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10 Colorants
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range to which the eye is sensitive is referred to as visible light Visible light depending on an individual s sensitivity. encompasses wavelengths of approximately 380 770 nm This range makes up a very small portion of the electromagnetic. spectrum Fig 1 In addition to obvious colors hues black white and intermediate grays are also regarded as colors. Pigments are natural substances in cells and tissues of plants and animals that impart color Dyes are any substances that lend. color to materials The term dye is commonly used in the textile industry In the U S food industry a dye is a food grade water. soluble colorant certified by the U S Food and Drug Administration FDA These specific dyes are referred to as certified. colors and each one is assigned an FD C number The FD C designation means that the dye may be used in foods drugs. and cosmetics Added to the approved list of certified colors are the FD C lakes Lakes are dyes extended on a substratum. and they are oil dispersible The dye substratum combination is achieved by adsorption coprecipitation or chemical reaction. The complex involves a salt of a water soluble primary dye and an approved insoluble base stratum Alumina is the only. approved substratum for preparing FD C lakes In addition there are other dyes or lakes approved for use in other countries. where specifications are established by the European Economic Community EEC or the World Health Organization WHO. Colorants exempt from certification may also be used These are natural pigments or substances synthesized but identical to the. natural pigment A classification of colorants and an example within each class are given in Table 1. Color and appearance are major if not the most important quality attributes of foods It is because of our ability to easily. perceive these factors that they are the first to be evaluated by the consumer when purchasing foods One can provide. consumers the most nutritious safest and most economical foods but if they are not attractive purchase will not occur The. consumer also relates specific colors of foods to quality Specific colors of fruits are often associated with maturity while. redness of raw meat is associated with freshness a green apple may be judged immature although some are green when ripe. and brownish red meat as not fresh, Color also influences flavor perception The consumer expects red drinks to be strawberry raspberry or cherry flavored. yellow to be lemon and green to be lime flavored The impact of color on sweetness perception has also been demonstrated It. should also be noted that some substances such as b carotene or riboflavin are not only colorants but nutrients as well It is clear. Electromag netic spectrum,TABLE 1 Classification of Colorants. Colorant Example,A Certified,1 Dye FD C Red No 40,2 Lake Lake of FD C Red No 40. B Exempt from certification, 1 Natural pig ments Anthocyanin juice concentrate annatto extract. 2 Synthetic nature identical b Carotene, therefore that color of foods has multiple effects on consumers and it is wrong to regard color as being purely cosmetic.
Many food pigments are unfortunately unstable during processing and storage Prevention of undesirable changes is usually. difficult or impossible Depending on the pigment stability is impacted by factors such as the presence or absence of light. oxygen heavy metals and oxidizing or reducing agents temperature and water activity and pH Because of the instability of. pigments colorants are sometimes added to foods, The purpose of this chapter is to provide an understanding of colorant chemistry an essential prerequisite for controlling the. color and color stability of foods,10 2 Pigments in Animal and Plant Tissue. 10 2 1 Heme Compounds, Heme pigments are responsible for the color of meat Myoglobin is the primary pigment and hemoglobin the pigment of blood. is of secondary importance Most of the hemoglobin is removed when animals are slaughtered and bled Thus in properly bled. muscle tissue myoglobin is responsible for 90 or more of the pigmentation The myoglobin quantity varies considerably among. muscle tissues and is influenced by species age sex and physical activity For example pale colored veal has a lower. myoglobin content than red colored beef Muscle to muscle differences within an animal also are apparent and these. differences are caused by varying quantities of myoglobin present within the muscle fibers Such is the case with poultry where. light colored breast muscle is easily distinguished from the dark muscle color of leg and thigh muscles Listed in Table 2 are the. major pigments found in fresh cured and cooked meat Other minor pigments present in muscle tissue include the cytochrome. enzymes flavins and vitamin B12,10 2 1 1 Myoglobin hemoglobin. Structure of Heme Compounds, Myoglobin is a globular protein consisting of a single polypeptide chain Its molecular mass is 16 8 kD and it is comprised of.
153 amino acids This protein portion of the molecule is known as globin The chromophore component responsible for light. absorption and color is a porphyrin known as heme Within the porphyrin ring a centrally located iron atom is complexed with. four tetrapyrrole nitrogen atoms Thus myoglobin is a complex of globin and heme The heme porphyrin is present within a. hydrophobic pocket of the globin protein and bound to a histidine residue Fig 2 The centrally located iron atom shown. possesses six coordination sites four of which are occupied by the nitrogen atoms within the tetrapyrrole ring The fifth. coordination site, TABLE 2 Major Pig ments Found in Fresh Cured and Cooked Meat. Pig ment Mode of formation State of iron State of hematin nucleus State of g lobin Color. 1 Myog lobin Reduction of metmyog lobin Fe 2 Intact Native Purplish red. deoxyg enation of oxymyog lobin, 2 Oxymyog lobin Oxyg enation of myog lobin Fe 2 Intact Native Brig ht red. 3 Metmyog lobin Oxidation of myog lobin Fe 3 Intact Native Brown. oxymyog lobin, 4 Nitric oxide myog lobin Combination of myog lobin with Fe 2 Intact Native Brig ht red pink. nitrosomyog lobin nitric oxide, 5 Nitric oxide metmyog lobin Combination of metmyog lobin with Fe 3 Intact Native Crimson. nitrosometmyog lobin nitric oxide, 6 Metmyog lobin nitrite Combination of metmyog lobin with Fe 3 Intact Native Reddish brown.
excess nitrite, 7 Globin myohemochromog en Effect of heat denaturing ag ents Fe 2 Intact usually bound to Denatured Dull red. on myog lobin oxymog lobin denatured protein other than usually. irradiation of g lobin g lobin detached,hemichromog en. table continued on next page,table continued from previous page. Pig ment Mode of formation State of iron State of hematin nucleus State of g lobin Color. 8 Globin myohemichromog en Effect of heat denaturing ag ents Fe 3 Intact usually bound to Denatured Brown. on myog lobin oxymog lobin denatured protein other than usually sometimes. metmyog lobin hemochromog en g lobin detached g reyish. 9 Nitric oxide myohemochromog en Effect of heat denaturing ag ents Fe 2 Intact Denatured Brig ht red pink. on nitric oxide myog lobin, 10 Sulfmyog lobin Effect of H2S and oxyg en on Fe 3 Intact but one double bond Native Green. myog lobin saturated, 11 Metsulfmyog lobin Oxidation of sulfmyog lobin Fe 3 Intact but one double bond Native Red.
12 Choleg lobin Effect of hydrog en peroxide on Fe 2 or Fe 3 Intact but one double bond Native Green. myog lobin or oxymyog lobin effect saturated,of ascorbine or other reducing. ag ent on oxymyog lobin, 13 Nitrihemin Effect of larg e excess nitrite and Fe 3 Intact but reduced Absent Green. 14 Verdohaem Effect of reag ents as in 7 9 in Fe 3 Porphyrin ring opened Absent Green. 15 Bile pig ments Effect of reag ents as in 7 9 in larg e Fe absent Porphyrin ring destroyed Chain Absent Yellow or. excess of porphyrins colorless, From Lawrie 61 courtesy of Perg ammon Press New York. Tertiary structure of myog lobin Ref, is bound by the histidine residue of globin leaving the sixth site available to complex with electronegative atoms donated by. various ligands, Hemoglobin consists of four myoglobins linked together as a tetramer Hemoglobin a component of red blood cells forms.
reversible complexes with oxygen in the lung This complex is distributed via the blood to various tissues throughout the animal. where oxygen is absorbed It is the heme group that binds molecular oxygen Myoglobin within the cellular tissue acts in a similar. fashion accepting the oxygen carried by hemoglobin Myoglobin thus stores oxygen within the tissues making it available for. metabolism,Chemistry and Color Oxidation, Meat color is determined by the chemistry of myoglobin its state of oxidation type of ligands bounds to heme and state of the. globin protein The heme iron within the porphyrin ring may exist in two forms either reduced ferrous 2 or oxidized ferric. 3 This state of oxidation for the iron atom within heme should be distinguished form oxygenation of myoglobin When. molecular oxygen binds to myoglobin oxymyoglobin MbO2 is formed and this is referred to. as oxygenation When oxidation of myoglobin occurs the iron atom is converted to the ferric 3 state forming metmyoglobin. MMb Heme iron in the 2 ferrous state which lacks a bound ligand in the sixth position is called myoglobin. Meat tissue that contains primarily myoglobin also referred to as deoxymyoglobin is purplish red in color Binding of molecular. oxygen at the sixth ligand yields oxymyoglobin MbO2 and the color of the tissue changes to the customary bright red Both the. purple myoglobin and the red oxymyoglobin can oxidize changing the state of the iron from ferrous to ferric If this change in. state occurs through autooxidation these pigments acquire the undesirable brownish red color of metmyoglobin MMb In this. state metmyoglobin is not capable of binding oxygen and the sixth coordination position is occupied by water 25 Shown in. Fig 3 are the various reactions of the heme pigment Color reactions in fresh meat are dynamic and determined by conditions in. the muscle and the resulting ratios of myoglobin Mb metmyoglobin MMb and oxymyoglobin MbO2 Interconversion. among these forms can occur readily, Shown in Fig 4 is the relationship between oxygen partial pressure and the percentage of each type of heme pigment A high. partial pressure of oxygen favors oxygenation forming bright red oxymyoglobin Conversely at low oxygen partial pressures. myoglobin and metmyoglobin are favored In order to enhance oxymyoglobin formation saturation levels of oxygen in the. environment are useful The rate of metmyoglobin formation caused by heme oxidation Fe2 Fe3 can be minimized if. oxygen is totally excluded Muscles have varying oxygen partial pressures causing the ratios of each of the pigment forms to. Presence of the globin protein is known to decrease the rate of heme oxidation Fe2 Fe3 In addition oxidation occurs. more rapidly at lower pH values Furthermore the rate of autoxidation of oxymyoglobin occurs more slowly than that of. myoglobin The presence of trace metals especially copper ions is known to promote autoxidation. Myog lobin reactions in fresh and cured,meats ChMb cholemyg lobin oxidized. porphyrin ring O 2Mb oxymyog lobin,Fe 2 MMb metmyog lobin Fe 3 Mb. myog lobin Fe 2 MMb NO 2,metmyog lobin nitrite NOMMb.
nitrosylmetmyog lobin NOMb,nitrosylmyog lobin NMMb. nitrometmyog lobin NMb,nitromyog lobin the latter two. being reaction products of nitrous acid and,the heme portion of the molecule R. reductant O strong oxidizing conditions,From Ref 31. Influence of oxyg en partial pressure,three chemical states of myog lobin.
From Ref 29,Chemistry and Color Discoloration, Two different reactions can cause green discoloration of myoglobin 61 Hydrogen peroxide can react with either the ferrous or. ferric site of heme resulting in choleglobin a green colored pigment Also in the presence of hydrogen sulfide and oxygen. green sulfomyoglobin can form It is thought that hydrogen peroxide and or hydrogen sulfide arise from bacterial growth A third. mechanisms for green pigmentation occurs in cured meats and is mentioned later. 10 2 1 2 Cured Meat Pigments, During the curing process specific reactions occur that the responsible for the stable pink color of cured meat products These. reactions are outlined in Fig 3 and the compounds responsible for the reactions are listed in Table 2. The first reaction occurs between nitric oxide NO and myoglobin to produce nitric oxide myoglobin MbNO2 also know as. nitrosylmyoglobin MbNO2 is bright red and unstable Upon heating the more stable nitric oxide myohemochromogen. nitrosylhemochrome forms This product yields the desirable pink color of cured meats Heating of this pigment denatures. globin but the pink color persists If metmyoglobin is present it has been postulated that reducing agents are required to convert. metmyoglobin to myoglobin before the reaction with nitric oxide can take place Alternatively nitrite can interact directly with. metmyoglobin In the presence of excess nitrous acid nitrimyoglobin NMb will form Upon heating in a reducing environment. NMb is converted to nitrihemin a green pigment This series of reactions causes a defect known as nitrite burn. In the absence of oxygen nitric oxide complexes of myoglobin are relatively stable However especially under aerobic. conditions these pigments are sensitive to light If reductants are added such as ascorbate or sulfhydryl compounds the. reductive conversion of nitrite to nitric oxide is favored Thus under these conditions formation of nitric oxide myoglobin occurs. more readily Detailed reviews on the chemistry of cured meat pigments are available 31 32. 10 2 1 3 Stability of Meat Pigments, Many factors operative in a complex food system can influence the stability of meat pigments In addition interactions between. these factors are critical and make it difficult to determine cause. and effect relationships Some environmental conditions that have important effects on meat color and pigment stability include. exposure to light temperature relative humidity pH and the presence of specific bacteria Review papers on this subject are. available 25 57, Specific reactions such as lipid oxidation are known to increase the rate of pigment oxidation 26 Similarly color stability can. be improved by the addition of antioxidants such as ascorbic acid vitamin E butylated hydroxyanisole BHA or propyl gallate. 38 These compounds have been shown to delay lipid oxidation and improve retention of color in tissues Other biochemical. factors such as the rate of oxygen consumption prior to slaughter and activity of metmyoglobin reductase can influence the. color stability of fresh meat 67,10 2 1 4 Packaging Considerations.
An important means of stabilizing meat color is to store it under appropriate atmospheric conditions The problem of. discoloration caused by heme oxidation Fe2 Fe3 can be resolved by using modified atmosphere MA packaging This. technique requires the use of packaging films with low gas permeabilities After packaging air is evacuated from the package. and the storage gas is injected By employing oxygen enriched or devoid atmospheres color stability can be enhanced 75. Muscle tissue stored under conditions devoid of O2 100 CO2 and in the presence of an oxygen scavenger also exhibits good. color stability 86 Use of modified atmosphere packaging techniques may however result in other chemical and biochemical. alterations that can influence the acceptability of meat products Part of the influence of modified atmospheres on pigment. stability no doubt relates to its influence on microbial growth Further information on use of MA for fresh meat storage can be. found in a review article by Seideman and Durland 96. 10 2 2 Chlorophyll, 10 2 2 1 Structure of Chlorophylls and Derivatives. Chlorophylls are the major light harvesting pigments in green plants algae and photosynthetic bacteria They are magnesium. complexes derived from porphin Porphin is a fully unsaturated macrocyclic structure that contains four pyrrole rings linked by. single bridging carbons The rings are numbered I through IV or A through D according to the Fisher numbering system Fig 5. Pyrrole carbon atoms on the periphery of the porphin structure are numbered 1 through 8 Carbon atoms of the bridging. carbons are designated alpha beta gamma and delta The IUPAC numbering system for porphin is shown in Figure 5b The. more common numbering system is the Fisher system, Substituted porphins are name porphyrins Phorbin Fig 5c is considered to be the nucleus of all chlorophylls and is formed by. the addition of a fifth isocyclic ring V to porphin A porphyrin is any macrocyclic tetrapyrrole pigment in which the pyrrole rings. are joined by methyne bridges and the system of double bonds forms a closed conjugated loop Chlorophylls therefore are. classified as porphyrins, Several chlorophylls are found in nature Their structures differ in the substituents around the phorbin nucleus Chlorophyll a and. b are found in green plants in an approximate ratio of 3 1 They differ in the carbon C 3 substituent Chlorophyll a contains a. methyl group while chlorophyll b contains a formyl groups Fig 5d Both chlorophylls have a vinyl and an ethyl group at the C. 2 and C 4 position respectively a carbomethoxy group at the C 10 position of the isocylic rings and a phytol group esterfied. to propionate at the C 7 position Phytol is a 20 carbon monounsaturated isoprenoid alcohol Chlorophyll c is found in. association with chlorophyll a in marine algae dinoflagellates and diatoms Chlorophyll d is a minor constituent accompanying. chlorophyll a in red algae Bacteriochlorophylls and chlorobium chlorophylls are principal chlorophylls found in purple. photosynthetic bacteria and green sulfur bacteria respec. Structure of porphin a b phorbin c and chlorophyll chl d. TABLE 3 Nomenclature of Chlorophyll Derivatives, Phyllins Chlorophyll derivatives containing mag nesium. Pheophytins The mag nesium free derivatives of the chlorophylls. Chlorophyllides The products containing a C 7 propionic acid resulting from enzymic or chemical. hydrolysis of the phytyl ester, Pheophorbides The products containing a C 7 propionic acid resulting from removal of.
mag nesium and hydrolysis of the phytyl ester, Methyl or ethyl The corresponding 7 propionate methyl of ethyl ester. pheophorbides, Pyro compounds Derivatives in which the C 10 carbomethoxy g roup has been replaced by. Meso compounds Derivatives in which the C 2 vinyl g roup has been reduced to ethyl. Chlorins e Derivatives of pheophorbide,a resulting from cleavag e of the isocyclic ring. Rhodins g The corresponding derivatives from pheophorbide. tively Trivial names are widely used for chlorophylls and their derivatives 49 Listed in Table 3 are the names used most often. Figure 6 is a schematic representation of the structural relationships of chlorophyll and some of its derivatives. 10 2 2 2 Physical Characteristics, Chlorophylls are located in the lamellae of intercellular organelles of green plants known as chloroplasts They are associated. with carotenoids lipids and lipoproteins Weak linkages non covalent bonds exist between these molecules The bonds are. easily broken hence chlorophylls can be extracted by macerating plant tissue in organic solvents Various solvents have been. used Polar solvents such as acetone methanol ethanol ethyl acetate pyridine and dimethylformamide are most effective for. complete extraction of chlorophylls Nonpolar solvents such as hexane or petroleum ether are less effective High performance. liquid chromatography HPLC today is the method of choice for separating individual chlorophylls and their derivatives In the. case of chlorophyll a and b for example the increase in polarity contributed by the C 3 formyl substituent of chlorophyll b. causes it to be more strongly adsorbed on a normal phase column and more weakly absorbed on a reverse phase column than. chlorophyll a 14, Identification of chlorophyll and its derivatives is to a large extent based on absorption characteristics of visible light Visible.
spectra of chlorophyll a and b and their derivatives are characterized by sharp light absorption bands between 600 and 700 nm. red regions and between 400 and 500 nm blue regions Table 4 The wavelength of maximum absorption for chlorophylls a. and b dissolved in ethyl ether are respectively 660 5 and 642 nm in the red region and 428 5 and 452 5 nm in the blue region. 10 2 2 3 Alterations of Chlorophyll, Chlorophyllase is the only enzyme known to catalyze the degradation of chlorophyll Chlorophyllase is an esterase and in vitro. it catalyzes cleavage of phytol from chlorophylls and its Mg free derivatives pheophytins forming chlorophyllides and. pheophorbides respectively Fig 6 Its activity is limited to porphyrins with a carbomethoxy groups at C 10 and hydrogens at. positions C 7 and C 8 73 The enzyme is active in solutions containing water alcohols or acetone In the presence of large. amounts of alcohols such as methanol or ethanol the phytol group is removed and the chlorophyllide is esterified to form either. methyl or ethyl chlorophyllide Formation of chlorophyllides in fresh leaves does not occur until the enzyme has been heat. activated postharvest The optimum temperature for chlorophyllase activity in vegetables ranges. Chlorophyll and its derivatives, TABLE 4 Spectral Properties in Ethyl Ether of Chlorophyll. a and b and Their Derivatives,Absorption maxima nm. Ratio of Molar,Red Blue absorption absorptivity,Compound reg ion reg ion blue red red reg ion. Chlorophylla 660 5 428 5 1 30 86 300,Methyl chlorophyllidea 660 5 427 5 1 30 83 000b.
Chlorophyllb 642 0 452 5 2 84 56 100,Methyl chlorophyllideb 641 5 451 0 2 84 b. Pheophytina 667 0 409 0 2 09 61 000b,Methyl pheophorbidea 667 0 408 5 2 07 59 000b. Pheophytinb 655 434 37 000c,Pyropheophytina 667 0 409 0 2 09 49 000b. Zinc pheophytina 653 423 1 38 90 300d,Zinc pheophytinb 634 446 2 94 60 200d. Copper pheophytina 648 421 1 36 67 900d,Copper pheopytinb 627 438 2 53 49 800d.
Strain et al 99,b Penning ton et al 80,cDavidson 20. d Jones et al 55, between 60 and 82 2 C 64 Enzyme activity decreases when plant tissue is heated above 80 C and chlorophyllase loses its. activity if heated to 100 C Chlorophyllase activity in spinach during growth and fresh storage is shown in Figure 7 Maximum. activity is observed at the time the plant begins flowering solid line Postharvest storage of fresh spinach at 5 C decreases. enzyme activity compared to activities measured at the time of harvest broken line 122. Chlorophyllase activity expressed as,percent conversion of chlorophyll to. chloro phyllide in spinach during,g rowth solid line and after storag e. at 5 C broken line From Ref 112,Heat and Acid, Chlorophyll derivatives formed during heating or thermal processing can be classified into two groups based on the presence or.
absence of the magnesium atom in the tetrapyrrole center Mg containing derivatives are green in color while Mg free. derivatives are olive brown in color The latter are chelators and when for example sufficient zinc or copper ions are available. they will form green zinc or copper complexes, The first change observed when the chlorophyll molecule is exposed to heat is isomerization Chlorophyll isomers are formed by. inversion of the C 10 carbomethoxy group The isomers are designated as a and b They are more strongly absorbed on a C. 18 reverse phase HPLC column than are their parent compounds and clear separation can be achieved Isomerization occurs. rapidly in heated plant tissue or in organic solvents Establishment of equilibrium in leaves results in conversion of 5 10 of. chlorophyll a and b to a and b after heating for 10 min at 100 C 3 92 113 Chromatograms of a spinach extract of fresh. versus blanched spinach in Figure 8 show isomer formation during heating. The magnesium atom in chlorophyll is easily displaced by two hydrogen ions resulting in the formation of olive brown. pheophytin Fig 9 The reaction is irreversible in aqueous solution Compared to their parent compounds pheophytin a and b. are less polar and more strongly absorbed on a reverse phase HPLC column Formation of the respective pheophytins occur. more rapidly from chlorophyll a than from chlorophyll b Chlorophyll b is more heat stable. Hig h performance liquid chromatog raphy HPLC, chromatog rams of chlorophylls chl and derivatives in fresh. blanched frozen and canned spinach Phe pheophytin Pyro. pyropheophytin From Ref 92, Formation of pheophytin and pyropheophytin from chlorophyll.

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