeses
ethanoic acid and benzoic acid for delaying mould and bacterial growth
in pickled meats and fish products and to add flavour

F4 Colour
The Colour Wheel

An objects colour is seen as it absorbs visible light


You dont see the absorbed portions (wavelengths) of light but will see
the transmitted portions
The observed transmitted light is known as the complimentary colour
Ex. Pumpkins are orange. They absorb blue light.
Dye

- A food-grade synthetic water-soluble colourant.

Pigment

- A naturally occurring colourant found in the cells of plants and


animals.

Synthetic Colourants, Dyes

Many foods contain dyes for colour, and flavour


Identified by numbers
Some have proven to be carcinogenic
Diff countries have diff regulations on acceptable dyes. International
legislation needed for food trade.

Naturally Occurring Pigments


1) Anthocyanins
The most widely occurring pigments in plants
Responsible for the pink, purple and blue colours in fruits and
vegetables, including cranberries, blueberries, strawberries and
raspberries
2)

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.

Factors that Affect The Colour Stability


Factors should include the effects of oxidation, temperature change, pH
change and the presence of metal ions. Students should analyse
absorbance spectra that demonstrate these effects.
1) Anthocyanins
In aqueous solution, equilibrium reaction exists between the four
different structural forms depending on the pH and temperature. They
are most stable and most highly coloured at low pH and temperature.
(A) (AH+)
quinonoid
flavylium
(blue)
(red)

(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.

Non-enzymatic Browning (Maillard Reaction) and


Caramelization That Cause the Browning of Food
Comparisons should include the chemical composition of the foods
affected, factors that increase the rate of the browning, products and
examples.

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

F5 Genetically Modified Foods


Genetically modified (GM) food
derived of produced from a genetically modified organism. The food can
be substantially different from or essentially the same as the
conventional food, in terms of composition, nutrition, taste, smell,
texture and functional characteristics.
Benefits and Concerns of using GM foods
A) Potential Benefits
1) Crops
Enhanced taste and quality, reduced maturation time, increase in
nutrients and yields, improved resistance to disease, pest and
herbicides, enrichments of rice with vitamin A.
2) Animals
Increases resistance, productivity and feed efficiency, better
yields of milk and eggs, improved animal health.
3) Environment
Friendly bio-herbicides and bio-insecticides, conservation of soil,
water and energy, improved natural waste management.
B) Potential Concerns
Links to increased allergies (for people involved in their processing)
The risk of changing the composition of a balances diet by altering the
natural nutritional quality of foods.

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)

Liquids Dispersed in Liquids


Emulsions
stable blend of 2 immiscible liquids
mayonnaise (oil droplets in an aqueous system), cream

3)

Gas Dispersed in Liquids


Foams
gas bubbles trapped in liquid medium
whipped cream or eggs, beer
Aerosols
liquid droplets suspended in a gas (smell in food)

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

Naturally Occurring Antioxidants


1)

Vitamin C (absorbic acid)


Citrus fruits, green peppers, broccoli, green leafy vegetables,
strawberries, red currants, potatoes

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)

butylated hydroxyanisole, BHA

2)

butylated hydroxytoluene, BHT

3)

propyl gallate, PG

4)

trihydroxybutyrophenone, THBP

5)

tert-butylhydroquinone, TBHQ

All examples of synthetic antioxidants given have:


phenolic group (-OH joined directly to a benzene ring)
tertiary butyl group, -C(CH3)3 (a 3 C)
both above are good free radical scavengers (good at stopping radical
propagation)
they react and remove free radicals during oxidation thus prolonging
shelf life

Advantages of Antioxidants in Food


naturally occurring vitamins C, E and carotenoids reduce risk of cancer &
heart disease by inhibiting formation of free radicals
vitamin C is vital for production of hormones & collagen
B-carotene can be added to margarine to provide yellow colour and act
as sign for vitamin A synthesis
Believed to enhance the health effects of other foods and boost overall
health and resilience
Disadvantages of Antioxidants in Food
consumers perceive synthetic antioxidants to be less safe because they
do not occur naturally
natural antioxidants more expensive/less effective than synthetic and
can also add unwanted colour and leave aftertaste to food
synthetic antioxidants classified as food additives and need to be
regulated to ensure their safe use in food, may be difficult to
implement in developing countries

Antioxidants in Traditional Food


many traditional food found in diff cultures contain natural antioxidants
vit C & carotenoids found in many types of fruit & veges
flavonoids (citrus, green tea, red wine, oregano, dark chocolate) linked
to lowering LDL (bad) cholesterol and blood sugar levels which reduce
high blood pressure and prevent the development of cancerous cells
Three Main Types of Antioxidants (HL)
1. Free Radical Inhibitors
Antioxidants (AH) inhibit the formation of free radicals in the initiation
step of auto-oxidation or interrupt the propagation of the free-radical
chain
Free-radical quenchers form stable and less reactive free radicals or
non radical products
AH include BHA, BHT, TBHQ and tocopherols (vit E)
Examples:

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

2. Complexing / Chelating Agents


form irreversible complex w/ metal ions (Fe2+, Al3+) to reduce metal ion
concentrations so that the metal ions in solution are unable to catalyze
the oxidation rxns (catalysts for making hydroperoxides in oxidative
ranc.)
this complexing is called chelating
chelating agents include ethylenediaminetetracetic acid (EDTA), plant
extracts (rosemary, tea, ground mustard) Examples include salts of
EDTA and plants extract (rosemary, tea, ground mustard)
EDTA may inhibit oxidation of Fe2+ Fe3+ in raw beef

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

2 distinct spatial arrangements of a molecule


each containing a chiral carbon
are non-superimposable mirror images
have identical physical & chemical properties
except for rotation of polarized light

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

labels stereoisomers according to the direction they rotate the plane


of polarized light
however, this convention provides no indication of the spatial
arrangement of molecule
2. D,L Notation (unrelated to d and l )
based on the absolute configuration (spatial arrangement) of the 2
enantiomers
D and L system is commonly used for carbohydrates (sugars) and amino
acids
notation referenced to 2,3-dihydroxypropanal (glyceraldehyde)

C C C H

Ex. D,L notation of Glyceraldehyde

D-glyceraldehyde

L-glyceraldehyde

Ex. CORN Rule when naming amino acid stereoisomers


arrange substituents COOH, R, NH2 w/ H in back
if CORN arranged clockwise D-enantiomer
if CORN counterclockwise
L-enantiomer

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.

2-hydroxy propanoic acid

C C C OH

R-lactic acid

S-lactic acid

Ex.

2-bromobutane

R-2-bromobutane

Note:

S-2-bromobutane

Knowing the direction of rotation of plane polarized light alone does


not identify whether a stereoisomer is D,L or R,S. It is also
impossible to predict the direction of rotation for a given absolute
configuration

Properties Enantiomers in Food


the different enantiomeric forms vary in their tastes, odours and toxicity
mst naturally occurring sugars exist in the D form and are sweet
most naturally occurring amino acids are in the L form (D- amino acids
taste sweet, L-amino acids are tasteless)
Ex.

R-(-)-carvone
D-(-)-carvone

S-(+) carvone
L-(+) carvone

Spearmint Taste

Caraway / Dill Taste

Ex.

+(d)-limonene smells like oranges


-(l)-limonene smells like lemons

natural raspberry flavour is due to R-alpha-ionone and synthetic raspberry


flavourings contain both the R and S isomers
other synthetically made foods often contain a racemic mixture of each
enantiomer (50:50)
one tragic example was the drug thalidomide where one enantiomer caused
severe defects in unborn children
F10 Chemical Structure and Colour
Observing Colour in Organic Molecules
When electrons are excited, they must fluoresce back down to a lower
energy level. When they do this, they will emit energy.
The amount of energy involved w/ organics is usually quite high,
therefore would only emit in the UV region, thus being colourless
Some organics, especially ones that have extensive conjugation (many
alternating C=C double bonds in benzene rings that have delocalized pi
electrons) will have their electrons absorb then emit energy in the
visible region
Good examples of natural pigments that have delocalization of electrons
(have benzene rings) include: anthocyanins, carotenoids, chlorophyll, and
heme

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.

Chlorophyll: This is a magnesium porphyrin complex with the original


double bond between positions 7 to 8 now saturated and an R group on
C3. It is found in two forms: chlorophyll a and b, which differ in
substituent R group. In chlorophyll a, R is a CH3 group and in chlorophyll
b, R is a CHO group.
Heme: Hemoglobin is the oxygen carrier found in mammalian blood.
Myoglobin is the primary pigment in the muscle tissue and hemoglobin is
the pigment in blood. Myoglobin is a complex of globin (a protein) and
heme (porphyrin ring containing a central iron atom).
Explain why anthocyanins, carotenoids, chlorophyll and heme form coloured
compounds while many other organic molecules are colourless.
The nature of chromophores, conjugation effects and characteristic
absorptions are required. Students should understand how the
wavelength of energy absorbed relates to the colour the food appears.

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