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Processing and Storage Effects on Orange Juice Aroma: A Review

Article  in  Journal of Agricultural and Food Chemistry · November 2008

DOI: 10.1021/jf801244j · Source: PubMed

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 J. Agric. Food Chem. 2008, 56, 9785–9796 9785

REVIEW

Processing and Storage Effects on Orange Juice

Aroma: A Review
PILAR RUIZ PEREZ-CACHO†,‡ AND RUSSELL ROUSEFF*,†
University of Florida, Institute of Food and Agricultural Sciences, Citrus Research and Education
Center, 700 Experiment Station Road, Lake Alfred, Florida 33850, and IFAPA, Centro Alameda del
Obispo, Av. Menéndez Pidal s/n, 14080-Cordoba, Spain

Freshly squeezed orange juice aroma is due to a complex mixture of volatile compounds as it lacks
a specific character impact compound. Fresh hand-extracted juice is unstable, and thermal processing
is required to reduce enzyme and microbial activity. Heating protocols range from the lightly heated
not from concentrate, NFC, to the twice heated, reconstituted from concentrate, RFC, juices. Thermal
processing profoundly effects aroma composition. Aroma volatiles are further altered by subsequent
time-temperature storage conditions. Heating reduces levels of reactive aroma impact compounds
such as neral and geranial, and creates off-flavors or their precursors from Maillard, Strecker, and
acid catalyzed hydration reactions. Off-flavors such as 4-vinylguaiacol, p-cymene, and carvone are
the products of chemical reactions. Other off-flavors such as butane-2,3-dione, guaiacol, and 2,6-
dichlorophenol are indicators of microbial contaminations. Since most orange juice consumed
worldwide is processed, the goal of this review is to summarize the widely scattered reports on orange
juice aroma differences in the three major juice products and subsequent aroma changes due to
packaging, storage, and microbial contamination with special emphasis on results from GC-O studies.

KEYWORDS: Citrus; fruit juices; aroma-active compounds; odor volatiles; off-flavors; gas chromatography-
olfactometry; thermal degradation products; packaging

INTRODUCTION thermal processing will reduce concentrations of some of the

original juice volatiles as well as induce a complex series of
Orange juice is the most widely consumed fruit juice in the
chemical reactions that can ultimately produce odors foreign
world. However, not all orange juices taste alike. The pleasant
to freshly expressed juice (1). Other orange juice processing
odor of freshly squeezed orange juice is distinctly different from
steps can alter juice flavor. One of the major quality variables
that of many commercial juices. There is also a wide flavor
of commercial juice is the mechanical pressure used to extract
range among the various types of commercial orange juice.
the juice from the fruit. High extraction pressure (hard squeeze)
Differences between commercially processed juices are due to
will produce high juice yields. Lower extraction pressure (soft
the combined effects of fruit cultivar and maturity, time-tem-
squeeze) will produce less juice, but the juice will be more
perature conditions used to stabilize the juice, the number of
similar to the flavor of hand extracted juice. Extraction condi-
times it has been heated, whether the juice has been concen-
tions will determine relative levels of juice and peel components
trated, and if concentrated, how well the volatiles lost during
and, therefore, the final flavor of the juice. The pressure used
concentration have been restored. In addition, storage time-tem-
perature conditions and container type can have a profound to separate the juice from the pulp (finisher pressure) will also
impact on juice flavor at the time of consumption. Although alter the composition of the juice. Depulping can reduce some
alternate processes have been developed, almost all com- of the volatiles associated with the pulp, thus altering its flavor
mercially produced orange juice is thermally processed because (2). Deaeration is one of the final steps applied before
thermal processing is still the most cost-effective means to pasteurization and can alter orange juice volatile composition
reduce microbial populations and enzyme activity. However, by pulling off some of the most volatile juice components along
with entrained air.
* Corresponding author. Tel: 863 956 1151, ext. 1477. Fax: 863 956
Packaging materials, storage time-temperature conditions,
4631. E-mail: rrouseff@ufl.edu. and microbial contamination can also profoundly alter juice
†
University of Florida. flavor. Juice aroma compounds can be absorbed by polymeric
‡
Centro Alameda del Obispo. packaging materials (3-5), and some taints can migrate from
10.1021/jf801244j CCC: $40.75  2008 American Chemical Society
Published on Web 10/02/2008
9786 J. Agric. Food Chem., Vol. 56, No. 21, 2008 Review

the packaging materials into the juice (6). Storage time and chemical mixture contains many compounds previously sepa-
temperature can also alter juice aroma profiles due to Maillard, rated within the intact fruit but are now free to interact. In
Strecker, and acid catalyzed hydration reactions. The formation addition, peel oil from the flavedo is commingled with the juice
of methional from methionine is probably the most significant when the peel is broken during juice extraction. The juice also
example of Strecker degradation in orange juice. Furthermore, contains a native amount of oil, which is slightly different in
microbiological contaminations can alter the characteristic aroma composition than that from peel (flavedo). Therefore, the type
of orange juices or produce specific off-flavors, producing of commercial extractor and extractor pressures will determine
consumer complaints and product rejection (7). the relative levels of peel versus juice oils and the composition
Consumers demand juice products with characteristics similar of the juice volatiles, and, therefore, the overall flavor of the
to those of freshly squeezed juices; therefore, an understanding juice. Hand extraction is always the mildest extraction condition
of the changes in volatile compounds due to processing, and will usually contain the least amount of peel oil. However,
packaging, and storage can lead to commercial juices with better it has been demonstrated that even hand extraction can introduce
flavor quality. This study summarizes and evaluates our current small amounts of peel oil components into the juice (25, 26).
knowledge of aroma active volatile changes during commercial Mechanically squeezed orange juice contains higher concentra-
processing and storage, and odor changes due to packaging tion levels of certain aldehydes (octanal, nonanal, and decanal)
interactions as well as off-odors produced during storage via and terpenes (mainly, limonene, myrcene, and linalool) than
chemical or microbial means. A compilation of odor-active fresh hand-extracted juices, as they are also present in the peel
compounds in processed orange juice gathered from GC- oil (27, 28). Consequently, mechanically squeezed orange juices
olfactometry studies is also presented. To our knowledge, this will have a sensory profile somewhat different from that of
is the first comprehensive review of processed orange juice comparable hand squeezed juices.
flavor. Juice Finishing/Pulp Content. Immediately after extraction,
commercially produced juices pass through a stainless steel
ORANGE JUICE AROMA screen to separate extraneous cell and segment wall material,
and embryonic seeds from the juice. In this process, a screw
Flavor volatiles in fruits and vegetables are secondary press is employed to separate as much juice as possible from
metabolites formed during normal ripening and maturation the unwanted solid material. The industrial term for this process
largely from fatty or amino acid precursors (8-10). As in many is called finishing, and the pressure used to separate juice from
fruits, the aroma of freshly squeezed orange juice is primarily this pulp is referred to as finisher pressure. Juice composition
attributed to aldehydes (e.g., acetaldehyde, hexanal, octanal, can be altered depending on the finisher pressure employed.
decanal, neral, geranial, and Z-hex-3-enal) and esters (e.g., Ethyl
High finishing pressures effectively squeeze the pulp so hard
butanoate and ethyl-2-methylpropanoate), in addition to smaller
that the liquid portion of the pulp is added to the juice. Those
numbers of alcohols (e.g., linalool), ketones (1-octen-3-one),
solid particles that pass through the finisher screen are subse-
and hydrocarbon terpenes (myrcene, R-pinene, and possibly
quently dispersed into smaller particles using homogenizers. At
limonene) (1, 11-18). All these odor-active compounds impart
a latter stage, some juice manufacturers add juice sacs to produce
citrus, green, sweet fruit, and floral odor notes to fresh hand-
a pulpy juice product as the physical appearance and mouth
extracted juice aroma (19-21). Fresh from the tree, hand
feel is what some consumers consider close to what they might
squeezed orange juice is the sensory standard for what orange
prepare at home.
juice should taste like. However, few people can enjoy juice in
this manner as citrus can only be grown in certain regions of The finely suspended solids, which give juice its turbid
the world. An ideal processed orange juice would maintain all appearance, are referred to as cloud. These suspended solids
the sensory perceptions of the freshly squeezed juice. However, retain many juice volatiles. Juice volatiles partition between the
certain chemical laws dictate that when juices are subject to insoluble pulp/cloud and aqueous serum. Hydrocarbons (mono
thermal processing and postproduction packaging/storage condi- and sesquiterpene) are almost exclusively (80-90%) associated
tions, specific components will undergo reactions that will alter with pulp, whereas oxygenated compounds (esters, alcohols, and
the sensory profile. Several of the original sensory descriptors aliphatic aldehydes) are more closely associated with the
will be lost or diminished, and new sensory attributes will serum (2, 29-31). If the juice is clarified to remove this finely
eventually appear. As a result, there have been extensive suspended material, an enormous amount of aroma compounds
searches for alternate processing techniques, which would are eliminated (32), and the flavor of the clarified juice is altered.
maintain more of the fresh juice aroma attributes (22, 23). As It has been reported that the volatile compounds associated with
it currently stands, the aroma of orange juice is profoundly suspended solids (pulp and cloud) from a freshly squeezed
affected by processing, packaging, and storage conditions. The orange juice represent ∼80% of total juice volatiles (29).
aroma changes are largely determined by the time-temperature Because pulp content and particle size can be controlled under
conditions used to stabilize the juice, whether the juice is commercial production conditions, commercially produced
evaporated, the type of container, and storage conditions as well orange juices will have a different pulp content and physical
as the skill and care of the manufacturer. distribution than hand squeezed juices (33).
Juice Extraction. Botanically, oranges (Citrus sinensis) are Deaeration/Centrifugation. Deaeration is the process of
berries with an aromatic peel and a fleshy interior. The peel removing/reducing entrained air from the juice, just prior to
consists of an orange colored outer layer called the flavedo, thermal treatment, and can affect juice quality (34-37).
which contains oil glands and pigments, and a white spongy Entrained air can cause foaming related fill problems during
inner layer called the albedo. The fleshy interior or endocarp the packaging step as well as accelerate vitamin C degradation
consists of wedge shaped sections (segments) filled with during storage. Deaeration is employed only for those juices
numerous fluid-filled sacs or vesicles. These juice sacs constitute that will not undergo concentration as the concentration process
the edible portion of a citrus fruit and provide the primary source removes entrained air along with water and most aroma volatiles.
of the citrus juice (24). The juice is liberated when the juice For single strength (nonconcentrated) juices, deaeration is
vesicles are ruptured during physical extraction. This complex typically accomplished by exposing the juice to a partial
Review J. Agric. Food Chem., Vol. 56, No. 21, 2008 9787

vacuum, although other processes such as centrifugation are these odor defects in irradiated orange juice were sulfur
available. Deaeration can significantly reduce the most volatile compounds such as dimethyl sulfide (cabbage-like odor),
alcohols, aldehydes, and terpene hydrocarbon concentrations if dimethyl disulfide (onion-like, cabbage-like odor), methanethiol
not carefully controlled. Juice flavor quality will be diminished (cabbage-like), and dimethyl trisulfide (cabbage-like odor).
as many of these volatiles are important contributors to orange Concentrated, Reconstituted, and Not from Concentrate
juice aroma. Even though ester and ketone concentrations were Juices. Most orange juices are mechanically extracted and
essentially unaffected by the deaeration process, one study (34) concentrated to reduce the cost of transportation and storage
concluded that the major changes in orange juice volatiles were (46). It is simply more economical to ship a concentrated juice
due to deaeration and not to pasteurization. and add water at the destination rather than shipping juice with
Thermal Processing. Heating is employed to destroy spoilage all its natural water content. The commercial processes of
microorganisms as well as inactivate enzymes that destabilize concentrating orange juice usually involves the removal of water
the juice cloud and diminish juice quality during storage (38). at high temperature with slight vacuum for short times followed
Even though high temperature-short time procedures are by recovery and concentration of volatile aromas and their
employed, juice aroma is altered due to losses of original aroma addition back to the concentrated product (47). However, it has
impact volatiles (mainly aldehydes and esters) and the formation been noted that some juice manufacturers do not restore all the
of new volatiles or their precursors. When orange juice is heated, original volatiles, probably for economic reasons (48).
a complex series of chemical reactions are initiated involving The concentrated juice can be frozen and sold as frozen
peel oil components, phenolic compounds, sugars, amino acids, concentrated orange juice, FCOJ, or stored and shipped in bulk
lipids, ascorbic acid, and sulfur-containing components (39). to a distant distribution point where dilution, reheating, and
Many of the products of these reactions include oxygen-, sulfur-, packaging occurs. These juices are designated as reconstituted
and nitrogen-containing compounds. Many of the most potent from concentrate, RFC. The aroma of many RFC juices are said
oxygen-containing aroma volatiles (aldehydes, ketones and to be heated or processed, differing from that of freshly squeezed
alcohols) are produced from the peroxidation of unsaturated fatty oranges (19, 21, 48) This off-odor is observed most commonly
acids. Heating increases the rate at which a range of alcohols in canned RFC juices, which have been heated twice, one during
such as R-terpineol are produced from acid-catalyzed hydration the concentration process and again after the juice has been
of terpenes, the degradation of cinnamic acids, giving rise to diluted with local water and hot filled to sterilize the can and
aromatic aldehydes and alcohols, the degradation of carbohy- lid. These thermal treatments (high temperature/times) induce
drates forming furanaldehydes, furanones, and other Maillard- chemical changes in orange juices, which severely degrade the
type compounds, and the degradation of free amino acids original fresh orange juice volatiles and produce new volatiles.
yielding Strecker aldehydes. Although sulfur-containing com- It has been demonstrated that to generate this type of off-flavor
pounds can be formed in natural products as a result of under laboratory conditions (glass containers), orange juice must
biochemical and enzymatic pathways, many important sulfur be heated to 96 °C for 6 s (49). Commercially, juices are heated
aroma compounds are produced during the thermal processing in contact with stainless steel surfaces.
of food. The primary source of sulfur, from which sulfur- As the demand for higher quality orange juice has increased,
containing aroma compounds may be derived, are the sulfur studies have been undertaken to identify flavor changes produced
amino acids, cysteine, cystine and methionine (40). in the preparation of various juice types and how to avoid or
As conventional pasteurization treatment can negatively affect minimize them (3, 42, 44, 50, 51). Selected volatiles from
the flavor of orange juice, different heating processes have been pasteurized, not from concentrate, NFC, orange juices were not
tested on orange juices. Leizerson and Shimoni (41) examined markedly different from those of fresh juice, whereas RFC juices
the influence of ohmic heating on the quality and shelf life of had reduced levels of acetaldehyde, methyl acetate, ethyl acetate,
orange juice compared to that of conventionally pasteurized and ethyl butanoate, and slightly elevated levels of decanal,
orange juice. They concluded that ohmic-heated orange juice octanal, and linalool (52). RFC orange juices were found to
had higher aroma volatile concentrations than conventional contain less of the highly volatile aroma compounds, which are
pasteurization. The lower initial heat load during pulsed electric thought to give juice a fresh, fruity note (53-55). A recent study
fields treatment might induce fewer chemical reactions, resulting reported marked differences in volatile levels between different
in greater retention of initial flavor compounds. In addition, orange juice types (54). Freshly extracted and commercial
sensory experiments indicated that although assessors could unpasteurized juices contained greater amounts of the more
distinguish between fresh and pasteurized samples and between volatile aroma compounds than RFC (twice heated) juices. For
pasteurized and ohmic-heated juices, they could not differentiate example, fresh unpasteurized juice contained 11 to 53 times
between fresh and ohmic-heated orange juice. Thus, ohmic more acetaldehyde than the RFC juices. The unheated juices
heating produced a juice that retained most of the sensory also contained a greater number of volatiles. In unheated juices,
attributes of the initial juice and still reduced microbial and 11-12 esters, 13 aldehydes, and 25-27 terpenes were identified,
enzymatic activity to required levels. Min and co-workers (42) whereas RFC juices contained only 4-6 esters, 7-8 aldehydes,
obtained similar results in their study of microbial, nutritional, and 18-20 terpenes, suggesting that the restoration of juice
flavor, and sensory properties of orange juice exposed to volatiles in the RFC juices was incomplete. Total terpene and
commercial-scale pulsed electric field processing. Baxter and alcohol peak areas were similar in all samples, but total aldehyde
co-workers (43) subjected Navel orange juice to high pressure and ester concentrations were significantly higher in the
processing. GC-MS analysis demonstrated that the levels of 20 unheated juices. Unfortunately, sugar/acid levels were not
key aroma compounds in conventional temperature treatment reported; therefore, the influence of fruit maturity on juice
and high pressure juice were similar. Pasteurization of orange volatiles could not be evaluated. In another study, which
juice using gamma irradiation has also been examined (44, 45). developed from a sensory survey of orange juices, some canned
However, the elevated doses necessary for controlling micro- RFC juices were not perceived as orange juice. These juices
organisms, lead to the formation of off-odors that rendered the were described by a trained panel as tropical fruit/grapefruit,
product unacceptable. Some of the compounds responsible for heated/caramel, and moldy, whereas fresh hand-squeezed orange
9788 J. Agric. Food Chem., Vol. 56, No. 21, 2008 Review

juices completely lacked these sensory descriptors (48). The demonstrated that this compound is rarely aroma active in
volatiles from these atypical orange juices were further examined commercial orange juices, suggesting that the added R-terpineol
using GC-O, GC-MS, and GC-PFPD using SPME. The off- may have contained aroma active impurities. The odor threshold
flavor RFC juice contained 1 ester, 7 aldehydes, 12 terpenes, 8 for R-terpineol in orange juice is very high, 16.6 mg/L (68),
sulfur compounds, 2 furanones, 2 phenols, and other minor and rarely exceeded in commercial orange juices.
aroma-active compounds. The atypical aroma was attributed to Storage Temperature. There is a general agreement in the
the strong contribution of sulfur volatiles. Four of the 12 most literature that storage temperature is the major factor limiting
intense aroma peaks were sulfur compounds that included shelf life in juices (3, 4, 69-71). The overall aroma of orange
methanethiol, 1-p-menthene-8-thiol, 2-methyl-3-furanthiol, and juices does not change significantly if they are stored at
dimethyl trisulfide. refrigerated (4-6 °C) temperatures for up to 16 weeks, but
changes in aroma compounds have been observed in orange
ODOR CHANGES DUE TO PACKAGING AND STORAGE juices stored at higher storage temperatures. A gradual decrease
in several flavor components (ethyl butanoate, hexanal, octanal,
Orange juice is packaged either as hot juice to sterilize the neral, and geranial) combined with an increase in undesirable
container and lid or as a chilled juice under aseptic conditions compounds (ethyl acetate, R-terpineol, and furfural) in asepti-
into a sterilized container and lid. The former process reduces cally package orange juice was observed during 8 months of
many of the original aroma volatiles and induces off-flavor storage at 21 and 26 °C (72). A linear increase in R-terpineol
formation as the extended time at elevated temperatures with increasing storage time due to limonene degradation in a
promotes flavor degrading reactions. Volatile changes during nonoxidative pathway was observed (69). In another storage
orange juice storage have been the subject of research for over study comparing concentration differences due to storage
40 years, even though the storage containers have changed from temperature, commercial juices stored for 12 weeks at -18 °C
tin-coated steel cans and glass bottles to multilayer gable top contained approximately 1 ppm of R-terpineol, whereas the same
and PET (polyethylene terephthalate) blow molded containers. canned juices stored at 35 °C for the same time period reached
Changes in aroma compounds during storage are due to storage concentrations ranging from 3.4 to 5.5 µg/mL (62). Since
time and temperature, oxygen content, light exposure, and
R-terpineol is formed more rapidly from linalool than limonene,
container sorption or chemical contamination. Of all these
the linalool/R-terpineol ratio has been suggested as a means of
factors, storage temperature is the most important (3). Early
evaluating orange juice storage time/conditions (73).
orange juice storage studies concentrated on readily observable
Packaging Interactions. Several studies have shown that
and/or easily measured changes such as juice darkening (non
considerable amounts of aroma compounds can be absorbed by
enzymatic browning) and loss of ascorbic acid due to oxygen.
the food-packaging materials (4, 5, 72). Some taints could
Ascorbic acid loss was tracked during several storage studies
migrate from the packaging material into the juice (74). In a
and was directly related to oxygen content (3, 56, 57), but was
recent flavor absorption study involving low-density polyeth-
not directly responsible for flavor changes. Increases in terpene
ylene (LDPE), polycarbonate (PC), and polyethylene tereph-
alcohols were observed and attributed to acid-catalyzed hydra-
thalate (PET) in contact with orange juice, it has been shown
tions (58). Later studies focused on furfural as an indicator of
increased storage abuse (57, 59, 60). Although furfural can be that no sensory significant differences were found between
an indicator of juice that has experienced elevated temperatures polymer-treated samples and controls (4). Thus, in spite of the
(as an early Maillard reaction product), its aroma threshold is fact there are losses of flavor volatiles, they do not influence
rarely exceeded. orange juice flavor perception significantly after 29 days of dark
Storage Off-Flavors. Off-flavors are a major factor in storage at 20 °C. This may be due to the fact that the major
consumer acceptance, and those specific for citrus have been components sorbed by the packaging material were terpenes
reviewed (38, 61). In a study of off-flavors produced in canned with little odor activities. This finding agrees with a similar
orange juice stored at 35 °C for 12 weeks, three compounds GC-O study by Marin and co-workers, who concluded that the
(R-terpineol, 4-vinylguaiacol, and Furaneol) were found at plastic polymers LDPE and Surlyn did not significantly alter
elevated levels (62). Both 4-vinylguaiacol and Furaneol were the odor-active volatiles in orange juice, even though a
reported in orange juice for the first time. When these three significant decrease in limonene was observed (75). Several
components were added to fresh juice, they produced the charac- volatiles, including ethyl acetate, were found to increase in an
teristic odor of aged or heat-abused juice. Today, we recognize aseptically packaged fruity soft drink during storage (74). This
that R-terpineol and Furaneol exist at low levels in pasteurized juice. increase was due to the migration of solvent from laminated
It is also worth noting that the taste panel observed an increased containers, and it varied widely between individual packages. Most
grapefruit character in these juices that was not associated with packaging studies examined oxygen barrier properties of various
nootkatone. This grapefruit character has recently been shown materials under various storage conditions (3, 76, 77), whose effect
to be due to thermally induced sulfur volatiles (48). Of the three will be discussed in the next section. Storage temperature was more
storage off-flavors, 4-vinylguaiacol was the most potent, and it important than oxygen barrier properties.
has been extensively studied (63-66). Elevated and accelerated Oxygen Effects. Although considerable efforts are made to
temperature storage studies have shown that this compound has minimize oxygen content in the production of citrus juices, there
a relatively high energy of activation requirement and its is little evidence that the amount of oxygen directly alters the
presence as an aroma active compound indicates that the juice aroma of citrus juices during storage. In a five month (22 °C)
has been thermally abused. 4-Vinylguaiacol concentrations single strength juice storage study with dissolved oxygen levels
remain essentially unchanged and never exceed its aroma of 0.6, 1.8, 6.5, and 10.1 ppm stored, oxygen removal did not
threshold when stored at 4 °C for up to 16 weeks, but when improve product shelf life based on sensory evaluations (56).
stored at 40 °C, its concentration increases rapidly and exceeds However, it is quite likely that under these conditions other
its aroma threshold after only 6 weeks (65). R-Terpineol was flavor degrading reactions may have masked any effect due to
reported to produce a stale, musty, or piney off-flavor when oxygen. A later study (78) examined the effect of enzymatic
added to orange juice (62); however, GCO studies (1, 67) have deoxygenation, using glucose oxidase-catalase immediately after
Review J. Agric. Food Chem., Vol. 56, No. 21, 2008 9789

juice extraction but found no improvement in the shelf life of Table 1. Aroma Active Hydrocarbon Terpenes in Processed Orange Juice
pasteurized juices due to oxygen reduction. The primary effect
of oxygen is to oxidize ascorbic acid producing dehydroascorbic
acid (79), which contains an R-dicarbonyl group and can take
part in the production of Strecker aldehydes from the corre-
sponding amino acids. The production of methional from
methionine is probably due to this process.
Light Effects. The combination of light and oxygen are
necessary factors in lipid peroxidation, producing a number of
potent aldehydes (80). Both factors have been examined as
factors in flavor changes observed during orange juice
storage (81-83) but not attributed to lipid peroxidation. When
orange juice is exposed to light in the presence of oxygen, an
oxidized or cooked off-flavor was observed (81). Off-flavors
were not observed if the samples were exposed to light but
oxygen was excluded (83). Interestingly, it had been demon-
strated in lipid storage studies that free fatty acids increased
3-fold during a 16 month storage study at 4 °C and 8-fold at
29.4 °C (84). It has yet to be established that the orange juice
off-flavors observed in the presence of light and oxygen were
due to lipid peroxidation.

ODOR CHANGES DUE TO MICROBIAL CONTAMINATION

perception is limited because of high odor thresholds. Limonene,
Microorganisms (molds, yeasts, and bacteria) can cause myrcene, R-pinene, and p-cymene are the four terpene hydro-
spoilage and sensory defects in fruit juices. Lactic acid bacteria carbons commonly reported in processed orange juices (Table
are found most frequently in fruit juices, and orange juice 1). Limonene is the most abundant terpene hydrocarbon in
spoilage is usually characterized by a vinegar or butter-milk orange juice, and its concentration in processed orange juice is
odor (85). The metabolic products of this biological contamina- much higher than in fresh hand squeezed juices. This variability
tion include diacetyl (butane-2,3-dione), acetoin (3-hydroxy-2- arises because most of the limonene comes from peel oil and is
butanone), and odor active acids (e.g., acetic acid and butyric introduced into the juice during mechanical extraction. In spite
acid). Recently, different strains of Alicyclobacillus have been of its high concentration, limonene is not a key flavor impact
associated with medicinal or antiseptic off-flavors in orange juice compound in orange juice. Nevertheless, limonene is a necessary
(7). The medicinal off-flavors associated with Alicyclobacillus component of any orange juice odor model, although its exact
species have been attributed to metabolite products of these function is still uncertain (99). Moreover, many reports have
bacteria and have been identified as guaiacol (2-methoxyphenol) mentioned that the high concentration of this terpene is
(86) along with two halogenated compounds (2,6-dichlorophenol associated with off-odors (39, 73) or a negative sensory mouth
and 2,6-dibromophenol) (87). The two halogenated phenolic feel commonly referred to as peel burn. Thus, limonene, because
compounds are not produced by all species and strains of of its unsaturated sites, can also thermally induce products such
Alicyclobacillus (7), but guaiacol is always the primary meta- as carvone via an oxidative pathway (100), which can degrade
bolic product.
the flavor quality of the juice. Myrcene is the next most abundant
terpene. It has a green, mossy odor and is a much stronger
ODOR-ACTIVE VOLATILES IN PROCESSED ORANGE odorant than limonene, even though limonene is present in
JUICES considerably higher concentrations. R-Pinene with a pine-tree,
resin aroma can make a positive background contribution to
Early orange juice studies focused on identifying and
quantifying volatiles found at the highest concentrations orange aroma, although its level in orange juice directly depends
(51, 52, 88-92). At the time of these studies, it was thought on the peel oil content of the juice.
that those volatiles found at the highest concentration should Oxygen-Containing Volatiles. Oxygenated aroma com-
contribute the most to flavor. Even before the advent of gas pounds make a major contribution to the aroma of numerous
chromatography-olfactometry, it had been shown that minor foods. In fruits and vegetables, they can be formed from
components make major contributions to flavor (93), and unsaturated terpenes, fatty acids, sugars, or amino acid
since then, it has been estimated that less that 5% of all food precursors.
volatiles possess aroma activity (94). Gas-chromatography- Aldehydes. Aldehydes are secondary metabolites formed
olfactometry (GC-O) has been shown to be a powerful during normal ripening and maturation of orange fruits. They
technique to characterize and tentatively identify odor-active are important in terms of orange odor quality and their
compounds, which are typically confirmed by MS whenever concentrations increase with fruit maturity (91). Some aldehydes
possible. Recent orange juice studies (67, 75, 95-98) have impart a pleasant green and citrus note to fresh squeezed orange
employed GC-O to determine which volatiles are responsible juices, whereas others impart fatty, metallic notes. Before
for the sensory changes in orange odor due to thermal individual aldehydes could be quantified, chemical tests for total
processing and storage and are described in the following aldehydes were used as a rough measure of flavor quality of
sections. citrus oils (101, 102). Some reactive aldehydes such as
Hydrocarbon Terpenes. Hydrocarbon terpenes are the acetaldehyde, (Z)-hex-3-enal, neral, and geranial are present at
predominant chemical class within orange volatiles and comprise super threshold levels in fresh squeezed juice but at diminished
over 95% of the peel oil. However, their contribution to odor levels in processed orange juices if at all. Much of the perceived
9790 J. Agric. Food Chem., Vol. 56, No. 21, 2008 Review

flavor quality of orange juice is produced by the relative amounts Linalool is the most aroma intensive alcohol and possesses a
of these aldehydes. distinctive floral, sweet odor. Although linalool is also present
Twelve aroma-active aldehydes have been identified in in fresh hand squeezed juices, its concentration level is higher
processed orange juices (Table 2). Neral and geranial in processed oranges juices as most of it originates from the
(formerly called citral) are important volatile components of peel oil (26). Highest levels of linalool are observed in RFC
orange juice and peel oil. These two isomeric monoterpene juices as a result of flavor restoration efforts. Excessively high
aldehydes are typically found in the ratio of 2:3 and possess levels of linalool and/or others terpenes can produce flavor
a lemon, citrus-like odor. They are highly unstable, and their imbalances.
concentrations are diminished during thermal processing and Under orange juice acidic conditions (pH ∼3.8), hydrocarbon
storage. R-Sinensal and β-sinensal are two isomeric forms terpenes undergo a series of oxidative hydration-dehydratation
found as a 2:1 ratio of β-sinensal to R-sinensal and are reactions that produce alcohols (e.g., terpinen-4-ol, R- terpineol,
described with a sweet aroma. and β-terpineol) and other products (e.g., p-cymene or
Long-chained unsaturated fatty acids are important precur- terpinolene) (38, 61). The formation of these thermally induced
sors of many volatile off-odors compounds, such as alk-2,4- terpene alcohols can alter the overall sensory properties of
dienals, alk-2,6-dienals, and aliphatic saturated aldehydes orange juice. Linalool degrades primarily to R-terpineol but also
(e.g., hexanal, octanal, and decanal). It has been shown that to 1,8-cineole, geraniol, nerol, and terpinen-4-ol (26, 73, 105).
concentrations of all of these aldehydes increase when orange Although both limonene and linalool can undergo acid-catalyzed
juice is heated (1, 14, 97). Concentrations of several straight- hydrations to form R-terpineol and juices contain much less
chain aldehydes such as octanal, nonanal, and decanal are linalool relative to limonene, linalool is more reactive and
found at higher levels in processed juices because they are produces most of the formed R-terpineol. Although Tatum and
constituents of the co-mingled peel oil introduced during juice co-workers reported that orange juices spiked with 2.5 ppm of
extraction (103). Most of the alk-2,4-dienals and alk-2,6- R-terpineol imparted a stale, musty, or piney note into the juice
dienals possess a fatty, metallic, or fried odor that could (62), GCO studies have shown that R-terpineol is rarely aroma
contribute to off-flavors when out of balance with the more active. R-Terpineol is generally considered a marker for heat-
desirable aldehydes. As seen in Table 2, there are nine abused orange juices (66, 105) rather than something that
aliphatic aldehydes, which have been identified in processed directly impacts juice flavor. Bazemore and co-workers reported
juices using GC-Olfactometry. that the odor of terpinen-4-ol, described as metallic/stale, was
Some important aldehydes are restored in reconstituted from judged stronger in the heat-abused juice than in the lightly heated
concentrate, RFC, juices by the addition of aqueous essence juice. A recent study of the off-odors in canned RFC orange
and peel oil after the original volatiles were lost during the juices observed elevated levels of p-cymene, 1,8-cineole,
concentration process. However, because of the relatively low geraniol, nerol, terpinen-4-ol, and 4-vinylguaiacol (48).
economic value of this product, it is rare that all of the aroma- Ketones and Acids. One of the most intense odor-active
active aldehydes are restored. The incomplete or inadequate aliphatic ketones in orange juice is 1-octen-3-one. It is a lipid
restoration of these volatiles contributes to the lower flavor decomposition product, and its odor has been described as
quality perception of these juices compared to that of fresh metallic and mushroom-like. It is extremely potent with an odor
squeezed or not from concentrate, NFC, juices. threshold in water of 0.005 µg/L (10). Two ketone noriso-
Esters. Esters also make an important contribution to prenoids, β-ionone and β-damascenone, are also odor-active
orange odor, and the level of total esters in aqueous essence compounds in processed orange juices and possess a floral note
has been used as a quality index (16). However, when fruits at their juice concentrations. Nevertheless, they have only been
are homogenized such as in the processing of juice, many reported by a single research group (48). β-Ionone has been
esters are rapidly hydrolyzed by hydrolase enzymes, thus reported as among the more odor-active volatiles in freshly
reducing their concentrations. Also, their concentrations are squeezed Valencia orange juices (11). Its odor is described as
dramatically reduced after thermal processing. Thus, only 4 sweet floral and raspberry in orange juice and has an extremely
esters have been reported in processed juices using GC-O lowodorthresholdinbothwaterandorangejuicepump-out(68,106).
(Table 2). Ethyl butanoate is one of the most potent odorant β-Damascenone is described as tobacco, apple, and floral and
of processed juices, and it is an important contributor to contributed to 19% of the floral compounds in freshly squeezed
desirable flavor in orange products (67, 97). Lower levels of orange juice analyzed by GC-O (13). According to these authors,
ethyl butanoate, as well as total esters, have been observed its concentration ranged from 0.122 to 0.281 µg/L in orange
in processed juices (52) compared to the initial juice. Esters juice not from concentrate and as high as 0.145 to 0.690 µg/L
are responsible for the fruity top-notes present in fresh juice in reconstituted orange juice from concentrate (107). This
that are often missing or diminished in thermally processed norisoprenoid can be produced from neoxanthin (108).
orange juice products. Carvone is an off-flavor ketone produced from the oxidation
Wine lactone (3a,4,5,7a-tetrahydro-3,6-dimethyl-2(3H)-ben- of limonene and can be found in two enantiomeric forms: S-(+)-
zofuranone) is a cyclic ester (lactone), which has one of the carvone, which smells like caraway, and its mirror image, R-(-)-
highest flavor dilution (FD) factors in processed orange juice carvone, which smells like spearmint. It is thought to degrade
(67). It may be speculated that wine lactone is formed from orange juice quality, and its concentration is expected to increase
linalool via a hydrolytic conversion (104). However, it should as a result of thermal treatment and oxidative storage (1, 48, 67).
be noted that wine lactone has never been reported as aroma In previous orange juice studies, carvone odor was described
active in any orange juice head space study. It has only been both as a caraway-like odor quality (67) and also as a minty
observed in solvent-extracted samples, suggesting that this potent odor (48).
compound (along with vanillin) has a very low vapor pressure A few acids have been identified as odor-active compounds
at room temperature and at 37 °C. in processed juice, although their contribution to the overall juice
Alcohols. Five terpene alcohols with odor activity have been odor is minimal (48, 67, 95). They are thought to be formed by
reported in processed orange juices using GC-O (Table 2). fatty acid oxidation or by microbiological spoilage.
Review J. Agric. Food Chem., Vol. 56, No. 21, 2008 9791

Table 2. Oxygen Containing Compounds in Processed Orange Juice

9792 J. Agric. Food Chem., Vol. 56, No. 21, 2008 Review

Phenols. As seen in Table 2, five odor-active phenols have Table 3. Sulfur Containing Volatiles Found in Processed Orange Juice
been reported in processed orange juices, which individually
and collectively reduce flavor quality. The potent off-odor,
4-vinylguaiacol, is perhaps the most important. It is produced
from an odorless precursor, ferulic acid, which is capable of
producing both vanillin and 4-vinylguaiacol. Most ferulic acid
in orange juice is found in bound forms such as glycosides,
esters, and amides. However, acidity, thermal processing, and
subsequent high-temperature storage provide ideal conditions
for the release of ferulic acid from its bound forms (63, 109).
Ferulic acid can also be converted to 4-vinylguaiacol by yeast,
which has been found in concentrated orange juice (110).
The evidence for the formation of 4-vinylguaiacol from
ferulic acid has been demonstrated in a model juice system.
In terms of relative amounts, the majority of ferulic and other
cinnamic acids are found in the peel. Increased mechanical
pressure during fruit extraction will increase juice yield but
may affect product flavor due to the introduction of peel
components into the juice. Many of these peel-derived
phenolics are off-odor precursors. and/or biochemical pathways, many important sulfur compounds
Vanillin is an odor-active phenolic found routinely in solvent- are also thermally generated (114).
extracted fresh orange juice samples but is not one of the most Volatile sulfur compounds are also important as potential
potent odorants. At low concentrations, it might positively off-flavors in heated citrus products. However, there have
contribute to overall juice aroma, but its concentration is been few reports primarily because of the difficulty in
significantly higher in thermally processed juice (67) because measuring them. Earlier studies reported finding traces of
of the thermal degradation of ferulic acid and at that point is sulfur volatiles such as hydrogen sulfide, methanethiol,
typically a flavor defect. dimethyl sulfide, dimethyl disulfide, sulfur dioxide, and
Three additional aroma active phenols have been reported in carbonyl sulfide in the headspace of different citrus
processed orange juices: guaiacol, 2,6-dichlorophenol, and 2,6- juices (58, 115-117). Recent works have reported finding
dibromophenol. These compounds are responsible for the 3-(methylthio)-propanal (methional), 2-methyl-3-furanthiol,
medicinal or antiseptic off-flavors in thermally processed orange and 1-p-menthene-8-thiol in both fresh (13, 14, 96) and
juices contaminated by different species and strains of Alicy- processed orange juices (67, 96) as odor-active compounds
clobacillus (7) and have been previously discussed. (Table 3). Moreover, eight sulfur volatiles with odor activity
Furans and Furanones. Thermal degradation of sugars, (methanethiol, dimethyl sulfide, 3-mecapto-2-butanone, 2-meth-
amino acids, and ascorbic acid can produce off-flavors and yl-3-furanthiol, methional, 4-mercapto-4-methyl-2-pentanone,
nonenzymic browning products (111). These heat-induced dimethyl trisulfide, and 1-p-menthene-8-thiol) have been
degradations produce acids (acetic or butyric acid), furans (e.g., identified as off-odors in RFC canned orange juices (48).
furfural and 5-methyl furfural), furanones (e.g., 2,5-dimethyl- As canned RFC juices are heated twice, it is possible that
4-hydroxy-3(2H)-furanone and 2-ethyl-4-hydroxy-5-methyl- the majority of sulfur compounds identified were derived
from thermal processes and increased by ambient temperature
3(2H)-furanone), ketones, cyclopentanones, pyranones, and
storage. The prominent tropical fruit/grapefruit-like sensory
pyrroles (38, 62, 112). Some of them impart sweet, caramel-
attribute that these juices exhibited were correlated with such
like, or burnt sugar-like sensory impressions. However, other
major grapefruit juice aroma impact compounds such as 1-p-
reaction products such as furfural and 5-methylfurfural, whose
menthene-8-thiol and 4-mercapto-4-methyl-2-pentanone. El-
concentration increases due to thermal processing (95), are rarely
evated levels of 1-p-menthene-8-thiol were also observed in
aroma active as they have high odor thresholds. Because furfural
grapefruit juices that had been heated (118). Furthermore,
is formed by oxidative degradation of ascorbic acid (39), it has Tatum and co-workers (62) reported a grapefruit-like aroma
been used as an indicator of thermal abuse. in canned orange juices that had been thermally abused,
Furanones are Maillard reaction products, which have also although they could not identify the aroma-active compound
been identified in heated orange juices (62). Furaneol and responsible for this odor. All these sulfur-containing aroma
homofuraneol have been identified as odor-active compounds compounds are primarily derived from thermally induced
in canned orange juices (48). They were potent odorants in these reactions involving sulfur-containing amino acids, such as
juices, inducing caramel odor qualities. The canned juices were methionine. Thus, methional can be formed from methionine
described with a cooked/caramel odor defect, and these two by Strecker degradation (96), whereas 2-methyl-3-furanthiol
Maillard products contributed to this overall quality degrading can be produced either in the Maillard reaction (119) or from
sensory impression in the juice. the degradation of thiamin (98). 3-Mercapto-2-butanone may
Sulfur and Nitrogen-Containing Volatiles. Sulfur com- be derived from the Maillard reaction as well (119), and
pounds are potent aroma volatiles in many foods. Although they methanethiol oxidizes easily to dimethyl disulfide, which can
are present at extremely low concentration levels, they are often disproportionate to dimethyl sulfide and dimethyl trisulfide
significant in terms of odor activity as they often have even (9). Sulfur volatiles tend to be flavor degrading volatiles when
lower odor thresholds. Because they are typically found at levels present above threshold levels.
close to or below the detection limits of many instruments, they Finally, a single nitrogen-containing compound, 2-isopropyl-
are difficult to measure and have often been overlooked (113, 114). 3-methoxy-pyrazine, has been identified in processed juice as
Although they can be formed in natural products by enzymatic an odor-active volatile (67). This pyrazine is a powerful odorant
Review J. Agric. Food Chem., Vol. 56, No. 21, 2008 9793

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