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Volatile Flavor Compounds in Yogurt: A Review: Hefa Cheng
Volatile Flavor Compounds in Yogurt: A Review: Hefa Cheng
State Key Laboratory of Organic Geochemistry, Guangzhou Institute of Geochemistry, Chinese Academy of Sciences,
Guangzhou, China
Considerable knowledge has been accumulated on the volatile compounds contributing to the aroma and flavor of yogurt.
This review outlines the production of the major flavor compounds in yogurt fermentation and the analysis techniques, both
instrumental and sensory, for quantifying the volatile compounds in yogurt. The volatile compounds that have been identified
in plain yogurt are summarized, with the few key aroma compounds described in detail. Most flavor compounds in yogurt
are produced from lipolysis of milkfat and microbiological transformations of lactose and citrate. More than 100 volatiles,
including carbonyl compounds, alcohols, acids, esters, hydrocarbons, aromatic compounds, sulfur-containing compounds,
and heterocyclic compounds, are found in yogurt at low to trace concentrations. Besides lactic acid, acetaldehyde, diacetyl,
acetoin, acetone, and 2-butanone contribute most to the typical aroma and flavor of yogurt. Extended storage of yogurt
causes off-flavor development, which is mainly attributed to the production of undesired aldehydes and fatty acids during
lipid oxidation. Further work on studying the volatile flavor compounds-matrix interactions, flavor release mechanisms,
and the synergistic effect of flavor compounds, and on correlating the sensory properties of yogurt with the compositions of
volatile flavor compounds are needed to fully elucidate yogurt aroma and flavor.
Keywords
INTRODUCTION
Yogurt is a cultured dairy product that is widely consumed
as a healthy and nutritious food and for its sensory properties.
Chemically, yogurt is a complex gel system incorporating protein, polysaccharide, and lipids in its structure. It is produced
from milk by fermentation, one of the oldest methods practiced
by human beings for the transformation of milk into products
with an extended shelf life (Tamime and Robinson, 1999). Yogurt was likely first discovered by the nomadic people living in
the Middle East, and it has been consumed for thousands of years
by different civilizations. Today, yogurt is commonly made by
fermenting cows milk using a symbiotic culture of the bacteria Lactobacillus bulgaricus and Streptococcus thermophilus
under controlled temperatures and environmental conditions, especially in industrial production (Marshall, 1993; Tamime and
Robinson, 1999). Fermentation of the milk sugar (lactose) produces lactic acid, which denatures milk protein to give yogurt its
texture (through formation of the coagulated gel) and its char-
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YOGURT VOLATILES
Table 1
Carbonyl compounds
Acetaldehyde
Acetone
Propanal
2-Propanone
Butanal
2-Butanone
Diacetyl
Acetoin
Pentanal
2-Methylbutanal
3-Methylbutanal
3-Methyl-2-butenal
2-Pentanone
3-Penten-2-one
2-Hydroxy-3-pentanone
2,3-Pentanedione
Hexanal
2-Hexanone
3-Hexanone
Heptanal
2-Heptanone
3-Heptanone
Octanal
3-Octanone
1-Octen-3-one
1-Nonen-3-one
Nonanal
(E)-2-Nonenal
2-Nonanone
Decanal
Undecanal
2-Undecanone
2-Dodecanone
2-Pentadecanone
-Dodecalactone
-Dodecalactone
Benzaldehyde
Phenylacetaldehyde
Alcohols
Methanol
Ethanol
1-Propanol
2-Propanol
1-Butanol
2-Butanol
2-Methyl-1-propanol
Cyclobutanol
1-Pentanol
3-Pentanol
1-Penten-3-ol
3-Methyl-2-butenol
3-Methylbutanol
Pentan-2-one-4-ol
3-Methyl 3-cyclohexenol
2-Ethyl hexanol
2-Buthyl octanol
Guaiacol
Acids
Acetic acid
Propionic acid
Butyric acid
2-Methylpropanoic acid
Pentanoic acid
Isovaleric acid
Hexanoic acid
Heptanoic acid
Octanoic acid
Nonanoic acid
Decanoic acid
Benzoic acid
Esters
Methyl formate
Methyl acetate
Ethyl acetate
Butyl acetate
Diehyl phthalate
Sulfur compounds
Dimethyl sulfide
Dimethyl disulfide
Dimethyl trisulfide
S-methyl thioacetate
Methional
Tetramethyl thiourea
Nitrogen compounds
N,N-dimethylformamide
Lactamide
N-ethyl-benzenamine
Hydrocarbons
Heptane
Methylcyclohexane
Nonane
Undecane
Aromatic compounds
Benzene
Toluene
Ethylbenzene
1,3-Dimethylbenzene
1,4-Dimethylbenzene
1,2-Dimethylbenzene
Ethenylbenzene
Propylbenzene
Trimethylbenzene
1-Methyl ethenylbenzene
1-Ethyl-4-methylbenzene
Heterocyclic compounds
Furan
Furfural
2-Methylfuran
2-Pentylfuran
2-Furanmethanol
Pyrazine
Methylpyrazine
Pyrrole
1-Methylpyrrole
2-Methyl tetrahydrofuran-3-one
2-Methylthiophene
2-Methyltetrahydrothiophen-3-one
Benzothiazole
Methyl 2-piperidine
Furfuralcohol
1,2-Dihydro-2,2,4-Trimethylquinoline
2,3-dihidro-1,3,3-trimethyl 1H-Indole
Terpene
L-limonene
Otherssolvent contamination?
Acetonitrile
Dichlorometane
Trichloromethane
Sources: Beshkova et al. 1998, Guler 2007, Imhof and Bosset, 1994b, Laye et al., 1993, and Ott et al., 1997.
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H. CHENG
Triglyceride
Lipase
Fatty acids
-oxidation,
-oxidation
Oxidation
-2H2 + H2O
Hydroperoxides
4- or 5-Hydroxyacids
Thiohydrolase
Ring closure,
Hydroperoxidelase
-H2O
- and - Lactones
Aldehydes
Oxidation
Acids
CO2
Reduction
Alcohols
Reductase
Note:
Secondary alcohol
Figure 1
General degradation pathways of milkfat during milk fermentation (modified from Fox and McSweeney, 1998 and McSweeney and Sousa, 2000).
941
YOGURT VOLATILES
Lactose
(a)
Galactose
Glucose
ATP
ATP
ADP
ADP
Glucose-1-phosphate
Glucose-6-phosphate
Fructose-6-phosphate
P
Homolactic fermentation
Heterolactic fermentation
Fructose-1,6-biphosphate
Acetyl phosphate
Erythrose-4-phosphate
ADP
Dihydroxyacetone phosphate
Glycemldehyde-3-phosphate
ATP
4 ADP
Acetate
4 ATP
2 NAD+
2 Glycemldehyde-3-phosphate
2 NADH
2 Acetyl phosphate
2 ADP
4 ADP
Pyruvate
4 ATP
2 NADH
2 ATP
2 NAD+
2 NAD
2 Acetate
2 NADH
Lactate
2 Pyruvate
Notes:
2 NADH
ATP: adenosine-5'-triphosphate
2 NAD+
2 Lactate
Lactate
(b)
NADH
NAD+
Puryvate
CoA
NAD+
Pyruvate
Pyruvate
formate-lyase
dehydrogenase
NADH
Formate
CO2
Acetyl-CoA
NADH
P
NAD+
CoA
CoA
Acetaldehyde
Acetylphosphate
NADH
ADP
NAD+
ATP
Ethanol
Acetate
Notes:
CoA: coenzyme A
ATP: adenosine-5'-triphosphate
ADP: adenosine diphosphate
NAD+ (oxidized form) and NADH (reduced form): nicotinamide adenine dinucleotide
Figure 2 General degradation pathways of lactose and lactate during milk fermentation: (a) homolactic and heterolactic fermentation of lactose (modified from
Fox and McSweeney, 1998 and Tamime and Robinson, 1999), and (b) metabolic pathways of lactate (modified from McSweeney and Sousa, 2000).
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H. CHENG
Citrate
Citrate lyase
Acetate
Oxalacetate
Oxalacetate
NAD+
decarboxylase
CO2
NADH
TPP
CO2
Puryvate
Lactate
Acetaldehyde-TPP
Lactate Dehydrogenase
Acetyl CoA
Acetolactate
synthase
Diacetyl
synthase
CoA-SH
-Acetolactate
Acetolactate
decarboxylase
2,3-Butanediol
Acetoin reductase
NAD(P)+
CO2
Acetoin
NAD(P)H
TPP
CO2
Oxidative
decarboxylation
Diacetyl reductase
NAD(P)+
Diacetyl
NAD(P)H
Notes:
CoA or CoA-SH: coenzyme A
TPP: thiamine pyrophosphate
NAD+ (oxidized form) and NADH (reduced form): nicotinamide adenine dinucleotide
NADP+ (oxidized form) and NADPH (reduced form): nicotinamide adenine dinucleotide phosphate
Figure 3
General metabolic pathways of citrate during milk fermentation (modified from Fox and McSweeney, 1998 and McSweeney and Sousa, 2000).
concentrations (g/kg to mg/kg range) in yogurt (CarrilloCarriona et al., 2007; Friedrich and Acree, 1998; Mariaca
and Bosset, 1997; McGorrin, 2001), isolation of volatiles
from complex matrix and enrichment are often necessary for
their analyses. Unfortunately, the extraction and concentration
of volatile flavor components from dairy products, prior to
their analysis, poses a major analytical challenge. The main
problems encountered during this process are:
(i) tendency of the compounds to degrade or to form artifacts
in the presence of heat and/or oxygen;
(ii) potential formation of secondary volatiles via enzymatic
reactions; and
(iii) incomplete recovery of the polar/semi-volatile flavor constituents (Mariaca and Bosset, 1997; McGorrin, 2001).
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YOGURT VOLATILES
Table 2
Comparison of different preconcentration and enrichment techniques used for analyzing volatile compounds in yogurt and other cultured dairy products
Technique
Principle
Advantages
Limitations
Static headspace
concentration
Dynamic headspace
concentration/purge
and trap
Simultaneous steam
distillation/solvent
extraction
Steam distillation
High-vacuum distillation
Molecular distillation
Direct extraction
Dialysis
Solid phase
microextraction
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Table 3
H. CHENG
Compound
Carbonyl compounds
Acetaldehyde:
Acetone
2-Propanone
2-Butanone
Diacetyl
Acetoin
3-Methyl-2-butenal
2-Pentanone
3-Methylbutanal
2,3-pentanedione
Hexanal
2-Hexanone
Heptanal
Nonanal
2-Nonanone
2-Pentanone
Heptanone
3-Octanone
1-Octen-3-one
Nonanone
2-Undecanone
g-Dodecalactone
d-Dodecalactone
2-Phenylacetaldehyde
Alcohols
Ethanol
1-Pentanol
2-Heptanol
1-Octen-3-ol
Octan-2-ol
Oct-1-en-3-ol
Guaiacol
Esters
Ethyl acetate
Ethyl butanoate
Ethyl hexanoate
Ethyl octanoate
Butyl acetate
Acids
Acetic acid
Propionic acid
Butyric acid
Isobutyric acid
Isovaleric acid
Hexanoic acid
Octanoic acid
Decanoic acid
Sulfur compounds
Dimethyl sulfide
Dimethyl disulfide
Dimethyl trisulfide:
Methional
S-methyl thioacetate
Notes:
a.Friedrich and Acree, 1998;
b.Ott et al., 1997;
c.Molimard and Spinnler, 1996;
d.Mariaca et al., 2001.
Descriptor
Ethereal, fresh, green, pungent
Sweet, fruity
Sweet, fruity
Varnish-like, sweet, fruity
Buttery, creamy, vanilla
Buttery
Metallic, aldehydic, herbaceous
Fruity, acetone
Green, malty, unripe, cocoa, malty
Butter, vanilla, mild
Green, cut-grass
Floral, fruity
Green, sweet
Sweet, floral, citrus, grass-like
Fruity, musty
Sweet, fruity, cheesy
Fruity, spicy, cinnamon
Mushroom, fruity
Mushroom-like, earthy, fruity
Grassy-herbal, green-fruity, floral
Floral, rose-like, herbaceous
Fresh fruit, peach, par, plum, coconut, buttery
Peach, coconut, buttery, musky
Flowery
Mild, ether
Alcoholic, iodoform-like
Earthy, oily
Mushroom-like
Green
Mushroom
Bacon, phenolic, smoked, spicy
Solvent-like, fruity, pineapple
Fruity, sweet, banana
Fruity, apple, banana
Fruity, banana, apple
Pineapple
Reference
a, b, d
c
c
c, d
a, b, c, d
c, d
b
c
a, d
b
a, d
c
a, d
a, d
c
d
a, d
c
a, b, c
a, d
a, c
c
a, c
b
c
d
d
a
c
c
b
c, d
a, d
d
a, d
c
a, b, c
a, c
a, c
c
a, b, c
a, b, c
c, d
b
a, b, c
C
b, c
c
c
YOGURT VOLATILES
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946
H. CHENG
2,3-pentanedione, methional, 2-methyltetrahydrothiophene-3one, (E)-2-nonanal, 3-methylbutyric acid, guiacol, benzothiazole and two unidentified compounds (Ott et al., 1997). Imhof
and co-workers (1994; 1995) determined the key aroma components in Switzerland yogurt based on the ratio between the concentration of the volatile in the product and its threshold concentration and identified six volatiles (acetaldehyde, dimethylsulphide, diacetyl, 2,3-pentanedione, L-limonene, and undecanal)
as having high impact. However, these results should be interpreted with caution because the odor threshold values of the
volatiles are usually determined in water instead of dairy products. The main ingredients (fat, proteins, and carbohydrates) in
yogurt can significantly reduce the actual release of volatiles
(Brauss et al., 1999; Fares et al., 1998; Roberts and Pollien,
2000).
Carbonyl Compounds
Carbonyl compounds comprise the main aromatic substances
in yogurt, among which acetaldehyde is the compound that
contributes most to the typical flavor of yogurt (Bottazzi and
Dellaglio, 1967; Gaafar, 1992; Law, 1981; Ott et al., 1997;
Pourahmad and Assadi, 2005). Pure acetaldehyde possesses a
pungent irritating odor but at dilute concentrations it gives a
pleasant fruity aroma. Acetaldehyde imparts yogurt its characteristic green apple or nutty flavor, and both Lactobacillus
bulgaricus and Streptococcus thermophilus readily produce it
(Bodyfelt et al., 1988). Acetaldehyde is an indispensable aroma
compound in yogurt; good flavored yogurt results when proper
levels (2340 mg/kg and at least 810 mg/kg) of acetaldehyde
are produced (Gaafar, 1992; Georgala et al., 1995; Kang et al.,
1988; Kneifel et al., 1992; Rasic and Kurmann, 1978).
Diacetyl is an important aroma compound that gives the buttery flavor and it may improve yogurt flavor quality at elevated
concentrations. Diacetyl reportedly contributes to the delicate,
full flavor and aroma of yogurt and is especially important for
products that contain low acetaldehyde concentrations (Groux,
1973). Diacetyl is a diketone, derived by the fermentation of citrate present in milk and dairy mixes (Vedamuthu, 2006). Small
quantities of diacetyl, ranging from traces to 0.90 mg/kg or more
contribute to the pleasant and delicate flavor and aroma of yogurt (Rasic and Kurmann, 1978). The typical concentrations of
diacetyl in yogurt ranged from 0.2 mg/kg to 3 mg/kg (Georgala
et al., 1995; Hernandez et al., 1995; Kang et al., 1988; Marshall,
1984; Pourahmad and Assadi, 2005; Rysstad and Abrahamsen,
1987; Ulberth, 1991). There are differing views on the role of
diacetyl in the formation of yogurt flavorsome researchers
regard it as a dominating flavor component only when acetaldehyde contents are low (Groux, 1973; Rysstad and Abrahamsen,
1987), while others attribute to it the leading role in flavor formation (Imhof et al., 1994; Kneifel et al., 1992).
Acetoin is a common flavor substance in many cultured dairy
products. Acetoin has a mild creamy, slightly sweet, butter-like
flavor that is similar to that of diacetyl. Meanwhile, the flavor of
acetoin is considerably weaker than that of diacetyl and it tends
YOGURT VOLATILES
947
age time. Most esters have a fruity and floral flavor and may
contribute to the aroma and flavor by minimizing the sharpness
and bitterness imparted by fatty acids and amines (Guler, 2007;
Molimard and Spinnler, 1996).
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H. CHENG
CONCLUSIONS
Advances made on characterizing the volatile aroma compounds in yogurt provide a basis for improving the quality
of yogurt and quality control during production and storage.
More than 100 volatile compounds have been identified in yogurt, among which acetaldehyde, diacetyl, acetoin, acetone, 2butanone, play the most important role in imparting the typical
aroma and flavor. Formation of undesired aldehydes and fatty
acids during lipid oxidation causes off-flavor development during extended storage of yogurt. Much work remains to be done
to gain a more complete understanding of the formation of the
aroma and flavor of yogurt. Qualitative and quantitative analysis
of the volatile flavor compounds is only the first step towards
achieving this goal. Quantifying the volatile compounds-matrix
interactions, the release mechanisms of volatile compounds, and
their synergistic actions are necessary to accurately assess their
aromatic contributions. Determining the relationship between
key aroma compounds and the sensory properties of yogurt will
provide a better understanding on how yogurt flavor is affected
by the presence of critical aroma compounds and facilitate the
production of more uniform yogurt products with greater consumer acceptance.
YOGURT VOLATILES
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