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OPTION F:FOOD CHEMISTRY
       F4 COLOUR
F.4.1: DISTINGUISH BETWEEN A DYE
            AND A PIGMENT
• Dye: Synthetic compounds which are added to
  food to enhance its appearance.
• Pigment: defined as naturally occurring
  colours found in the cells of animal and plants.
DYE                     PIGMENT


• Dye are soluble in water.   Insoluble in water
• Composed of organic         Composed of inorganic
  substances.                 substances
F4.2 EXPLAIN THE OCCURRENCE OF COLOUR
    IN NATURALLY OCCURRING PIGMENTS
Role of pigments in reflecting colour of foods into our
  eyes.

• A pigment is a naturally occurring colour found in the
  cells of plants and animals
• The pigments have colour because of their ability to
  reflect or emit different quantities of energy at
  wavelengths able to stimulate the retina in the eye.
• They absorb light in the visible region of the
  electromagnetic spectrum and transmit the remaining
  light in the visible spectrum which has not been
  absorbed
Examples of the common naturally occurring
pigments

• Poriphyrins (Chlorophyll and Haem)
• Carotenoids
• Anthocyanins
F4.3 DESCRIBES THE RANGE OF COLOURS AND SOURCES OF
  THE NATURALLY OCCURRING PIGMENTS ANTHOCYANINS,
        CAROTENOIDS, CHLOROPHYLL AND HEME.
Anthocyanins            Carotenoids                      Chlorophyll          Haem


                 Most widely             Most widespread pigments in      Plants, algae, and   Fresh meat
                 occurring pigments in   nature (the large majority are   cyanobacteria
 1)    Source    plants                  produced by algae)




                                              Yellow to red orange        Green                Red (myoglobin
                                              Red astaxanthin                                  responsible for the
                                              (complexed to a protein)                         colour of fresh meat)
                                              is responsible for the
 1)    Colour                                 blue or green colour of
       range                                  live lobster and crabs,
                                              and pink colour of
                                              salmon and flamingo




                 Fruits and vegetables   Banana, carrots, tomatoes,       Green plants         Meat of adult
                  (cranberries,          watermelon, peppers, and                              mammals
                 blueberries,            saffron.                                              (cows, sheeps,
1)    Examples   strawberries, and                                                             horses)
                 raspberries
F4.4
                  DESCRIBE
   THE FACTORS THAT AFFECT
    THE COLOUR STABILITY OF
ANTHOCYANINS,CAROTENOIDS,
    CHLOROPHYLL AND HEME
THE FACTORS THAT AFFECT THE
COLOUR STABILITY OF ANTHOCYANINS
• The structure and colour of anthocyanins
  changes with pH.
• The flavylium cation is bright red in acidic. In
  basic solution, H+ removed from the OH group
  on the left ring to form a quinoidal base which
  is blue. As the colour of anthocyanins is pH
  dependent, they can be used as acid-base
  indicator.
• In aqueous solution, anthocyanins can exist in four
  possible structural forms depending on the pH and
  temperature.
(A)           (AH⁺)         (B)             (C)
 quinonoid flavyium carbinol base chalcone
 (blue)         (red)      (colourless ) (colourless)
Very high pH Low pH               Neutral pH
• At low pH, the AH⁺ predominates and the
   mixture is red, at neutral pH values there is
   sufficient concentration of OH ions for this to
   hydrolyse and the solution becomes
   colourless as it is converted to B and C. At
   greater pHs the AH⁺ in eqm with this is
   converted to A and the solution turns to blue
   and form this product
• As the stability of anthocyanins is also affected by
  the temperature, the colour of anthocyanins can vary
  significantly during the cooking process.
• The anthocyanins is most stable and most highly
  coloured at low pH and low temperature.
• When exposed to heat the eqm moves to the right
  and the compounds are less thermodynamically
  stable. This causes a loss of colour and browning.
• The anthocyanins also form deeply coloured
  coordination complexes with Fe3+ and Al3+ ions
  that are present in metal cans and this lead to
  discolouration in canned fruit.
THE FACTORS THAT AFFECT THE
 COLOUR STABILITY OF CAROTENOIDS
• Carotenoids are highly unsaturated molecule and
  the presence of carbon-carbon double bonds
  makes them susceptible to chemical attack.
• Degradation pathways include
  isomerization, oxidation and decomposition of
  the carotenoids molecule.
• Light, enzymes and reaction with hydroperoxides
  (from the oxidation of lipids) causes oxidation
  that will results in the bleaching of
  colour, unpleasant off odours and loss of vitamin
  A activity
• Carotenoids are stable up to 50°C and in the
  pH range 2 – 7 and therefore not degraded by
  most forms of food processing. When heated
  the naturally occurring trans- isomer
  rearranges to the cis- isomer.
THE FACTORS THAT AFFECT THE
COLOUR STABILITY OF CHLOROPHYLL
 Chlorophyll contains a group with 4
 nitrogen atoms which is called a
 porphin.
  The porphin ring forms a very stable
 complex with Mg ion.
 The stability of chlorophyll towards
 heat depends on the pH.
 In a basic solution with a pH of 9 it is
 thermodynamically stable but in acidic
 solution with a pH of 3 is unstable.
• When heated, the cell membrane of the plant
  deteriorates releasing acids which decrease
  the pH.
• At this lower pH, the 2 H ions will displaces Mg
  ion resulting in formation of an olive-brown
  pheophytin complex.
• The breakdown of the cell during heating also
  increases the susceptibility of chlorophyll to
  decomposition by light (photo-degradation).
THE FACTORS THAT AFFECT THE
      COLOUR STABILITY OF HEME
• In muscles, heme is associated with the purple –
  red protein myoglobin molecule, which binds to
  oxygen molecules to form the red oxymyoglobin
  molecule.
• The Fe2+ is more stable than Fe3+ in the non-polar
  environment provided by the side chain in the
  complex.
• The red oxymyoglobin undergo a slow auto-
  oxidation reaction to form the complex of the
  Fe3+ known as metmyoglobin (brown red).
• To reduce this happen, meat are packed in
  plastic films with low gas permeability and
  stored in an atmosphere of carbon dioxide.
MbO2(red,Fe2+)   Mb(purple-red,Fe2+)   MMb(brown,Fe3+)
Oxymyoglobin      myoglobin            metmyoglobin
ANTHCYANINS CAROTENOIDS                                     CHLOROPHYLL                             HEME
Oxidation     Affects position of         Unsaturated carbon bonds                                                Oxygen binds to purple-red
              equilibrium                 allow for oxidation catalyzed                                           myglobin (Mb), forming red
                                          by light, metals and                                                    oxymyoglobin (MbO2)
                                          hydroperoxides =LOSS of                                                 *Fe2+ in MbO2 and Mb
                                          color (bleached)                                                        Auto-oxidation of MbO2 and
                                                                                                                  Mb = Fe2+ → Fe3+
                                                                                                                  (metmyoglobin, MMb)
                                          *Loss of Vit. A activity =                                              = brown-red color
                                          stinky


Temperature   Higher temperatures =       Stable up to 50°C               Stability depends on pH
              equilibrium shifts to the   Therefore, 50°C+ = LOSS of      High pH (basic) – about pH 9 =
              right =LOSS of color        color                           thermodynamically stable


                                          Increase heat = trans- isomer   Low pH (acidic) – about pH 3 =
                                          rearranges tocis-isomer         thermodynamically unstable (LOSS)


                                                                          Increase heat = deterioration of cell
                                                                          membrane = decreases pH =
                                                                          chlorophyll decomposition by light

pH levels     Low pH levels = greater     Stable in range of pH 2 – pH7
              color                       Therefore, pH < 2 and pH > 7    Refer to temperature
                                          = LOSS of color

Presence of   Can form complexes                                          Structure of chlorophyll contains       Porphin ring forms complex
metal ions    with Al3+ and Fe3+ (in                                      porphin ring (group with 4 nitrogen     with Fe ion.
              tin cans) = LOSS of color                                   atoms) which forms complex with a Mg    Fe2+ in MbO2 and Mb
              of canned foods                                             ion
                                                                          Low pH = Mg ion displaced by 2 H ions
                                                                          =olive-brown pheophytin color
F.4.5: Discuss the safety issues
associated with the use of synthetic
         colorants in food.
Concerns:
• Synthetic dyes are biochemically active
  – Can negatively impact health
     • toxicity is easy to prove
     • chronic health effects are difficult to determine
     • Special concern about carcinogenic effects
  – Standards vary from country to country
     • Malachite green and sudan red are generally banned
•   Synthetic colorants = dyes
    International Numbering System (INS) or E numbers = food additive identifiers
    Artificial dyes are potentially carcinogenic (any substance, radionuclide, or
    radiation that is an agent directly involved in causing cancer) so these particular
    carcinogens are banned in certain countries.
    Therefore in most countries, all ingredients are required to be on packaging labels.
    International Food Concerns:
    Some dyes banned in certain countries but not others. Now with lots of
    international trade, it has become a concern with the use of these particular dyes.
    Possible solution: international legislation on colorant legislation
    Example of International Food/Colorant Concern: Sunset Yellow in M&M's
    Banned in Finland and Norway
•   Potential carcinogen
•   Allergic reaction in people with aspirin intolerance
F.4.6: COMPARE THE PROCESSES OF NON-
ENZYMATIC BROWNING AND CARAMELIZATION
What is enzymatic browning process?
A chemical process which occurs in fruits and
vegetables containing the enzyme
polyphenoloxidase and produce brown
pigments.
MAILLARD REACTION
•    Is a type of non-enzymatic browning which consist of a complex
    series of reactions between amino acids and carbohydrate.
•   Responsible for the smell and colour change of common cooking
    processes.
•   the first step in Maillard browning is condensation reaction of the
    aldehyde group in the reducing sugars with the free amino group of
    an amino acid.
•   leads to the replacement of a C=O bond in the aldehyde group by
    C=N-R bond and the formation of water.
•   Reducing sugar + amino acid → initial condensation product + water
•   Condition: Occur at a faster rate when the temperature is high, siza
    of sugar.
CARAMELIZATION
• process which involve the oxidation of with high
  carbohydrate concentration, (sugar) and it is used
  extensively in cooking which result for the product to be
  brown in colour and have nutty flavour.
• This process occurs when sugar are heated at high
  temperature.
• The compound are dehydrated and double bonds are
  introduced into the structure.
• The small sugar molecules react together to form polymers
  with conjugate bonds which absorb light and thus
  producing the brown colour.
• Equation: Cn (H2O)n → n C + n H2O
• Conditions: extreme pH value, type of sugar used.
• Genetic engineering is important especially to food
  scientists to alter the properties and processing conditions
  of foods.
• Genetic engineering involves the alteration of the DNA.
• In the past, to improve the quality of genes, cross breeding
  was done. But this method is inaccurate and time
  consuming.
• GM corn produce a poisonous compound
to reduce the dependency on pesticides
and herbicides.

• GM hens produce eggs containing human
interferone

• GM cow produce milk rich in nutrients.
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Option f4 f5

  • 2. F.4.1: DISTINGUISH BETWEEN A DYE AND A PIGMENT • Dye: Synthetic compounds which are added to food to enhance its appearance. • Pigment: defined as naturally occurring colours found in the cells of animal and plants.
  • 3. DYE PIGMENT • Dye are soluble in water. Insoluble in water • Composed of organic Composed of inorganic substances. substances
  • 4. F4.2 EXPLAIN THE OCCURRENCE OF COLOUR IN NATURALLY OCCURRING PIGMENTS Role of pigments in reflecting colour of foods into our eyes. • A pigment is a naturally occurring colour found in the cells of plants and animals • The pigments have colour because of their ability to reflect or emit different quantities of energy at wavelengths able to stimulate the retina in the eye. • They absorb light in the visible region of the electromagnetic spectrum and transmit the remaining light in the visible spectrum which has not been absorbed
  • 5. Examples of the common naturally occurring pigments • Poriphyrins (Chlorophyll and Haem) • Carotenoids • Anthocyanins
  • 6. F4.3 DESCRIBES THE RANGE OF COLOURS AND SOURCES OF THE NATURALLY OCCURRING PIGMENTS ANTHOCYANINS, CAROTENOIDS, CHLOROPHYLL AND HEME.
  • 7. Anthocyanins Carotenoids Chlorophyll Haem Most widely Most widespread pigments in Plants, algae, and Fresh meat occurring pigments in nature (the large majority are cyanobacteria 1) Source plants produced by algae) Yellow to red orange Green Red (myoglobin Red astaxanthin responsible for the (complexed to a protein) colour of fresh meat) is responsible for the 1) Colour blue or green colour of range live lobster and crabs, and pink colour of salmon and flamingo Fruits and vegetables Banana, carrots, tomatoes, Green plants Meat of adult (cranberries, watermelon, peppers, and mammals blueberries, saffron. (cows, sheeps, 1) Examples strawberries, and horses) raspberries
  • 8. F4.4 DESCRIBE THE FACTORS THAT AFFECT THE COLOUR STABILITY OF ANTHOCYANINS,CAROTENOIDS, CHLOROPHYLL AND HEME
  • 9. THE FACTORS THAT AFFECT THE COLOUR STABILITY OF ANTHOCYANINS • The structure and colour of anthocyanins changes with pH. • The flavylium cation is bright red in acidic. In basic solution, H+ removed from the OH group on the left ring to form a quinoidal base which is blue. As the colour of anthocyanins is pH dependent, they can be used as acid-base indicator.
  • 10. • In aqueous solution, anthocyanins can exist in four possible structural forms depending on the pH and temperature.
  • 11. (A) (AH⁺) (B) (C) quinonoid flavyium carbinol base chalcone (blue) (red) (colourless ) (colourless) Very high pH Low pH Neutral pH • At low pH, the AH⁺ predominates and the mixture is red, at neutral pH values there is sufficient concentration of OH ions for this to hydrolyse and the solution becomes colourless as it is converted to B and C. At greater pHs the AH⁺ in eqm with this is converted to A and the solution turns to blue and form this product
  • 12. • As the stability of anthocyanins is also affected by the temperature, the colour of anthocyanins can vary significantly during the cooking process. • The anthocyanins is most stable and most highly coloured at low pH and low temperature. • When exposed to heat the eqm moves to the right and the compounds are less thermodynamically stable. This causes a loss of colour and browning. • The anthocyanins also form deeply coloured coordination complexes with Fe3+ and Al3+ ions that are present in metal cans and this lead to discolouration in canned fruit.
  • 13. THE FACTORS THAT AFFECT THE COLOUR STABILITY OF CAROTENOIDS • Carotenoids are highly unsaturated molecule and the presence of carbon-carbon double bonds makes them susceptible to chemical attack. • Degradation pathways include isomerization, oxidation and decomposition of the carotenoids molecule. • Light, enzymes and reaction with hydroperoxides (from the oxidation of lipids) causes oxidation that will results in the bleaching of colour, unpleasant off odours and loss of vitamin A activity
  • 14. • Carotenoids are stable up to 50°C and in the pH range 2 – 7 and therefore not degraded by most forms of food processing. When heated the naturally occurring trans- isomer rearranges to the cis- isomer.
  • 15. THE FACTORS THAT AFFECT THE COLOUR STABILITY OF CHLOROPHYLL Chlorophyll contains a group with 4 nitrogen atoms which is called a porphin. The porphin ring forms a very stable complex with Mg ion. The stability of chlorophyll towards heat depends on the pH. In a basic solution with a pH of 9 it is thermodynamically stable but in acidic solution with a pH of 3 is unstable.
  • 16. • When heated, the cell membrane of the plant deteriorates releasing acids which decrease the pH. • At this lower pH, the 2 H ions will displaces Mg ion resulting in formation of an olive-brown pheophytin complex. • The breakdown of the cell during heating also increases the susceptibility of chlorophyll to decomposition by light (photo-degradation).
  • 17. THE FACTORS THAT AFFECT THE COLOUR STABILITY OF HEME • In muscles, heme is associated with the purple – red protein myoglobin molecule, which binds to oxygen molecules to form the red oxymyoglobin molecule. • The Fe2+ is more stable than Fe3+ in the non-polar environment provided by the side chain in the complex. • The red oxymyoglobin undergo a slow auto- oxidation reaction to form the complex of the Fe3+ known as metmyoglobin (brown red).
  • 18. • To reduce this happen, meat are packed in plastic films with low gas permeability and stored in an atmosphere of carbon dioxide. MbO2(red,Fe2+) Mb(purple-red,Fe2+) MMb(brown,Fe3+) Oxymyoglobin myoglobin metmyoglobin
  • 19. ANTHCYANINS CAROTENOIDS CHLOROPHYLL HEME Oxidation Affects position of Unsaturated carbon bonds Oxygen binds to purple-red equilibrium allow for oxidation catalyzed myglobin (Mb), forming red by light, metals and oxymyoglobin (MbO2) hydroperoxides =LOSS of *Fe2+ in MbO2 and Mb color (bleached) Auto-oxidation of MbO2 and Mb = Fe2+ → Fe3+ (metmyoglobin, MMb) *Loss of Vit. A activity = = brown-red color stinky Temperature Higher temperatures = Stable up to 50°C Stability depends on pH equilibrium shifts to the Therefore, 50°C+ = LOSS of High pH (basic) – about pH 9 = right =LOSS of color color thermodynamically stable Increase heat = trans- isomer Low pH (acidic) – about pH 3 = rearranges tocis-isomer thermodynamically unstable (LOSS) Increase heat = deterioration of cell membrane = decreases pH = chlorophyll decomposition by light pH levels Low pH levels = greater Stable in range of pH 2 – pH7 color Therefore, pH < 2 and pH > 7 Refer to temperature = LOSS of color Presence of Can form complexes Structure of chlorophyll contains Porphin ring forms complex metal ions with Al3+ and Fe3+ (in porphin ring (group with 4 nitrogen with Fe ion. tin cans) = LOSS of color atoms) which forms complex with a Mg Fe2+ in MbO2 and Mb of canned foods ion Low pH = Mg ion displaced by 2 H ions =olive-brown pheophytin color
  • 20. F.4.5: Discuss the safety issues associated with the use of synthetic colorants in food.
  • 21. Concerns: • Synthetic dyes are biochemically active – Can negatively impact health • toxicity is easy to prove • chronic health effects are difficult to determine • Special concern about carcinogenic effects – Standards vary from country to country • Malachite green and sudan red are generally banned
  • 22. Synthetic colorants = dyes International Numbering System (INS) or E numbers = food additive identifiers Artificial dyes are potentially carcinogenic (any substance, radionuclide, or radiation that is an agent directly involved in causing cancer) so these particular carcinogens are banned in certain countries. Therefore in most countries, all ingredients are required to be on packaging labels. International Food Concerns: Some dyes banned in certain countries but not others. Now with lots of international trade, it has become a concern with the use of these particular dyes. Possible solution: international legislation on colorant legislation Example of International Food/Colorant Concern: Sunset Yellow in M&M's Banned in Finland and Norway • Potential carcinogen • Allergic reaction in people with aspirin intolerance
  • 23. F.4.6: COMPARE THE PROCESSES OF NON- ENZYMATIC BROWNING AND CARAMELIZATION What is enzymatic browning process? A chemical process which occurs in fruits and vegetables containing the enzyme polyphenoloxidase and produce brown pigments.
  • 24. MAILLARD REACTION • Is a type of non-enzymatic browning which consist of a complex series of reactions between amino acids and carbohydrate. • Responsible for the smell and colour change of common cooking processes. • the first step in Maillard browning is condensation reaction of the aldehyde group in the reducing sugars with the free amino group of an amino acid. • leads to the replacement of a C=O bond in the aldehyde group by C=N-R bond and the formation of water. • Reducing sugar + amino acid → initial condensation product + water • Condition: Occur at a faster rate when the temperature is high, siza of sugar.
  • 25. CARAMELIZATION • process which involve the oxidation of with high carbohydrate concentration, (sugar) and it is used extensively in cooking which result for the product to be brown in colour and have nutty flavour. • This process occurs when sugar are heated at high temperature. • The compound are dehydrated and double bonds are introduced into the structure. • The small sugar molecules react together to form polymers with conjugate bonds which absorb light and thus producing the brown colour. • Equation: Cn (H2O)n → n C + n H2O • Conditions: extreme pH value, type of sugar used.
  • 26.
  • 27. • Genetic engineering is important especially to food scientists to alter the properties and processing conditions of foods. • Genetic engineering involves the alteration of the DNA. • In the past, to improve the quality of genes, cross breeding was done. But this method is inaccurate and time consuming.
  • 28. • GM corn produce a poisonous compound to reduce the dependency on pesticides and herbicides. • GM hens produce eggs containing human interferone • GM cow produce milk rich in nutrients.