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Vol. 34, No. 03, pp. 659 – 669, July – September, 2017
dx.doi.org/10.1590/0104-6632.20170343s20150669
* To whom correspondence should be addressed
This is an extended version of the work presented at the
11th Brazilian Congress of Chemical Engineering on Undergraduate Scientic Mentorship, COBEQ-IC 2015
Campinas, SP, Brazil
FATTY ACIDS PROFILE OF CHIA OIL-LOADED
LIPID MICROPARTICLES
M. F. Souza1, C. R. L.Francisco1; J. L. Sanchez2, A. Guimarães-Inácio2,
P. Valderrama2, E. Bona2, A. A. C. Tanamati1, F. V. Leimann2 and O. H. Gonçalves2*
1Universidade Tecnológica Federal do Paraná, Departamento de Alimentos, Via Rosalina Maria dos Santos, 1233,
Caixa Postal 271, 87301-899 Campo Mourão, PR, Brasil. Phone/Fax: +55 (44) 3518-1400
2Universidade Tecnológica Federal do Paraná, Programa de Pós-Graduação em Tecnologia de Alimentos, Via Rosalina Maria dos Santos,
1233, Caixa Postal 271, 87301-899 Campo Mourão, PR, Brasil. Phone/Fax: +55 (44) 3518-1400
*E-mail: odinei@utfpr.edu.br
(Submitted: October 14, 2015; Revised: August 25, 2016; Accepted: September 6, 2016)
ABSTRACT - Encapsulation of polyunsaturated fatty acid (PUFA)is an alternative to increase its stability during
processing and storage. Chia (Salvia hispanica L.) oil is a reliable source of both omega-3 and omega-6 and its
encapsulation must be better evaluated as an eort to increase the number of foodstus containing PUFAs to consumers.
In this work chia oil was extracted and encapsulated in stearic acid microparticles by the hot homogenization technique.
UV-Vis spectroscopy coupled with Multivariate Curve Resolution with Alternating Least-Squares methodology
demonstrated that no oil degradation or tocopherol loss occurred during heating. After lyophilization, the fatty acids
prole of the oil-loaded microparticles was determined by gas chromatography and compared to in natura oil. Both
omega-3 and omega-6 were eectively encapsulated, keeping the same omega-3:omega-6 ratio presented in the in
natura oil. Calorimetric analysis conrmed that encapsulation improved the thermal stability of the chia oil.
Keywords: encapsulation, polyunsaturated fatty acid, solid lipid microparticles, Salvia hispanica, MCR-ALS.
INTRODUCTION
The increasing demand for functional foods has directed
the market towards oering omega3-enriched foodstu.
It is a modern lifestyle challenge to meet the required
amount of polyunsaturated fatty acids (PUFAs) in order to
minimize the risk of chronic disease (Garg et al., 2006).
Chia (Salvia hispanica L.) oil have high nutritional value
since most of its constituents are triglycerides with PUFA
acids present in larger proportions and omega-3 content
between 60 and 68% (Capitani et al., 2012). PUFAs are
known to help reduce triglycerides and cholesterol levels
and other benecial eects have been observed regarding
coronary heart disease, hypertension and inammatory
disorders(Borneo et al., 2007; Harris et al., 2008). Although
sh oil is a less expensive source of omega-3, its use in
food formulations has been questioned due to unpleasant
sensory properties even after encapsulation (Martínez et
al., 2012; Muchow et al., 2009; Rodea-González et al.,
2012).
PUFAs are susceptible to oxidation(Ixtaina et al.,
2011), which can lead to a decrease in nutritional and
sensory quality. Encapsulation techniques are a promising
approach in order to protect substances from harm and to
meet shelf-life requirements (Gökmen et al., 2011; Gouin,
2004). There are a number of encapsulation techniques to
encapsulate liquid lipids (TAMJIDI et al., 2013a) such as
spray drying (Carneiro et al., 2013; Jimenez et al., 2006;
Rodea-González et al., 2012), cyclodextrin complexation
(XU et al., 2013), complex coacervation (Tamujidi et al.,
2012) and ultrasonic atomization (Klaypradit; Huang,
Brazilian Journal
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Brazilian Journal of Chemical Engineering
M. F. Souza, C. R. L.Francisco, J. L. Sanchez, A. Guimarães-Inácio,
P. Valderrama, E. Bona, A. A. C. Tanamati, F. V. Leimann and O. H. Gonçalves
660
2008). Borneo et al. (2007) obtained cream-lled sandwich
cookies containing encapsulated omega-3, demonstrating
the possibility of producing shelf-stable foods with
high levels of omega-3. Gökmen et al. (2011) observed
a reduction in the thermal oxidation of omega-3 from
axseed oil after its encapsulation. Rodea-González et al.
(2012) produced microparticles containing chia oil by spray
drying using whey protein concentrate-polysaccharide
matrices.
Hot homogenization is also an interesting technique
due to the natural compatibility between PUFAs and
the solid lipid matrix (Lacatusu et al., 2013; Muchow et
al., 2009; Salminen et al., 2013). Encapsulation by hot
homogenization is also favored by the fact that the liquid
oil hinders the solid lipid crystallization, generating a
less ordered microstructure or even an amorphous phase
(Tamjidi et al., 2013b). Although no solvent is required,
relatively high temperatures are needed for the proper
mixing of encapsulant and the encapsulated compound.
For this reason, attention must be paid to the possibility
of thermal degradation when unsaturated lipids are to be
encapsulated. Oil degradation may be detected by UVVis
spectroscopy, but the complexity of the obtained spectra
requires further signal treatment. Multivariate Curve
Resolution (MCR) is a suitable chemometric technique
since it can identify mixed signals and recover the relative
concentration of the substances and their respective spectra
(Março et al., 2014).In the case of unsaturated fatty acids,
thermal degradation can be evaluated by the formation of
degradation products such as conjugated trienes and dienes
and hydrolysis products (Gonçalves et al., 2014).
Moreover, some key points are still to be investigated
in the encapsulation of chia oil by the hot homogenization
procedure. First, the encapsulation eciency of each
PUFA must be determined since it can be aected by the
interactions between them and the encapsulant. Second, the
possibility of thermal degradation must be checked since
the system must be heated during the particle production
step. The objective of this work was to extract the oil from
chia seeds and encapsulate it in stearic acid microparticles
by the hot homogenization technique. Multivariate Curve
Resolution (MCR) was applied to determine if damage to
the oil occurred due to heating. Encapsulation eciency
was determined for both omega-3 and omega-6 using gas
chromatography.
EXPERIMENTAL SECTION
Materials
Chia seeds were acquired from the local market. Stearic
acid (Sigma-Aldrich, 99.5%) and Tween 80 (Dinâmica,
97%) were used as encapsulant and surfactant, respectively.
Distilled water was used as continuous phase. Methanol
(Isofar, 99.8%), chloroform (Vetec, 99.5%), ammonium
chloride (Vetec, 99.5%) and sulphuric acid (Vetec, 95%)
were used in the transesterication reaction. KBr (Sigma-
Aldrich, spectrophotometric standard) was used in the
spectrophotometric analyses.
Chia oil extraction
Total moisture of the chia seeds was determined and
then adjusted to 80% by adding distilled water. Then, the
extraction was performed according to the methodology
described by Bligh and Dyer (1959). Briey, triturated
chia seeds (15g) were added to methanol (30 mL) and
chloroform (15 mL) under mild stirring. Then, 15 mL
distilled water was added and stirred for another 5
minutes. The resulting solution was ltered and 20 mL
more chloroform was added. After 5 minutes stirring, the
solution was ltered again. Solvent was removed under
vacuum (-400 mmHg e 35ºC) and the chia oil was stored at
10°C protected from light.
Quantication of the degradation products by MCR-
ALS
Quantication of the oil degradation products
was carried out to determine if chia oil was prone to
degrade at the temperature used in the encapsulation
procedure (75°C). A sample of in natura chia oil (before
encapsulation) was heated and aliquots were collected at
28, 30, 40, 50, 60, 70 e 75ºC. The sample was then kept at
75ºC and additional aliquots were collected after regular
time intervals for 120 minutes. UV-Visible spectra (Ocean
Optics, Red Tide USB650, 1 nm resolution) were obtained
and the formation of degradation products was evaluated
by Multivariate Curve Resolution Alternating Least-
Squares method (MCR-ALS) as described by Gonçalves et
al.(2014). Spectra recovered by MCR-ALS were attributed
to their respective compounds according to Valderrama et
al. (2011).
Microparticles production
Chia oil-loaded microparticles were obtained by the
hot homogenization technique(Gonzalez-Mira et al., 2010)
such as non-steroidal anti-inammatory drugs (NSAIDs.
Aqueous phase was prepared dissolving Tween 80 (0.300
g) in distilled water (25 g) and heating to 75°C under
gentle stirring. Separately, stearic acid (0.625g) was melted
at 75°C in a borosilicate double walled vessel. Chia oil
was then added to the molten lipid and mixed for 1 minute.
Then, the aqueous phase was added to the vessel and stirred
for 3 minutes, resulting in an oil-in-water macroemulsion.
Sonication (Fisher-Scientic – Ultrasonic Dismembrator
120 W, 1/8” tip) was carried out for 3 minutes in a pulse
regime (30 seconds on and 10 seconds o). The sonicated
mixture was cooled in an ice bath, resulting in the
Brazilian Journal of Chemical Engineering Vol. 34, No. 03, pp. 659 – 669, July – September, 2017
Fatty acids prole of chia oil-loaded lipid microparticles 661
formation of solid lipid particles dispersed in water. They
were freeze dried before analysis. The same procedure was
also carried out without the addition of chia oil to obtain
blank microparticles.
Transesterication and Gas Chromatography (GC)
Fatty acids quantication was performed by CG using
methyl tricosanoate (23:0, Sigma-Aldrich) as internal
standard according to Hartman and Lago methodology
(Milinsk et al., 2008).Fatty acid methyl esters (FAMEs)
were separated and identied using chromatograph
standards (Sigma-Aldrich, F.A.M.E. Mix C14-C22).
The equipment setup was as follows: gas chromatograph
(Shimadzu, GC-2010 Plus AF) equipped with Split/
Splitless capillary injector, ame ionization detector
(FID), ow and pressure automatic controllers and a
100% dimethylpolysiloxane capillary column (Rtx-1,
30m x 0.25mm x 0.25µm). Transesterications were
performed in triplicate. Equation 1 was used in the FAMEs
quantication(Joseph and Ackman, 1992).
23:0
23:0
x CT
x
s MEA
AM F
MA MF
=
where:
Mx= Fatty acid concentration in the sample (mg.g-1oil);
M23:0 = internal standard mass (mg);
Ms = sample mass (g);
AX = peak area for each fatty acid;
A23:0 = peak area of the internal standard;
FCT = theoretical correction factor;
FMEA = conversion factor.
Microparticles characterization
Fourier transform infrared spectroscopy (FTIR) was
used to qualitatively evaluate chia oil encapsulation.
Lyophilized samples or in natura oil were mixed with
dry KBr and spectra were acquired in a Shimadzu
spectrometer (IR Anity-1, 32 cumulative scans) from
4000 to 400 cm-1.This procedure was carried out in
triplicate. Images from the microparticles were taken using
an optical microscope (BIOVAL, L2000A) coupled to a
digital camera. Dierential Scanning Calorimetry (DSC,
Perkin Elmer 4000) was used to investigate the thermal
behavior of in natura chia oil, oil-loaded microcapsules
and blank microcapsules. In the rst set of experiments,
approximately 5 mg of samples were placed on open
aluminum lids and heated from 0°C to 440°C at 20°C/min
under air atmosphere (100 mL/min) in order to investigate
if encapsulation inuenced the thermal stability of the
chia oil. In a second set of experiments, approximately 5
mg of samples were placed on closed aluminum lids and
heated from 0°C to 250°C at 20°C/min under a nitrogen
atmosphere (10 mL/min) to determine the enthalpy of
fusion and melting temperature of the encapsulant.
To determine encapsulation eciency (EE%,
Equation 2), an aliquot of the microparticles dispersion
was ltered in Amicon lters (100 kDa, Millipore) using
an ultracentrifuge at 14,500 rpm for 15 min. The liquid
phase containing the non-encapsulated fatty acids ([FA]
non-encapsulated) was transesteried as described above.
Also, the total concentration of fatty acids ([FA]total,
encapsulated plus non-encapsulated) was determined for
the lyophilized microparticles.
( )
% 100
total non encapsulated
total
FA FA
EE FA
−
−
=
RESULTS AND DISCUSSION
Chia oil composition
Chia seeds presented 9.5% humidity, which is in
accordance with values found in the literature (Ixtaina et
al., 2011). Total lipid content was 19.80%, while values
from 20.30 to 33.60% were reported when hot hexane or
pressing were used for extraction (Ixtaina et al., 2011). It
is worth noting that Bligh-Dyer (Bligh and Dyer, 1959)
is a cold method thus minimizing lipid oxidation during
extraction.
Thermal degradation of in natura chia oil by MCR-
ALS
Figure1 presents the relative concentration of
tocopherol and degradation products (conjugated dienes/
trienes and hydrolysis products) for the in natura chia oil
(before its encapsulation) during heating to 75°C then
keeping at this temperature for 2 hours. In Figure 2, UV-
Vis spectra recovered by MCR-ALS of tocopherol and
degradation products are presented.
It is worth noting that the concern about thermal
degradation arises from the fact that the encapsulation
procedure demands heating to melt the lipid encapsulant,
which could damage the unsaturated fatty acids present
in chia oil. UV-Vis spectra detected the presence of
tocopherol (Ixtaina et al., 2011) and that its concentration
started decreasing only after approximately 2 hours at
75°C. Hydrolysis products were also formed after this
heating time. Gonçalves et al. (2014) have demonstrated
that temperature and oil composition are key factors for
tocopherol concentration decrease and oil degradation for
(1)
(2)
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M. F. Souza, C. R. L.Francisco, J. L. Sanchez, A. Guimarães-Inácio,
P. Valderrama, E. Bona, A. A. C. Tanamati, F. V. Leimann and O. H. Gonçalves
662
a number of dierent edible oils. During the encapsulation
procedure adopted in this work, oil is heated at 75°C for
only 7 minutes, meaning that one may not expect chia oil
degradation caused by the encapsulation conditions (time
and temperature).
Figure 1. Relative concentration proles of tocopherol (—) and conjugated dienes/trienes and hydrolysis products (- - - -) for in natura chia
oil (before encapsulation) (A) in dierent temperatures and (B) at 75°C for 2 hours.
Figure 2. UV-Vis spectra recovered by MCR-ALS of (- - - -) tocopherol and (——) conjugated dienes/trienes and hydrolysis products.
Fatty acids identication and quantication
Figure 3 presents the separation of the fatty acids methyl
esters of the in natura chia oil before its encapsulation,
while the concentration (mg.g-1) of each compound is
presented in Table 1.
The most concentrated fatty acids found were palmitic
(C16:0, 67.88 mg.g-1), oleic (C18:1n-9, 54.09 mg.g-
1), linoleic (LA, 18:2n-6, omega 6, 181.94 mg.g-1) and
alpha-linolenic (LNA, 18:3n-3, omega-3, 565.52 mg.g-1).
Linoleic and alpha-linolenic essential fatty acids (LA e
LNA) were identied at 12 and 14 minutes, respectively
and corresponded to 20.21% and 62.80% of the total lipid
in chia oil. These results are in accordance with those
presented by Capitani et al. (2012)and Martínez et al.
(2012).
Edible oils presenting a ΣPUFA:ΣSFA ratio above 0.45
and n-6:n-3 ratio from 1:1 to 2:1 are recognized as ideal to
human dietary intake (Wood et al., 2004), meaning that the
oil presented high nutritional quality.
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Fatty acids pro le of chia oil-loaded lipid microparticles 663
Figure 3. In natura chia oil chromatogram (before encapsulation).
Table 1. Fatty acids concentration in in natura chia oil (before encapsulation).
Fatty acid Concentration (mg.goil-1)
C14:0 (myristic acid) 0.32 ± 0.01
C16:0 (palmitic acid) 67.88 ± 1.75
C18:0 (stearic acid) 27.91 ± 0.73
C18:1 n-9 (oleic acid) 54.09 ± 1.36
C18:2 n-6 (linoleic acid) 181.94 ± 5.75
C18:3 n-3 (α linolenic acid) 565.52 ± 24.4
C20:0 (arachidic acid) 2.35 ± 0.04
C22:0 (behenic acid) 0.78 ± 0.03
Ratios and sums*
ΣSFA 99.24
ΣMUFA 54.09
ΣPUFA 747.46
ΣPUFA:ΣSFA 7.53
n-6:n-3 0.32
*ΣSFA = saturated fatty acids; ΣMIFA = monounsaturated fatty acids; ΣPIFA = polyunsaturated fatty acids.
Chia oil-loaded particles were lyophilized and the
powder was transesteri ed and compared to in natura oil
(Figure 4). Also, non-encapsulated oil was separated from
the particles by ltration and subjected to transesteri cation
(Figure 5). Encapsulation e ciency (EE%) of omega-3
and omega-6 are presented in Table 2.
Brazilian Journal of Chemical Engineering
M. F. Souza, C. R. L.Francisco, J. L. Sanchez, A. Guimarães-Inácio,
P. Valderrama, E. Bona, A. A. C. Tanamati, F. V. Leimann and O. H. Gonçalves
664
Figure 4. Chromatograms of in natura chia oil (red) and oil-loaded particle (black).
Figure 5. Chromatograms of non-encapsulated chia oil (red) and oil–loaded particles (black).
Brazilian Journal of Chemical Engineering Vol. 34, No. 03, pp. 659 – 669, July – September, 2017
Fatty acids prole of chia oil-loaded lipid microparticles 665
Table 2. Fatty acids concentration of the chia oil-loaded microcapsules and the non-encapsulated oil.
Concentration (mgFA/gparticles)
Fatty acid Oil-loaded microcapsules Non encapsulated oil
C14:0 (myristic acid) 13.24 ± 0.15 0.84 ± 0.15
C16:0 (palmitic acid) 165.07 ± 64.91 23.67 ± 1.96
C18:0 (stearic acid) 682.17 ± 213.04 24.35 ± 7.35
C18:1 n-9 (oleic acid) 90.67 ± 0.80 21.51 ± 5.09
C18:2 n-6 (linoleic acid) 124.01 ± 0.19 9.57 ± 2.37
C18:3 n-3 (α linolenic acid) 388.71 ± 17.04 18.11 ± 3.29
C20:0 (arachidic acid) 7.35 ± 0.28 -
C22:0 (behenic acid) 1.34 ± 0.72 -
Ratios and sums*
ΣSFA 869.17 48.86
ΣMUFA 90.67 21.51
ΣPUFA 512. 72 27.68
ΣPUFA:ΣSFA 0.60 0.57
n-6:n-3 0.32 0.53
*ΣSFA = saturated fatty acids; ΣMIFA = monounsaturated fatty acids; ΣPIFA = polyunsaturated fatty acids.
Table 3. Encapsulation eciency (EE%) of omega-3 and omega-6.
Fatty acid Encapsulation
eciency (EE%)
C18:3 n-3
(omega-3) 95.4 ± 0.6
C18:2 n-6
(omega-6) 92.3 ± 1.9
Omega-3 and -6 peaks can be found in the microparticles
but in less intensity when compared to in natura oil because
particles are composed of the encapsulant (stearic acid) and
oil in 1:1 (m:m) proportion. Unidentied peaks can also
be observed, probably related to impurities in the stearic
acid. No signicant dierence between encapsulation of
omega-3 and omega-6 could be found (p>0.05), which
means that the omega-3:omega-6 ratio in the particles
and in in natura oil is statistically the same (3.14 ± 0.14
and 3.11 ± 0.05, respectively). This is important since
an imbalance of the omega6:omega3 ratio as presented
by modern Western food intake is related to a number of
chronic diseases and metabolic disorders (Simopoulos,
2008). These results demonstrate that the encapsulated oil
presents the same proportion of in natura chia oil, meaning
that the microcapsules may be used to protect the oil and to
formulate products with high nutritional value.
The literature reports typical encapsulation eciency
values for omega-3 and -6 from 70 to 80% (Rodea-González
et al., 2012), 57.2 to 89.6% (Jimenez et al., 2006), 62.3
to95.7% (Carneiro et al., 2013) and 45.8% to 58% (Xu et al.,
2013), depending on the encapsulant and the encapsulation
technique. Solid lipid nano or microparticle systems are
often suitable for oil encapsulation due to the compatibility
between the oil and the encapsulant matrix. Lacatusu et al.
(2013) encapsulated sh oil in nanostructured lipid carriers
with 88.5% eciency. Unfortunately some works in the
literature did not present information on eciency values,
possibly assuming total encapsulation (Muchow et al.,
2009; Salminen et al., 2013).
Particles characterization
Optical microscopy images of chia oil-loaded particles
and blank particles (no oil added) are presented in Figures
6 and 7, respectively. Figure 8 presents infrared spectra
of in natura chia oil, chia oil-loaded particles and blank
particles. All spectra were normalized in order to allow
comparison. Figure 9 (a) presents the DSC thermograms of
the chia oil-loaded microparticles and blank microparticles
(no oil added) under nitrogen atmosphere. In Figure 9 (b)
thermograms of chia oil and chia oil-loaded microparticles
under air atmosphere are presented.
Brazilian Journal of Chemical Engineering
M. F. Souza, C. R. L.Francisco, J. L. Sanchez, A. Guimarães-Inácio,
P. Valderrama, E. Bona, A. A. C. Tanamati, F. V. Leimann and O. H. Gonçalves
666
Figure 6. Optical microscopy image of blank microparticles (no chia oil added).
Figure 7. Optical microscopy image of chia oil-loaded microparticles
Absorption band at 3010 cm-1 associated to =C-H
groups was found at the chia oil spectrum as expected
(Vidal et al., 2013). Blank particles did not show this
band since stearic acid did not present any unsaturation
on its chemical structure. This band was also present at
the oil-loaded particles but in a much lower intensity. The
decrease in intensity could be an indication of ecient
entrapment of encapsulated compounds, also corroborating
the previously results found (optical microscopy and gas
chromatography).
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Fatty acids pro le of chia oil-loaded lipid microparticles 667
In natura (before encapsulation) chia oil begins
oxidation at approximately 145°C. Grampone et al. (2013)
reported an oxidation temperature of 176°C using pure
oxygen as oxidizing atmosphere at a higher rate.This
could explain the di erence, along with discrepancies
in oil composition, as the omega-6 concentration is not
reported by the authors. The same may be concluded when
comparing to the results from Ixtaina et al. (2012), who
reported an oxidation temperature of (168.2 ± 2.8)°C. DSC
thermograms demonstrated that the encapsulation of chia
oil increased its oxidative stability since oxidation began at
approximately 259°C. This behavior was also described in
the encapsulation of oregano oil in chitosan nanoparticles
(Hosseini et al., 2013), eugenol (Woranuch and Yoksan,
2013) and also carvacrol (Keawchaoon and Yoksan, 2011)
using thermogravimetric analysis.
CONCLUSION
Chia oil was extracted by using the Bligh-Dyer method
to minimize oil degradation during extraction. UV-Vis
spectroscopy coupled to multivariate analysis (MCR-
ALS) demonstrated that no oil degradation or tocopherol
loss were expected to occur under the experimental
conditions (heating time and temperature) applied in the
hot homogenization procedure used in this work. Chia oil
wase ciently encapsulated in micrometric stearic acid
particles as demonstrated bygas chromatography, UV-Vis,
DSC and FTIR spectroscopy. Encapsulation e ciencies for
omega3 and omega6 were similar, meaning that the n-6:n-3
ratio of the particles is very close tothe one presented
byinnatura oil.Di erential Scanning Calorimetry showed
Figure 8. FTIR spectra of in natura chia oil, chia oil-loaded particles and blank microparticles (no oil added).
(a) DSC under nitrogen atmosphere. (b) DSC under air atmosphere.
Figure 9. DSC thermograms of in natura chia oil, chia oil-loaded particles and blank microparticles (no oil added).
Brazilian Journal of Chemical Engineering
M. F. Souza, C. R. L.Francisco, J. L. Sanchez, A. Guimarães-Inácio,
P. Valderrama, E. Bona, A. A. C. Tanamati, F. V. Leimann and O. H. Gonçalves
668
an increase in the oxidative stability of the encapsulated oil,
which may indicate that such microparticles are suitable to
formulate food products where long shelf life is needed or
when heating is applied during production such as in baked
products.
ACKNOWLEDGEMENTS
Authors thank CAPES, CNPq and Fundação Araucária
for the support.
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