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Flavor Formation
Barbara dAcampora Zellner, Paola Dugo,
Giovanni Dugo, and Luigi Mondello
CONTENTS
12.1 Brief Introduction to Dairy Flavor Formation..................................................... 277
12.2 Flavor Formation in Milk ................................................................................... 279
12.2.1 Milk Flavors Developed During Heat Treatment and Storage............... 279
12.2.2 Flavors Developed from the Autoxidation of Milk Lipids ..................... 280
12.2.3 Light-Induced Flavor Formation ............................................................281
12.2.4 Flavor Compounds Derived from Package Component Migration ........281
12.3 Flavor Formation in Fermented Dairy Products: Cheese..................................... 282
12.3.1 Fermentation of Lactose and Conversion of Citrate ............................... 282
12.3.2 Proteolysis and Catabolism of Amino Acids .......................................... 284
12.3.2.1 Metabolism of Branched-Chain Amino Acids ...................... 285
12.3.2.2 The Catabolism of Aromatic Amino Acids ........................... 285
12.3.2.3 Methionine and Its Catabolic Pathways ............................... 286
12.3.3 Lipolysis and Catabolism of Fatty Acids ................................................ 286
12.4 Concluding Remarks .......................................................................................... 288
References ...................................................................................................................... 288
278
sample, so that raw milk presents a distinct flavor when compared to that of heated or processed
milk, with different classes of compounds responsible for the characteristic flavor of distinct samples. Generally esters are responsible for the flavor of raw milk samples, while lactones and heterocyclic compounds for that of heat-treated and pasteurized milk. On the other hand, fermented
dairy products, such as cheese and yogurt, are characterized by the presence of fatty acids [1].
It is mandatory to highlight that fermentation has a major impact on the organoleptic quality
of milk-derived products. Traditionally, fermentation was primarily applied to improve and prolong shelf-life, since the growth of fermentative microorganisms typically results in the production
of acids or alcohols that inhibits the growth of food pathogens or spoilage organisms preserving
the food. Though the chemical transformation of components in dairy food raw materials, and
the release of microbial metabolites contribute to the flavor, appearance, and texture. In dairy
products, lactose, citrate, milk fat (lipids), and proteins are converted into a broad range of volatile
and nonvolatile flavor compounds.
Three main pathways for the flavor formation of dairy products can be distinguished, i.e.,
glycolysis, proteolysis, and lipolysis [2,3] (see Figure 12.1). These processes may already generate
final flavor compounds, though further reactions can occur yielding an even greater number of
low-molecular weight components that essential to the overall odor of the product.
In general, flavors derived from lactose or citrate (glycolysis), such as lactic acid, acetaldehyde,
and diacethyl (2,3-butanedione), are produced by the lactic flora. Lipids are also another source
of a wide range of dairy flavors, and by means of lipolysis and oxidation are prone to cause hydrolytic and oxidative rancidity, respectively. In this manner, small amounts of - and -hydroxy
acids present in milk lipids can be readily converted to - and -lactones; unsaturated fatty acids
may hydrate to hydroxy acids, and then via oxidation produce - and -lactones; -oxidation,
followed by decarboxylation, produces methyl ketones; and oxidation at double bonds can generate straight-chain aldehydes and ketones, which under reducing conditions may be converted to
the corresponding alcohols. Moreover, protein-derived flavors also comprise a large amount of
pathways; Strecker aldehydes, such as 2-methylpropanal, 2-methylbutanal, and 3-methylbutanal,
can be synthesized via amino acids and, in turn, may produce their corresponding alcohols; and
sulfur-containing compounds, such as hydrogen sulfide, methanethiol, and dimethyl disulfide
(DMDS), can be derived from cysteine and methionine. In addition, other flavor origins have
Milk
Lactose/citrate
Casein
Triglycerides
Pyruvate/-acetolactate
Peptides
Amino acids
Figure 12.1
Flavor Formation
279
been reported, such as compounds derived from lactose, without any interaction of the lactic flora,
that are developed during heat treatment or that result from alkaline degradation of lactose or its
components glucose and galactose, e.g., maltol [4] and 2-acetylfuran [5].
The flavor of cheeses is composed of a blend of compounds generated by all three pathways;
the same is true for key-odor compounds. Cheddar [6] and Camembert [7] cheeses, for instance,
have half of their potent odorants derived from lactose fermentation or citrate degradation, a very
small amount produced by lipolysis, and the other half resulting from amino acid degradation
(leucine and methionine).
Taking into consideration that flavor is the primary index of dairy food acceptance and is strictly
related to product development and improvement, this chapter provides an overview of the dairy flavor formation pathways. Numerous dairy food flavors have been thoroughly studied, though demonstrating that even widely investigated metabolic pathways may continuously reveal new facets. In
this chapter, flavor formation processes in milk and cheese will be dealt with more extensively.
12.2
Fresh, good quality milk is characterized by three features: a characteristic, subtle, and delicate
flavor; a pleasant mouth-feel since it is an emulsion of fat globules dispersed in a colloidal aqueous
solution; and a slightly sweet and salty taste due to the presence of lactose and salts. When compared to other dairy products, such as butter or cheese, the concentration of flavor compounds in
fresh milk is very low.
It is widely accepted that the flavoring compounds in milk are products of the animals metabolism, which is also influenced by the feed. As previously cited, another aspect to be considered
is the samples state, so that the flavor of raw milk is not identical to that of heated or processed
milk. Esters are considered as responsible for the flavor of raw milk samples, while lactones and
heterocyclic compounds for that of heat-treated and pasteurized milk [1].
Furthermore, almost all milk types and milk-derived products are submitted to heat treatments
and storage over a period of time inducing flavor development. In addition, autoxidation of lipids,
light exposure, and also packaging effects, may yield milk flavors. Moreover, considering that milk
is composed of a multitude of compounds belonging to distinct chemical classes, several of these
compounds can be precursors of flavor and off-flavor chemicals. The latter may be defined as an
unpleasant odor or taste imparted to a food sample though internal deteriorative change [8].
12.2.1
Flavor, most frequently off-flavor, development, during heat processes has been already thoroughly
researched, and the formation of ketones, lactones, aldehydes, furans, alcohols, acids, and sulfurcontaining compounds is widely accepted.
Ketones, such as diketones, cyclic ketones, and methyl ketones, formed in heat-processed milks,
are considered as the major contributors to that of matrices cooked and stale flavors [9], while
diketone compounds, diacethyl and 2,3-pentanedione, were described as significant contributors
to the heated, burnt, and fermented notes elicited by heated milk [10]. With regards to diacethyl,
its production is considered to be started by methyl glyoxal, generated by heating lactose, which
then reacts with glycin or its derivatives forming diacethyl. Cyclic ketones, e.g., cyclopentanone
and 2-methyl-tetrahydrofuran-3-one, are also considered as contributors to the heated, burnt, and
fermented notes in heated milk [10].
280
Milk has been studied in depth by Moio et al. [1113], who analyzed the matrix under distinct
conditions. Analyses of raw bovine, ovine, caprine, and water buffalo milk samples demonstrated
that dimethylsulfone, ethyl butanoate, ethyl hexanoate, heptanal, indole, nonanal, and 1-octen-3-ol
are odor-active compounds common to all samples. Even though similarities between the distinct
samples were found, the overall odor of each milk variety presented a different flavor profile, with
ethyl butanoate and ethyl hexanoate as the most potent flavorants in cow, sheep, and goat milk,
while water buffalo milk flavor was better characterized by nonanal and 1-octen-3-ol [11]. On the
other hand, while investigating high-temperature/short-time (HTST) and ultrahigh temperature
(UHT) pasteurized cow milk, dimethylsulfone and 2-heptanone were found to be the most potent
odor-active compounds, instead of ethyl butanoate and ethyl hexanoate observed in raw cow milk.
Both odorant couples, ethyl butanoate and ethyl hexanoate, and dimethylsulfone and 2-heptanone
can be used as aroma quality indicators, for raw and heated milk, respectively [12].
Further compounds that are not detected in raw milk are furans, particularly furfural and
hydroxymethylfurfural (HMF), the former eliciting an almond-like, sweet note, while the latter a
fatty, musty, and waxy odor. Both are formed when milk is heated above 80C by the browning of
a lactosecasein mixture [14], i.e., the casein catalyzed degradation of lactose induced by heat.
The formation of aldehydes is also noteworthy during prolonged storage of casein, these compounds, particularly alkanal compounds and benzaldehyde, are responsible for an unpleasant stale
off-flavor [15]. The production of alkanal compounds can be attributed to the oxidation of lipids
bound by casein, while benzaldehyde can be formed by reactions occurring between phenylalanine and lactose [16,17]. Another class of compounds where formation of milk is induced by heat
treatments is alcohol, most commonly represented by acetol and acetoin (3-hydroxy-2-butanone).
The former is the product of carbohydrate degradation during nonenzymatic browning reactions
[10], while the latter may be formed by the reduction of diacetyl [9]. Both the compounds are also
detected in raw milk, and in increasing concentrations when heated above 90C [10]. Heat treatments can also influence the profile of acids in milk; at temperatures superior to 100C an increment may be observed in the concentrations of acetic, butyric, hexanoic, octanoic, and decanoic
acids [10], contributing to the chemical and rancid flavor of heated milk.
Freshly secreted milk fat does not contain free lactones, but their precursors are present in
bound form [18]. Indeed, small amounts of -hydroxy alkanoic acids esterified to glycerol can be
detected, which, upon hydrolysis during heating or storage, form a homologous series of saturated
aliphatic -lactones. The latter contribute positively to milk flavor eliciting a milky, fatty, and
coconut-like note. Moreover, the cooked flavor, commonly observed in milk and derivative products is caused by hydrogen sulfide. This compound is a product of the oxidation of free sulfhydryl
groups formed in the denaturation of -lactoglobulin, the major whey protein of cows milk [19].
Urbach investigated the effects of cold-storage on raw cow milk samples [20], reporting that
carbonyls are reduced to the corresponding alcohols; among the most abundant ones were ethanol,
2-propanol, and 3-methylbutan-1-ol. After prolonged storage, these alcohols were partially esterified with volatile acids.
Flavor Formation
281
Aliphatic aldehydes are considered as the most important breakdown products of hydroperoxides,
due to their major contribution to unpleasant flavors in food products. Moreover, aldehydes resulting from autoxidation may undergo other reactions, contributing further to the flavor of dairy
products.
12.2.3
Light is known to induce metabolic reactions in dairy products, triggering the degradation of proteins or the oxidation of lipids, resulting in the formation of off-flavors. Furthermore, it is generally
accepted that riboflavin plays a major role as photosensitizer in milk and milk-derived products
[21]. Photosensitized oxidations produce hydroperoxides, which are prone to decompose forming
free radicals, and these are responsible for autoxidation reactions and off-flavor developments.
Riboflavin acts by means of two reaction modes. Type I occurs when a triplet riboflavin (electronic
excited state with two unpaired electrons) is directly deactivated by the abstraction of an electron
from a substrate, which is then oxidized. Subsequently, riboflavin can abstract a further electron,
forming a reduced riboflavin or react with ground-state oxygen to generate a superoxide radical.
Type I reaction may be exemplified by the photoxidation of lipids yielding alkanals and 2-enals,
which are not present in autoxidized milk samples; while 2,4-dienals are only detected in autoxidized samples. According to Wishner [22], the oxidizing substrates in light-exposed milk are the
monoene fatty acids of the triglycerides, while in spontaneously oxidized milk polyene fatty acids
of the phospholipids are involved.
On the other hand, in type II reactions a triplet riboflavin is deactivated physically by oxygen, and a singlet-oxygen is formed. The latter reacts with the amino acid methionine, which
then undergoes Strecker degradation forming aldehydes (e.g., methional) and sulfur-containing
compounds (e.g., dimethyl sulfide). It is noteworthy that the broth and potato-like flavors produced when milk is exposed to light are mainly related to the presence of methional; though the
understanding of the role of this compound in light-induced flavor is made difficult by its easy
conversion to other sulfur compounds [23]. Samuelsson [24] reported that methionine in milk is
converted to mercaptan, sulfides, and disulfides at pH 6.8 in the presence of light and oxygen.
282
nonfat, low-fat, and whole milks, respectively, while chocolate-flavored milk showed a threshold
of 10048 ppb [27]. This information assisted in the prediction of the influence of acetaldehyde
migration on the flavor of milk products.
12.3.1
Flavor formation during the manufacture of cheeses is initiated immediately after the addition of
starter cultures to milk, also known as starter organisms. The widely utilized LAB are able to ferment lactose to lactic acid that on its own is the main flavor of several fresh cheeses. At first, lactose
is hydrolyzed by starter cultures producing glucose and galactose. The former is then oxidized to
pyruvate by the Emden-Meyerhof pathway of glycolysis, while the latter is converted by galactosepositive bacteria and leuconostocs through the Leloir pathway to glucose-6-phosphate, and to
glyceraldehyde-6-phosphate by lactococci through the tagatose pathway (refer to Figure 12.2).
The intermediate pyruvate can also be converted to various short-chain flavor compounds, such
as diacetyl, acetoin, acetaldehyde, ethanol, and acetate. Diacethyl imparts a buttery, nutty flavor
Flavor Formation
283
Milk
Lactose
Citrate
Glucose
Galactose
Glucose-6-P
Tagatose-6-P
Glyceraldehyde-3-P
Oxaloacetate
Dihydroxyacetone-P
Pyruvate
Acetaldehyde Acetate
Ethanol
Figure 12.2
Diacetyl
Acetoin
and is considered to be significant for the flavor of Camembert [7,32], Cheddar [33,34], Emmental
[35], and cottage cheeses [36], while acetoin was considered to contribute to the flavors of Cheddar
[34] and Mozzarella cheeses [11] with a sour milk-resembling odor. Moreover, acetaldehyde was
described to impart a green note to Camembert [7,32] and Gruyre [37].
In addition, other starter organisms, such as heterofermentative starters, present the ability
to ferment other noncarbohydrate substrates, such as citrate, producing acetaldehyde, ethanol,
butan-1,2-diol, and diacetyl, yielding a more buttery flavor [36]. In citrate-utilizing LABs this
substrate is initially cleaved to oxaloacetate and acetate by a citrate lyase. Moreover, in cultures
of Lactococcus and Leuconostoc spp. oxaloacetate is decarboxylated to pyruvate. Two molecules of
the latter are then condensed by an -acetolactate synthase, forming -acetolactate and carbon
dioxide. The former is unstable, and its decarboxylation may be oxidative yielding diacetyl or nonoxidative forming acetoin, while the latter is responsible for the eye formation in some semihard
cheeses [38]. It should be noted that the initial breakdown of citrate and the further conversion
of the intermediate pyruvate into specific fermentation products can be regulated at different
levels, according to the microorganism. As aforementioned, heterofermentative starters produce
carbon dioxide that promotes an open texture. The use of Propionibacterium freudenreichii subsp.
shermanii, which ferments lactose, producing propionic acid and carbon dioxide is also noteworthy; the former contributes to the characteristic flavor of Swiss-type cheese, while the latter is, as
mentioned earlier, responsible for the eye formation in the cheese [39].
Nonstarter organisms may also ferment lactose producing a variety of compounds; the coliform fermentation generates formic acid, carbon dioxide, and hydrogen, the butyric fermentation
leads to butan-1-ol, butyric acid, acetone, propan-2-ol, and carbon dioxide formation, and the
ethanolic fermentation pathway generates ethanol and carbon dioxide. When the lactose supply is
depleted, and pH, water acidity, and reducing potential are not optimal, surviving homofermentative starters may widen their range of fermentative activity. Moreover, the lactose depletion rate
varies according to the cheese type; from 24 h in Swiss-type to 20 days in Cheddar cheese [40].
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12.3.2
The important raw materials for cheese flavor generation include not only low-molecular weight
compounds, as citrate and lactose, but also high-molecular weight proteins from which many of the
most important flavor compounds are derived, especially in hard-type and semihard-type cheeses.
The proteolytic process is initiated by the conversion of casein to large peptides by proteases.
Commonly, LAB strains produce a series of peptidases, which are able to further degrade large
peptides to smaller oligopeptides and amino acids. These, on their own, contribute to the flavor
promoting a sweet or brothy note. On the other hand, peptides with an undesired bitter taste may
also accumulate to concentrations higher than their threshold, which may be removed by the addition of adjuncts able to reduce bitterness, the so-called debittering peptidases [41]. Furthermore,
amino acid convertases trigger the formation of flavor compounds from amino acids, yielding
various alcohols, aldehydes, acids, esters, and sulfur compounds.
In the past, proteolysis was considered as a rate-limiting process in the maturation of many
cheeses, especially in semihard cheeses. However, it was demonstrated that enhancing the free
amino acid release by intensifying peptidolysis by LAB [42] or adding free amino acids did not
affect aroma formation in cheese [43], suggesting that the rate-limiting factor was not the release
of free amino acids but their conversion to flavor compounds.
In general, proteolysis proceeds at a slower rate especially in cheeses that are low in moisture or
have a rich salt content; both these characteristics are considered to control the maturation rate. In
addition, the concentration of free amino acids was found to be closely linked to the maturity of
cheeses, and was recognized as cheese flavor precursors. Amino acids are substrates for transamination, dehydrogenation, decarboxylation, and reduction, producing a wide variety of flavor compounds, or further precursors, such as amines and Strecker aldehydes (see Figure 12.3). The ability
Milk
Casein
Protease
Peptides
Peptidase
Amino acids
Aminotransferase
Deiminase
decarboxylase
Aldolases
Amines
Hydroxyacid
dehydrogenase
-Keto acids
Hydroxy acids
Alcohol dehydrogenase
Aldehydes
-keto acid
dehydrogenase
Aldehydes
lyases
Thiols
lyases
Sulfur-compounds
(methanethiol)
Phenol
Indole
Carboxylic acids
Alcohols
Thio-esters
(Thiols) Acyltransferases/
Acyltransferases/
esterases
esterases
Figure 12.3 Overview of protein metabolic pathways involved in the flavor formation of fermented dairy products.
Flavor Formation
285
12.3.2.2
The degradation of aromatic amino acids is initiated with a transamination step catalyzed by aminotransferases producing indole pyruvate, phenyl pyruvate, and p-hydroxy-phenyl pyruvate from
tryptophan, phenylalanine, and tyrosine, respectively.
Elimination reactions catalyzed by amino acid lyases may also be observed when yeast, micrococci, and Brevibacterium linens are used. These lyases are able to cleave the side chain of tyrosine
286
and tryptophan, yielding in a single-step phenol and indole, respectively. Moreover, this pathway
has not been detected in any LAB [50], though several of them are known to yield tyramine and
tryptamine by means of enzymatic decarboxylation of tyrosine and tryptophan.
Generally, compounds derived from aromatic amino acids are responsible for the impact flavor
of diverse cheeses; common flavor compounds are benzaldehyde (bitter almond resembling odor),
phenyl acetaldehyde (honey-like, floral, rosy, violet-like note), phenyl ethanol (floral, rosy, violetlike odor), phenyl acetate (honey-like note), and phenyl propanoate (floral), while less pleasant
notes are indole and skatole, both eliciting fecal putrid, musty odor at higher dilution, and p-cresol
(phenolic, medicinal flavor). Phenyl acetaldehyde, for instance, is of importance for the impact flavor of Gruyre [37,51] and bovine Mozzarella cheeses [49], while phenyl ethanol apart from being
one of the major volatile compounds identified in Camembert [52], is also commonly detected in
soft smear cheeses [53] and was already identified in Gruyre cheese [37].
Flavor Formation
287
Milk
Triglycerides
Lipase
Free fatty acids
-Oxidation
-Keto acids
-Oxidation
4-or 5-Hydroxyacids
-Ketoacyldecarboxylase
Methyl ketones
-or -Lactone
Redutase
Hydroperoxide lyase
Aldehydes
Secondary alcohols
Acids
Alcohols
Figure 12.4 Lipid catabolism pathways of some microorganisms utilized in the flavor formation
of fermented dairy products.
then oxidized to -ketoacids, which are decarboxylated to alkan-2-ones, and the latter undergoes
reduction yielding alkan-2-ol. Furthermore, mold cultures can also produce methyl ketones using
ketoacids naturally occurring in milk at low concentrations as substrate or by the oxidation of
monounsaturated fatty acids.
Methyl ketones are important flavor compounds, contributing particularly to the flavor of
Blue cheese [56], with their concentration increasing until the 70th day of ripening, then decreasing substantially; similar was observed for Emmental cheese [57]. Studies performed on Camembert cheese led to the identification of 11 methyl ketones; out of these, especially, 2-nonanone
(fatty, green note), 2-heptanone (fruity, fatty flavor), and 2-undecanone (herbaceous, fresh note)
increased in concentration throughout the ripening process [52]. The ketone 2-heptanone has also
been considered of importance for the flavor of Parmigiano Reggiano cheese, when present in
concentrations above its sensory threshold [58], as also for Emmental [35] and natural and creamy
Gorgonzola cheeses [59]. Another predominant methyl ketone in natural Gorgonzola [59] is also
2-nonanone. Besides, in full-fat Cheddar cheese, the concentrations of 2-heptanone, 2-nonanone,
and 2-undecanone increased until about 3.5 months of ripening and then decreased, while in lowfat Cheddar types the concentration of methyl ketones are drastically lower [60].
Esters are further products of the fatty acid catabolism, and are formed by reactions between
short- and medium-chain fatty acids with alcohols derived from lactose fermentation or from
amino acid catabolism. A great variety of esters, imparting fruity flavors, were identified in diverse
cheese types. Imhof and Bosset [31] investigated the flavor of Emmental cheese identifying 14
esters, and Meinhart and Schreier [61] detected 38 esters in Parmigiano Reggiano cheese, with
ethyl ethanoate, ethyl octanoate, ethyl decanoate, and methyl hexanoate as the most abundant
ones. Thioesters formed by the reaction of esters of short-chain fatty acids with methional imparted
288
the characteristic cheese-like aroma to Cheddar cheese [34], while S-methyl thioesters contribute
with a characteristic strong flavor to various smear-ripened soft cheeses, such as Limburger and
Havarti [62].
Lactones occur naturally in milk, and also in cheeses, but are not considered to be of great relevance to the flavor of cheeses. In Parmigiano Reggiano cheese, for instance, diverse lactones were
detected, -octalactone being the most significant molecule [61], while Camembert flavor comprised -decalactone, -decalactone, -dodecalactone, and -dodecalactone [63]. Moreover, the
commonly detected -decalactone is one of the most important lactones not only for the flavor of
Camembert, as also for the one of Emmental [47] and Blue cheeses [63]. On the other hand, British farmhouse Cheddar cheese flavor is characterized by the presence of -dodecalactone [64].
Aldehydes may also be detected in several cheese types, such as straight-chain aldehydes,
specially n-nonanal, characterized by a green grassy odor in water buffalo Mozzarella cheese [49].
Most commonly aldehydes are transitory compounds, which rapidly reduce to primary alcohols or
oxidize into the corresponding acids. In addition, the enzymatic reduction of methyl ketones may
yield secondary alcohols; such as 2-propanol and 2-butanol in Cheddar cheese due to reduction
of acetone and butanone, respectively [65], or 2-heptanol and 2-nonanol in mold-ripened cheeses,
e.g., Camembert [52], Brie [66], and Blue cheeses [63].
12.4
Concluding Remarks
It is widely agreed that a single volatile compound does not elicit the characteristic flavor of a dairy
product. Furthermore, it is important to outline that synergistic or suppressive effects of different
flavors present in a dairy food matrix should be taken into consideration. The characteristic flavor
of a cheese is defined by the so-called component balance theory [28], which is ruled by a wide
range of parameters, such as cheese age, microflora, and biochemistry.
Dairy product development is nowadays directed toward new items with distinct flavors. In
many cases, this requires the development of special starter cultures delivering specific flavor compounds in a selected product. It is worthwhile to highlight that the presence of starter cultures is
not sufficient to explain flavor formation in raw milk cheeses and their selection has never been
made with respect to the flavor criterion. Starter cultures metabolic pathways have been exploited
to increase knowledge on dairy food flavor formation, and at present, diverse metabolic engineering strategies are reported providing solutions, such as metabolic interventions in Lactococcus lactis
and other LAB improving the flavor of fermented foods. Several authors make reference to the use
of tailor-made mixed cultures of known species of bacteria to provide specific dairy flavors.
Moreover, the further growing demand for new flavor compounds triggers the development
and application of analytical methodologies, which are exhaustively described in Chapter 38. As is
well known, the complexity of the samples that are analyzed typically mandates that some type of
separation be achieved before the component analytes can be measured and characterized, in this
respect the utilization of gas chromatography and mass spectrometry is widely diffused.
References
1. Friedrich, J. E. and Acree, T. E., Gas chromatography olfactometry (GC/O) of dairy products, Int.
Dairy J., 8, 235, 1998.
2. Smit, G., Smit, B. A., and Engels, W. J. M., Flavour formation by lactic acid bacteria and biochemical
flavour profiling of cheese products, FEMS Microbiol. Rev., 29, 591, 2005.
Flavor Formation
289
3. Marilley, L. and Casey, M. G., Flavours of cheese products: Metabolic pathways, analytical tools and
identification of producing strains, Int. J. Food Microbiol., 90, 139, 2004.
4. Patton, S., The isolation of Maltol from heated skim milk, J. Dairy Sci., 33, 102, 1950.
5. Patton, S., Studies of heated milk. III. Mode of formation of certain furan compounds, J. Dairy Sci.,
33, 904, 1950.
6. Christensen, K. R. and Reineccius, G. A., Aroma extract dilution analysis of aged Cheddar cheese,
J. Food Sci., 60, 218, 1995.
7. Kubkov, J. and Grosch, W., Evaluation of potent odorants of Camembert cheese by dilution and
concentration techniques, Int. Dairy J., 7, 65, 1997.
8. Baigrie, B., Introduction, in Taints and Off-Flavours in Food, 1st edn., Baigrie, B., Ed., Woodhead
Publishing Ltd., Cambridge, MA, 2003, Chapter 1.
9. Adda, J., Flavour of dairy products, in Developments in Food Flavours, 1st edn., Birch, G. G. and
Lindley, M. G., Eds., Elsevier Applied Science, London, 1987, pp. 151172.
10. Shibamoto, T., Flavor volatiles formed by heated milk, in The Analysis and Control of Less Desirable
Flavors in Foods and Beverages, 1st edn., Charalambous, G., Ed., Academic Press, New York, 1980,
pp. 241265.
11. Moio, L. et al., Powerful odorants in bovine, ovine, caprine and water buff alo milk determined by
means of gas chromatographyolfactometry, J. Dairy Res., 60, 215, 1993.
12. Moio, L. et al., Detection of powerful odorants in heated milk by use of extract dilution sniffing
analysis, J. Dairy Res., 61, 385, 1994.
13. Moio, L. et al., Odorous constituents of ovine milk in relationship to diet, J. Dairy Sci., 79, 1322,
1996.
14. Ferretti, A. and Flanagan, V. P., The lactosecasein (Maillard) browning system: Volatile components, J. Agric. Food Chem., 19, 245, 1971.
15. Parks, O. W. and Patton, S., Volatile carbonyl compounds in stored dry whole milk, J. Dairy Sci., 44,
1, 1961.
16. Ramshaw, E. H. and Dunstone, E. A., Volatile compounds associated with the off-flavour in stored
casein, J. Dairy Sci., 36, 215, 1969.
17. Rijnen, L. et al., Lactococcal aminotransferases AraT and BcaT are key enzymes for the formation of
aroma compounds from amino acids in cheese, Int. Dairy J., 13, 805, 2003.
18. Dimick, P. S., Walker, N. J., and Patton, S., Occurrence and biochemical origin of aliphatic lactones
in milk fatA review, J. Agric. Food Chem., 17, 649, 1969.
19. Hutton, J. T. and Patton, S., The origin of sulfhydryl groups in milk proteins and their contribution
to cooked flavor, J. Dairy Sci., 35, 699, 1952.
20. Urbach, G., Headspace volatiles from cold-stored raw milk, Aust. J. Dairy. Technol., 45, 80, 1990.
21. Bekblet, M., Light effects on food, J. Food Prot., 53, 430, 1990.
22. Wishner, L. A., Light-induced oxidations in milk, J. Dairy Sci., 47, 216, 1964.
23. Allen, C. and Parks, O. W., Evidence for methional in skim milk exposed to sunlight, J. Dairy Sci.,
58, 1609, 1975.
24. Samuelsson, E. G., Model experiments on sunlight flavor in milk di- and tripeptides and methionine,
Int. Dairy Cong., A, 152, 1962.
25. Bills, D. D. et al., Effect of sucrose on the production of acetaldehyde and acids by yogurt culture
bacteria, J. Dairy Sci., 55, 1570, 1972.
26. Bodyfelt, F. W., Tobias, J., and Trout, G. M., The Sensory Evaluation of Dairy Products, Van Nostrand
Reinhold, New York, 1988.
27. van Aardt, M. et al., Flavor threshold for acetaldehyde in milk, chocolate milk, and spring water using
solid phase microextraction gas chromatography for quantification, J. Agric. Food Chem., 49, 1377,
2001.
28. Singh, T. K., Drake, M. A., and Cadwallader, K. R., Flavor of Cheddar cheese: A chemical and sensory perspective, Comp. Rev. Food Sci. Food Saf., 2, 165, 2003.
29. Hammes, W. P., Bacterial starter cultures in food production, Food Biotechnol., 4, 383, 1990.
290
30. Molimard, P. and Spinnler, H. E., Compounds involved in the flavour of surface mold-ripened
cheeses: Origins and properties, J. Dairy Sci., 79, 169, 1996.
31. Imhof, B. and Bosset, J. O., Relationship between microorganisms and formation of aroma compounds in fermented dairy products, Z. Lebensm. Unters. Forsch., 198, 267, 1994.
32. Kubkov, J. and Grosch, W., Evaluation of flavour compounds of Camembert cheese, Int. Dairy J.,
8, 11, 1998.
33. Milo, C. and Reineccius, A., Identification and quantification of potent odorants in regular-fat and
low-fat mild Cheddar cheese, J. Agric. Food Chem., 45, 3590, 1997.
34. Arora, G., Cormier, F., and Lee, B., Analysis of odor-active volatiles in Cheddar cheese headspace by
multidimensional GC/MS/sniffing, J. Agric. Food Chem., 43, 748, 1995.
35. Preininger, M., Rychlik, M., and Grosch, W., Potent odorants of the neutral volatile fraction of Swiss
cheese (Emmentaler), in Trends in Flavour Research, 1st edn., Maarse, H. and van der Heij, D. G.,
Eds., Elsevier, Amsterdam, 1994, pp. 267270.
36. Hugenholtz, J., Citrate metabolism in lactic acid bacteria, FEMS Microbiol. Rev., 12, 165, 1993.
37. Rychlik, M. and Bosset, J. O., Flavour and off-flavour compounds of Swiss Gruyre cheese. Evaluation of potent odorants, Int. Dairy J., 11, 895, 2001.
38. Boumerdassi, H. et al., Effect of citrate on production of diacetyl and acetoin by Lactococcus lactis ssp.
lactis CNRZ 483 cultivated in the presence of oxygen, J. Dairy Sci., 80, 634, 1997.
39. Vangtal, A. and Hammond, G., Correlation of the flavour characteristics of Swiss-type cheeses with
chemical parameters, J. Dairy Sci., 69, 2982, 1986.
40. Laht, T. et al., Role of arginine in the development of secondary microflora in Swiss-type cheese, Int.
Dairy J., 12, 831, 2002.
41. Sridhar, V. R. et al., Identification of endopeptidase genes from the genomic sequence of Lactobacillus
helveticus CNRZ32 and the role of these genes in hydrolysis of model bitter peptides, Appl. Environ.
Microbiol., 71, 3205, 2005.
42. Christensen, J. E., Johnson, M. E., and Steele, J. L., Production of Cheddar cheese using a Lactococcus
lactis ssp. cremoris SK11 derivative with enhanced aminopeptidase activity, Int. Dairy J., 5, 367, 1995.
43. Wallace, J. M. and Fox, P. F., Effect of adding free amino acids to Cheddar cheese curd on proteolysis,
flavour and texture development, Int. Dairy J., 7, 157, 1997.
44. Yvon, M. and Rijnen, L., Cheese flavour formation by amino acid catabolism, Int. Dairy J., 11, 185,
2001.
45. Bosset, J. O., Collomb, M., and Sieber, R., The aroma composition of Swiss Gruyre cheese IV.
The acidic volatile components and their changes in content during ripening, Lebensm. Wissenschaft
Technol., 26, 581, 1993.
46. Thierry, A. and Maillard, M. B., Production of cheese flavour compounds derived from amino acid
catabolism by Propionibacterium freudenreichii, Lait, 82, 17, 2002.
47. Preininger, M., Warmke, R., and Grosch, W., Identification of the character impact flavour compounds of Swiss cheese by sensory studies of models, Lebensm. Unters. Forsch., 202, 30, 1996.
48. Banks, J. M. et al., Enhancement of amino acid catabolism in Cheddar cheese using -ketoglutarate:
Amino acid degradation in relation to volatile compounds and aroma character, Int. Dairy J., 11, 235,
2001.
49. Moio, L. et al., Volatile flavour compounds of water buffalo Mozzarella cheese, Ital. J. Food Sci., 5, 57,
1993.
50. Gummala, S. and Broadbent, J. R., Tryptophan catabolism by Lactobacillus casei and Lactobacillus
helveticus cheese flavor adjuncts, J. Dairy Sci., 82, 2070, 1999.
51. Rychlik, M. and Bosset, J. O., Flavour and off-flavour compounds of Swiss Gruyre cheese. Identification of key odorants by quantitative instrumental and sensory studies, Int. Dairy J., 11, 903, 2001.
52. Dumont, J. P. et al., Etude des composs neutres volatils prsents dans le Camembert, Lait, 538, 501,
1974.
53. Sabl, S. and Cottenceau, G., Current knowledge of soft cheeses flavor and related compounds,
J. Agric. Food Chem., 47, 4825, 1999.
Flavor Formation
291
54. Gripon, J. C., Mould-ripened cheeses, in Cheese: Chemistry, Physics and Microbiology. 2. Major Cheese
Groups, 2nd edn., Fox, P. F., Ed., Elsevier, London, 1993, pp. 111136.
55. Bills, D. D. and Day, E. A., Determination of the major free fatty acids of Cheddar cheese, J. Dairy
Sci., 47, 733, 1964.
56. Dartley, C. K. and Kinsella, J. E., Rate of formation of methyl ketones during Blue cheese ripening,
J. Agric. Food Chem., 19, 771, 1971.
57. Thierry, A., Maillard, M. B., and Le Quere, J. L., Dynamic headspace analysis of Emmental aqueous
phase as a method to quantify changes in volatile flavour compounds during ripening, Int. Dairy J.,
9, 453, 1999.
58. Qian, M. and Reineccius, G., Potent aroma compounds in Parmigiano Reggiano cheese studied using
a dynamic headspace (purge-trap) method, Flavour Fragr. J., 18, 252, 2003.
59. Moio, L., Piombino, P., and Addeo, F., Odour-impact compounds in Gorgonzola cheese, J. Dairy
Res., 67, 273, 2000.
60. Dimos, A., Urbach, G. E., and Miller, A. J., Changes in flavour and volatiles of full-fat and reducedfat Cheddar cheeses during maturation, Int. Dairy J., 6, 981, 1996.
61. Meinhart, E. and Schreier, P., Study of flavour compounds from Parmigiano Reggiano cheese,
Milchwissenschaft, 41, 689, 1986.
62. Lamberet, G., Auberger, B., and Bergere, J. L., Aptitude of cheese bacteria for volatile S-methyl
thioester synthesis. II. Comparison of coryneform bacteria, Micrococcaceae and some lactic acid
bacteria starters, Appl. Microbiol. Biotechnol., 48, 393, 1997.
63. Gallois, A. and Langlois, D., New results in the volatile odorous compounds of French cheese, Le Lait,
70, 89, 1990.
64. Suriyaphan, O. et al., Characteristic aroma components of British Farmhouse Cheddar cheese,
J. Agric. Food Chem., 49, 1382, 2001.
65. Urbach, G., Relations between cheese flavour and chemical composition, Int. Dairy J., 3, 389, 1993.
66. Karahadian, C., Josephson, D. B., and Lindsay, R. C., Contribution of Penicillium sp. to the flavors
of Brie and Camembert cheese, J. Dairy Sci., 68, 1865, 1985.