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Received: 23 April 2020    Revised: 4 July 2020    Accepted: 15 July 2020

DOI: 10.1111/jfpp.14805

ORIGINAL ARTICLE

Microencapsulation of an essential oil (cinnamon oil) by spray

drying: Effects of wall materials and storage conditions on
microcapsule properties

Qirui Hu1 | Xia Li1 | Fang Chen1,2 | Renkou Wan1 | Cheng-Wei Yu1  | Jing Li1  |

David Julian McClements3 | Zeyuan Deng1

1
State Key Laboratory of Food Science
and Technology, College of Food Science, Abstract
Nanchang University, Nanchang, Jiangxi, Microencapsulation of cinnamon essential oil (CEO) by spray drying was carried out
China
2 to protect it from oxidation and facilitate its application within food products. Whey
School of Public Health, Nanchang
University, Nanchang, Jiangxi, China protein isolate (WPI), maltodextrin (MD), and sodium alginate were selected as wall
3
Department of Food Science, University of materials. Initial experiments were carried out to evaluate the emulsifying capacity
Massachusetts, Amherst, MA, USA
and encapsulation efficiency (EE) of the system. The optimum formulation consisted
Correspondence of 70% wall material (WPI: MD: sodium alginate = 1:3:0.01 (w/w)) and 30% CEO. The
Fang Chen and Zeyuan Deng, State Key
Laboratory of Food Science and Technology,
EE of the spray-dried CEO microcapsules formed was over 93%, and their retention
Nanchang University, 235 Nanjing East during storage at 50°C for 30 days was over 95%. Gas chromatography and liquid
Road, Jiangxi, Nanchang, China.
Email: [email protected] (F. C.) and
chromatography in conjunction with mass spectrometry were used to identify the re-
[email protected] (Z. D.) action products formed during oxidation of the CEO and possible oxidation pathways

Funding information
were proposed. The optimized formulation identified in this study may be suitable
State Key Laboratory of Food Science and for the efficiency encapsulation and stabilization of essential oils in powdered form.
Technology Free Orientation Project, Grant/
Award Number: SKLF-ZZB-201709; National Practical applications
Natural Science Foundation of China, Grant/
The optimized spray drying formulation can be applicated in processing essential oil
Award Number: 31872890
to improve their storage stability. The spray-dried product in this study can be uti-
lized in meat preservation and pastry (or biscuit) processing as food additives.

1 |  I NTRO D U C TI O N Arslan., 2011). It has also been proposed that it can be used as a
nutraceutical or medical agent due to its potential anticancer (Yang,
Cinnamon, which has been widely used historically as an herbal Zheng, Ye, Li, & Chen, 2016) and anti-inflammatory activities (Tung,
medicine, belongs to the Lauraceae family and is mainly found in Chua, Wang, & Chang, 2008). However, CEO tends to chemically de-
China and some Southeast Asian countries (Rao & Gan, 2014). grade when exposed to heat, light, or oxygen (Hermanto, Khasanah,
Cinnamon essential oil (CEO) is a volatile substance that is typically Kawiji, Manuhara, & Utami, 2016), which leads to a loss in its ben-
isolated from the bark of the cinnamontree (Ackermann, Aalto- eficial biological activities (Turek & Stintzing, 2013). Consequently,
korte, Jolanki, & Alanko, 2009). CEO contains a range of different there is a need to develop effective strategies to protect CEO from
aromatic compounds and terpenes, including cinnamaldehyde degradation during storage.
(70%–80%, w/w), acetophenone (0.3%–0.9%, w/w), benzaldehyde, Microencapsulation is the process where by a substance of
cinnamyl acetate, and camphor (Li, Kong, & Wu, 2013). In the food interest (the “core” material) is encapsulated within another sub-
industry, CEO is widely used as a spice and preservative due to its stance (the “wall material”) in the form of tiny capsules (Zuidam &
unique organoleptic, antimicrobial (Goñi et al., 2009; Zhang, Liu, Shimoni, 2010). Spray drying is a commonly used technology to
Wang, Jiang, & Quek, 2016), and antioxidant properties (Özcan & encapsulate fragrances, oils, and flavors because it is inexpensive,

J Food Process Preserv. 2020;00:e14805. wileyonlinelibrary.com/journal/jfpp |

© 2020 Wiley Periodicals LLC.     1 of 15
https://doi.org/10.1111/jfpp.14805
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2 of 15       HU et al.

reproducible, and easy to scale up (Gharsallaoui, Roudaut, Chambin, these reasons, we used WPI, sucrose esters and monoglyceride as
Voilley, & Saurel, 2007). It is particularly suitable for creating pow- mixed emulsifiers during preparation of microencapsulated CEO.
dered forms of heat-sensitive materials because the relatively short The characteristics of the wall materials are known to strongly
drying times involved (5–30 s) do not lead to excessive thermal dam- influence the functional performance of microencapsulated oils
age (Encina, Vergara, Giménez, Oyarzún-Ampuero, & Robert, 2016). (Labuschagne, 2018). For this reason, we examined the impact of wall
The potential for using spray drying to form CEO microcapsules has material (including mixed emulsifiers) composition on the formation and
been demonstrated previously, but the encapsulation efficiency (EE) stability of CEO microcapsules. Initially, the CEO was converted into an
obtained was relatively low, that is, <85% (Hermanto et al., 2016; emulsion by homogenization, and then these emulsions were converted
Pratiwi, Darmadji, & Hastuti, 2016). One of the main objectives of into a powder by spray drying. The impact of the initial formulation on
the current study was, therefore, to optimize the formulation and the physicochemical properties and stability of the CEO emulsions and
spray drying conditions so that CEO microcapsules with a higher EE microcapsules were then evaluated. In particular, possible oxidation
could be produced. Previous studies have reported that the solubil- pathways of CEO during storage were explored. This study may lead to
ity and molecular mobility of the core materials within microcapsules the development of more effective methods of protecting essential oils
depends on the nature of the wall materials used, which in turn influ- from loss during storage, as well as improving their utilization in meat
ences the EE (Gharsallaoui et al., 2007). For this reason, we paid par- preservation and pastry (or biscuit) processing as food additives.
ticular attention to optimizing the formulation of the wall materials
used to encapsulate the CEO.
Proteins, such as whey protein, have good emulsifying and 2 | M ATE R I A L S A N D M E TH O DS
film-forming properties because of their amphiphilic characteristics
(Sosa, Schebor, & Pérez, 2015). In this study, we examined the po- 2.1 | Materials
tential of using whey protein isolate (WPI) to emulsify the essential
oils. Moreover, proteins like sodium caseinate can play a role in sta- Cinnamon essential oil (CEO, ≥95% cinnamaldehyde) was purchased
bilization of emulsion as an electrosteric stabilizer (Patel, Bouwens, from Jiangxi Huitong Officinal Perfume Oil (Jiangxi, China). Whey
& Velikov, 2010), thereby, improve the qualities of microcap- protein isolate (WPI, food grade, ≥80% whey protein) was pur-
sules. Some studies, however, have shown that the microcapsules chased from Jiangxi Baiying Biotechnology (Jiangxi, China). Sucrose
formed by proteins after spray drying are deformed and shrunken ester (food grade, HLB = 15) was purchased from Hangzhou Ruilin
(Darniadi, Ho, & Murray, 2018), which may have adverse effects Chemical (Hangzhou, China). Monoglyceride (food grade, HLB = 3.6)
on the long-term stability of microencapsulated essential oils. For was purchased from Henamsiyuanshengwu Technology (Henan,
this reason, carbohydrates like maltodextrin (MD) are often used China). Maltodextrin (MD, food grade, DE16) was purchased from
as secondary wall materials to enhance the formation and storage Shandongxiwangdianfen (Shandong, China). Sodium alginate (food
stability of microcapsules (Shamaei, Seiiedlou, Aghbashlo, Tsotsas, grade) was purchased from Hebei Baiwei Biological Technology
& Kharaghani, 2017; Troya, Tupuna-Yerovi, & Ruales, 2018). Other (Hebei, China). Sodium caseinate (food grade) was purchased from
studies have shown that polysaccharides, such as sodium alginate, Shanghai Tianchen Biological Technology (Shanghai, China). Vitamin
can also be used as emulsion thickeners to enhance the properties of E oil (food grade) was purchased from Henan Together Glorious Food
microencapsulated oils (Yoo, Song, Chang, & Lee, 2006). For this rea- Ingredients (Henan, China). Acetonitrile (HPLC grade) was purchased
son, we examined the impact of using different ratios of WPI, MD, from Merck (Darmstadt, Germany). Cinnamaldehyde standards were
sodium caseinate and sodium alginate on the formation and perfor- purchased from Aladdin (Shanghai, China). Dipotassium phosphate,
mance of the wall materials in microencapsulated CEO. mono potassium phosphate, petroleum ether, ethanol, and ether
In spite of good film-forming properties, WPI possesses poorer were purchased from Xilong Scientific (Guangdong, China),
emulsion capacity than low molecular weight emulsifiers due to its
slower diffusion rate (Lam & Nickerson, 2013). Low molecular weight
emulsifiers can reduce the droplet size, increased the viscosity of the 2.2 | Preparation of microcapsules
emulsions, and facilitate the formation of strongly adsorbed film (Lu,
Kelly, & Miao, 2017). Therefore, mixed emulsifiers could be a good The procedure used to prepare the CEO microcapsules is shown
choice to enhance the properties of microencapsulated oils, which schematically in Figure 1. The aqueous phase was prepared by dis-
received little attention in related researches to our knowledge. solving the wall materials and sucrose ester in distilled water. The
Previous studies have reported that sucrose esters could enhance oil phase was prepared by mixing CEO and monoglyceride. The oil
the properties of protein-stabilized emulsion (Zhao et al., 2014). and aqueous phases were then mixed together by simple shear-
Moreover, HLB is a vital factor affecting the quality of microencap- ing. The coarse emulsion formed was then passed through a colloid
sulated oils (Liu & Yang, 2011), sucrose ester should be used in com- mill (50LA model, Shanghai Donghua High Pressure Homogenizer
bination with an emulsifier of low HLB value to obtain an appropriate Factory, Shanghai, China) and then a high-pressure homogenizer
HLB value. Monoglyceride is a lipophilic emulsifier and can modify (60-6S model, Shanghai Donghua High Pressure Homogenizer
the properties of protein-stabilized emulsions (Lu et al., 2017). For Factory, Shanghai, China) operating at 30 MPa for 3 min. The fine
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F I G U R E 1   Flow chart of cinnamon essential oil (CEO) microcapsule product preparation

TA B L E 1   Various formulations of
Wall material (g/100 g emulsion)
emulsions Ratio of CEO
Sodium Sodium WPI/MD (g/100 g
Formulation WPI MD alginate caseinate (w/w) emulsion)

1 8.4 12.6 1:1.5 9

2 7 14 1:2 9
3 5.25 15.75 1:3 9
4 5.25 15.75 0.1 1:3 9
5 5.25 15.75 0.05 1:3 9

Abbreviations: CEO, cinnamon essential oil; MD, maltodextrin; WPI, whey protein isolate.

emulsion formed was then spray-dried in a spray drying tower wall materials were mixed together to produce a total “solids” con-
(MDR-50 model, Wuxi Modern Spray Drying Equipment Co., Ltd, tent (CEO plus wall materials) in the emulsions of 30% (w/v). The
Jiangsu, China) using an inlet air temperature of 180°C, an outlet air resulting emulsions were then homogenized and spray-dried as de-
temperature of 90°C and centrifugal atomizer speed of 0.084 × g. scribed earlier. The properties of the CEO microcapsules formed
Oxidation was inhibited by adding a natural antioxidant (0.1% (w/w) were analyzed and the results used for the optimization of the wall
vitamin E) to the CEO at the beginning of the process. material formulation.

2.2.1 | The emulsifying capacity of the 2.2.3 | Identification of the functional groups of

wall materials CEO microcapsules

The emulsifying capacity of the WPI was determined by dissolving Alterations in the functional groups in the CEO due to microen-
different concentrations (3%–7% w/v) of the powdered protein into capsulation were determined by analyzing the chemical composi-
500 ml of distilled water and then adding 45 g of CEO. After being tion of the oil before and after the preparation procedure. Fourier
homogenized at 30 MPa for 3 min, the properties of the emulsions transform infrared spectroscopy (FTIR) transmission spectra were
were analyzed. taken using an FTIR spectrometer (NICOLET5700, Thermo Fisher,
Nicolet, USA) in the wavenumber range from 4,000 to 500 cm−1
at a spectral resolution of 4 cm−1 with 32 scans per sample. Four
2.2.2 | Optimization of the formulation of samples (wall materials, CEO microcapsules, CEO extracted
wall materials from the CEO microcapsules, and free CEO) were mixed with
KBr powder for FTIR measurements. Data were analyzed using
A variety of wall material formulations with different compositions the software that came with the instrument (OMNIC 8.0 and
were prepared according to Table 1. Afterwards, 30% CEO and 70% OriginPro 9.0).
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4 of 15       HU et al.

2.3 | Emulsion analysis (20 ml) was added. After filtration, the filtrate was transferred into
a weighed flask (m3) and the precipitate was extracted with diethyl
2.3.1 | Creaming stability ether (15 ml) twice. All the filtrates were combined and concentrated
using a rotary evaporators (RE -2000A model, Shanghai Yarong
The creaming stability of the emulsions was evaluated using a Biochemistry Instrument factory, Shanghai, China) at 50°C until the
method described previously (Aguiar, Silva, Rezende, Barbero, & solvent was evaporated. The flask containing the solids was weighed
Martínez, 2016), with some slight modifications. Immediately after (m4), and the surface oil was calculated: surface oil = m3 − m4.
an emulsion was prepared, a 10 ml of aliquot was transferred into a
15 ml centrifuge tube. After incubation in a water bath at 60°C for
20 min, the tubes were centrifuged at 1500 × g for 5 min. The height 2.4.2 | EE, OC, and retention rate
of the emulsified phase was measured and the creaming index was
calculated as follows: The EE, OC and retention rate (RR) of the CEO microcapsules were
calculated using the following equations, respectively:
H1
Creaming index (%) = × 100%
H0 total oil − surface oil
encapsulation efficiency (%) = × 100%
total oil

where H0 is the initial height of the emulsion and H1 is height of the

total oil − surface oil
emulsified phase. oil content (%) = × 100%
W0

2.3.2 | Droplet size and charge characteristics retention rate (%) =

total oil
× 100%
W1

The emulsions were diluted 20-times using distilled water and then
the mean droplet diameter, polydispersity index (PDI), and surface Here, W0 is the weight of the microcapsule powder and W1 is
potential (ξ-potential) were measured using dynamic light scatter- the weight of CEO in the microcapsule powder in theory (calculated
ing/electrophoresis (Zetasizer Nano ZS90, Malvern Instruments, from the known amount added at the beginning).
Malvern, UK) at a scattering angle of 90° at 25°C.

2.4.3 | Particle morphology analysis

2.4 | Microcapsule analysis
The microstructural characteristics of the microcapsules were ana-
2.4.1 | Total and surface oil lyzed by scanning electron microscopy (SEM) (Hitachi S-3400N,
Hitachi Limited, Japan). The samples were placed on an aluminum
The total oil and surface oil were measured using the Rose—Gottlieb support using a conductive tape and then coated with platinum
method with some slight modifications. using an E-1010 sputter coater (Hitachi Limited, Japan). The images
Total oil: A weighed amount of powdered microcapsules (2 g) was were taken using an acceleration voltage of 5.00 kV.
dispersed in warm distilled water (10 ml) in a 100-ml Erlenmeyer flask
and then 15 ml of ethanol was added. Afterwards, 25 ml of ether was
added and then the Erlenmeyer flask was shaken for 1 min. Petroleum 2.5 | Oxidative stability of microcapsules
ether (10 ml) was then added and the Erlenmeyer flask was plugged
and shaken for another 1 min. After stratification, the organic phase The microcapsules were stored in a constant-temperature oven set
was collected and transferred into a weighed flask (m1). Ethanol (5 ml), at 25°C, 37°C, or 50°C. A sample of pure CEO was also stored at
ether (15 ml) and petroleum (5 ml) ether were then added to the re- 50°C for comparison. Samples were removed from the oven at 1,
maining aqueous phase sequentially and the solvent extraction pro- 7, 15, 30, 60, and 90 days to analyze the alteration of RR and the
cedure was repeated three times (but only 15 ml of diethyl ether was compositions of the CEO microcapsules. The RR of the initial CEO
added the third time). Finally, all the organic phases were combined microcapsules was set as 100%.
together. The organic phase was concentrated using a rotary evapo-
rator (RE -2000A model, Shanghai Yarong Biochemistry Instrument
factory, Shanghai, China) operating at 50°C until all the solvent was 2.5.1 | Fluorescence analysis by HPLC-
evaporated. The flask containing the solids was weighed (m2) and the fluorescence detector
total oil content (OC) calculated: total oil = m2 − m1.
Surface oil: Microcapsule powder (2 g) was put into a 100-ml Changes in the level of fluorescent substances in the CEO mi-
Erlenmeyer flask. The Erlenmeyer flask was shaken slightly after ether crocapsules was determined using high-performance liquid
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TA B L E 2   Effects of WPI concentration on emulsion characteristics

Concentration (%) Ratio of WPI/CEO (W/W) Creaming index (%) Zeta potential (mV) Mean droplet size (nm) PDI
a c d
3 3:9 90.7 ± 2.3 −10.70 ± 0.14 347 ± 12 0.34 ± 0.10a
b ab c
4 4:9 95.4 ± 1.8 −13.70 ± 0.42 257.0 ± 5.5 0.25 ± 0.01a
5 5:9 100.0 ± 0.0 c −18.50 ± 3.25a 233.5 ± 2.5b 0.28 ± 0.01a
c a a
6 6:9 100.0 ± 0.0 −17.10 ± 0.14 197.6 ± 6.2 0.35 ± 0.04a
7 7:9 100.0 ± 0.0 c −14.35 ± 0.49ab 178 ± 12a 0.52 ± 0.06b

Note: Means followed by different letters within each column are significantly different (p < .05).
Abbreviations: CEO, cinnamon essential oil; PDI, polydispersity index; WPI, whey protein isolate.

chromatography (Agilent 1260 HPLC system, Agilent Technologies, and a helium carrier gas flow rate was 1.56 ml/min. The ion source
USA) equipped with a fluorescence detector (FLD). The column was was set at 230°C and quadrupole mass selective detector at 150°C
an Agilent Zorbax Edipse plus C18 (250 mm, 4.6 mm, 5 mm) col- was operated in total ion scan mode from 35 to 500 m/z.
umn. The elution phases used were: Phase A—0.1% (v/v) aqueous
formic acid; Phase B—acetonitrile modified with 0.1% formic acid.
Elution was carried out in gradient mode as follows: 0–5 min (80%- 2.6 | Statistical analysis
87%, B), 5–9 min (87%–90%, B), 9–12 min (90%-95%, B), 12–15 min
(95%–100%, B), 15–38 min (100%, B). The injection volume was 3 μl Measurements of the emulsion or microcapsule properties were
and the column temperature was set at 25°C. The flow rate was set performed in triplicate. The resulting data were then evaluated
at 0.5 ml/min. The excitation and emission wavelengths were set at using analysis of variance (ANOVA) using SPSS statistical software
450 nm and 530 nm, respectively. (version 16.0) and statistically significant tests were analyzed by the
Duncan test and Tukey test at p < .05.

2.5.2 | Compositions of oxidized CEO

3 | R E S U LT S A N D D I S CU S S I O N
The composition of the CEO after being oxidized was determined
using liquid chromatography coupled with mass spectrometry. The 3.1 | Effects of WPI/CEO ratio on emulsion
UPLC-electrospray ionization source (ESI)-QTOF-MS/MS analy- characteristics
sis was performed on an Agilent 1290 Infinity LC system (Agilent
Technologies, USA) coupled with an Agilent 6430 triple quadru- The characteristics of emulsions prepared using different WPI con-
pole mass spectrometer (Agilent Technologies, USA). The chroma- centrations are summarized in Table 2. Stable emulsion is requisite
tographic separations were performed on a Shim-pack GIST C18 for spray drying. The creaming index showed that the WPI-CEO
column (2.1 mm, 75 mm, 2 μm). The flow rate was 0.2 ml/min, and emulsion was kinetically stable (creaming stability = 100%) when the
the injection volume was 5 μL. The mobile phase consisted of 0.1% ratio of WPI/CEO was ≥5:9 (w/w).
formic acid (A) and acetonitrile modified with 0.1% formic acid (B). Higher is the absolute value of ξ-potential within 30 mV, more sta-
A linear gradient was applied as follows: 20%–25% B at 0–10 min; ble is the emulsion (Cano-Sarmiento et al., 2018). The ξ-potential of
25%–80% B at 10–25 min; 80%–100% B at 25–35 min; 100% B at the WPI emulsions varied from −18.5 mV to −10.7 mV with the highest
35–40 min and 20% B at 40–41 min. negative value being obtained at a ratio of WPI/CEO of 5:9 (Table 2).
An ESI interface was set in positive mode. The conditions were as The mean droplet diameter became smaller as the WPI concen-
follows: capillary voltage, 4 kV; drying gas flow, 10 L/min; gas tem- tration increased, changing from around 350 to 178 nm when the
perature, 350°C; nebulizer pressure, 40 psi; and fragmentor voltage, ratio of WPI/CEO increased from 1:3 (w/w) to 7:9 (w/w). The PDI
135 V. The potential biomarkers were analyzed by tandem mass of a colloidal dispersion is a measure of the range of particle sizes
spectrometry (MS/MS) in the Q‑TOF mode. Nitrogen was used as present, with PDI < 0.3 meaning a fairly tight distribution (Salleh,
the collision gas at collision energies of 30 eV. Data were collected in Hamid, Bustami Effendi, & Jamil, 2012). The PDI of the WPI-CEO
total ion scan mode from 50 to 1,000 m/z. emulsion was lower than 0.3 when the ratio of WPI/CEO was 4:9
GC-MS analysis was on an Agilent 6890N Infinity GC sys- and 5:9 (w/w). These two emulsions, therefore, had the narrowest
tem (Agilent Technologies, USA)equipped with an Agilent particle size distributions, which can also be seen in Figure 2.
19091S-433HP-5 ms column (0–325°C; 30 m × 250 μm × 0.25 μm) The emulsion with a mass ratio of WPI/CEO = 5:9 had a high
and operated in a program with an initial temperature of 60°C for electrical charge, small droplet size, narrow particle size distribution,
2 min, rate of 8°C/min and with a final temperature of 280°C for and good creaming stability. Adding any extra protein only led to
10 min. The injection volume was 1 μl and the injector port was op- marginal improvements in emulsion stability. For this reason, we
erated at 270°C. The carrier gas was helium followed by a 20:1 split used the WPI/CEO = 5:9 system in all the subsequent studies.
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F I G U R E 2   Particle size distributions of droplets in cinnamon essential oil (CEO) emulsions prepared at weight ratios of WPI/CEO = (a)
1:3, (b) 4:9, (c) 5:9, (d) 2:3, (e) 7:9. WPI, Whey protein isolate

3.2 | Effects of various wall material formulations TA B L E 3   Effects of various formulations on microencapsulation

on microencapsulation Formulation EE (%) OC (%) RR (%)

1 84.18 ± 0.52a 20.70 ± 0.15a 73.77 ± 0.56a

3.2.1 | EE of microcapsules
b ab
2 86.55 ± 0.68 21.02 ± 0.23 73.93 ± 0.42a

To improve the encapsulation properties of the microcapsules, 3 87.28 ± 0.74b 21.42 ± 0.18b 73.90 ± 0.38a

b c
maltodextrin was used as a secondary wall material. The impact 4 87.92 ± 0.46 22.06 ± 0.28 78.12 ± 0.39b

of utilizing different mass ratios of MD-to-WPI on the microcap- 5 89.52 ± 0.52c 22.06 ± 0.26c 80.12 ± 0.41c
sule properties was determined. The microencapsulation quality Note: Means followed by different letters within each column are
was evaluated by calculating the EE, OC, and RR values (Table 3). significantly different (p < .05).
Comparing Formulations 1–3, Formulation 3 had the highest EE Abbreviations: EE, encapsulation efficiency, OC, oil content of the
(87.3%), OC (21.4%) and RR (73.9%) values. The EE and OC increased cinnamon essential oil microcapsule, RR, retention rate.

with decreasing WPI/MD ratio, however, the RR was not significantly

different. A similar trend has been reported for the EE of microcap-
sules when the WPI/MD ratio was varied by other researchers (Koç In conclusion, Formulation 5 (WPI: MD: sodium algi-
et al., 2015). When WPI and MD are used as wall materials in com- nate = 1:3:0.01 (w/w)) gave a better encapsulation quality than any
bination, the curing speed of the wall materials during spray drying of the other formulations tested.
decreases when the ratio of WPI/MD becomes too high, which leads
to lower EE or OC of microcapsules containing volatile core materials
(Sheu & Rosenberg, 1998). 3.2.2 | Particle morphology of microcapsules
Comparing formulations 3 and 5, we concluded that the quality
of the microcapsules became significantly better when sodium al- Micrographs of the microcapsules were acquired using scanning
ginate was added (Table 2): EE increased from 87.3% to 89.5%; OC electron microscopy (Figure 3). In all formulations, the microcap-
increased from 21.4% to 22.1% and RR increased from 73.9% to sules existed as single discrete particles, which suggested that the
80.1%. However, there was no significant improvement in EE after level of CEO on the surfaces of the microcapsules was relatively low.
sodium caseinate was added (Formulation 4). A possible explanation Indeed, previous studies have shown that high levels of free oil on
is that sodium caseinate mainly acts as an emulsifier, and there was the surfaces of spray-dried particles leads to agglomeration (Dantas,
already sufficient whey protein present to stabilize the emulsions Pasquali, Cavalcanti-Mata, Duarte, & Lisboa, 2018). This effect is
(Ixtaina, Julio, Wagner, Nolasco, & Tomás, 2015). The addition of so- probably due to hydrophobic or capillary attraction between the oily
dium alginate increases the viscosity of the emulsions, which may patches on the surfaces of the powder particles. In a previous study,
have promoted a faster solidification process of the wall materials where avocado oil was encapsulated in powders formulated using
during spray drying, thereby decreasing the amount of volatiles lost different WPI/MD ratios, it was reported that the microcapsules
(Lević et al., 2015). Sodium alginate addition, therefore, seemed to aggregated at all WPI/MD ratios used (Bae & Lee., 2008), which is
improve the encapsulation quality of the microcapsules prepared different from out study. This difference may have been due to dif-
from MD and WPI. ferences in the nature of the two kinds of core material used in the
HU et al. |
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F I G U R E 3   Scanning electron
microscope micrographs of cinnamon
essential oil microcapsules prepared with
weight ratios of WPI:MD = 1:1.5 (a and
b), WPI:MD = 1:2 (c and d), WPI:MD = 1:3
(e and f), WPI:MD:SC = 1:3:0.02 (g and h)
and WPI:MD:SA = 1:3:0.01 (i and j). WPI,
Whey protein isolate

two studies. CEO mainly consists of aromatic compounds, while avo- Previous researchers have attributed this effect to the formation of
cado oil is mainly composed of aliphatic compounds. a softer, more porous crust during spray drying when maltodextrin is
In addition, the electron micrographs showed that irregu- present (Darniadi et al., 2018). Compared with Formulations 1, 2, and
lar-shaped particles were formed at high WPI/MD ratios, but more 3, less pores were observed in Formulation 5. The crust of the micro-
smooth spheroids were formed at low WPI/MD ratios (Figure 3). capsules appeared denser after sodium alginate was added, which
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8 of 15       HU et al.

should slow down the volatilization of CEO. Previous study also CEO, with emulsifiers (sucrose ester/monoglyceride = 3:1 (w/w)) being
revealed a fact that sodium alginate combining with other wall ma- added at 0.1 g per 100 g CEO. Then an emulsion was formed with 40%
terials could improve the porosity (Belscak-Cvitanovic et al., 2015). (w/v) solid content (wall materials plus CEO) at 55°C and pH 6.5.
Sodium alginate made contributions to homogeneity of microcap- Under these optimum conditions, the EE of the CEO microcap-
sules and other wall materials could occupy the interstitial spaces of sules was 93.40 ± 0.21%, which was relatively high in comparison
the microcapsules. The difference in the morphology of the micro- to other reports. The EE of CEO microcapsules prepared by Pratiwi
capsules may also explain the higher EE, OC and RR of Formulation 5. et al. (2016) and co-workers ranged from 40.3% to 84.6%. The EE
of CEO microcapsules formulated with MD and arabic gum was re-
ported to range from 59.8% to 70.7% (Hermanto et al., 2016). This
3.3 | The optimized microencapsulation process advantage in EE, therefore, implies that proteins might be better for
encapsulating CEO than carbohydrates like arabic gum.
3.3.1 | The selection of optimized
microencapsulation process
3.3.2 | FTIR features of spray-dried microcapsules
Initially, the main factors effecting the emulsification process, such
as solid content, emulsification temperature, emulsion pH, and mixed Fourier transform infrared spectroscopy experiments were carried
emulsifier formulation, were optimized using a single-factor test out in order to analyze molecular changes during the spray drying
(Figure S1 and Table S4) and orthogonal test (Tables S1–S3). The mi- process, as well as to detect chemical reactions between the wall
croencapsulation conditions for formation of the CEO microcapsules materials matrices and the CEO.
were then optimized. The optimum formulation was found to be 70% The presence of cinnamaldehyde in the microcapsules was
wall material (WPI: MD: sodium alginate = 1:3:0.01 (w/w)) and 30% supported by the FTIR measurements (Figure 4a(i)). There was a

F I G U R E 4   Infrared spectra of (a) the cinnamon essential oil (CEO) microcapsules components, (b) CEO before and after
microencapsulation
HU et al. |
      9 of 15

weak peak at 3028.24 cm−1, which can be associated with =C–H 3.4 | Oxidative stability
stretching vibrations on the benzene ring. The peaks at 1625.11 to
1450.47 cm−1 were attributed to the C=C stretching vibration of 3.4.1 | RR of CEO during storage
the benzene skeleton. Additionally, the peaks at 1,220 to 950 cm−1
were attributed to the =C–H out-of-plane bending vibration of the The main aim of this study is to protect CEO from oxidation using
−1
benzene ring and the peak at 747 cm was attributed to the =C–H microencapsulation. For this reason, the oxidative stability of the
in-plane bending vibration. The strong peak at 1676.56 cm−1 was as- microcapsules was measured during storage. The RR of the CEO mi-
sociated with a C=O stretching vibration and the two weak peaks at crocapsules decreased as the storage time increased (Table 4). As ex-
2,820 and 2,720 cm−1 were attributed to the =C–H stretching vibra- pected, the CEO microcapsules stored at 25°C (room temperature)
tion of the aldehyde group. were the most stable ones, with the RR value only falling to 95.9%
In Figure 4a(ⅲ), the broad peak at 3,420 cm−1 was assigned to after 90-days storage. Conversely, the CEO microcapsules stored
the O-H stretching vibration of the protein carboxyl, the peaks at 50°C were the most unstable, with the RR value falling to below
at 1,850 to 1,650 cm−1 were attributed to the C=O stretch- 87.1% over the same period. Previous researchers have reported
−1
ing vibration and the peaks at 1,100 to 1,000 cm were due to that both surface and total oil in CEO microcapsules formed using
the C–O stretching vibration. These peaks could also be seen MD/arabic gum (1:1, w/w) as wall materials decreased during stor-
in Figure 4a(ⅱ). What is more, the characteristic absorption age (Pratiwi et al., 2016). Moreover, they reported that the loss of oil
peaks of cinnamaldehyde at 1,620 and 1675 cm−1 still existed in increased with increasing storage temperature. As a result, the RR
Figure 4a(ⅱ). It followed that the infrared spectrum of (ⅱ) was was reduced by almost 25% after 28-days storage at 50°C (Pratiwi
a simple superposition of (ⅰ) and (ⅲ). Meanwhile, there was no et al., 2016), which suggested the WPI provided better protection to
significant difference between the infrared spectra of CEO before CEO than arabic gum during storage.
and after microencapsulation (Figure 4b). To conclude, no appar-
ent chemical change of the CEO due to microencapsulation could
be detected by the FTIR method. 3.4.2 | Predicting shelf life
In a previous study, where vitamins A, D3, E, K 2, curcumin, and
coenzyme Q10 were dispersed in tuna oil, IR analysis indicated that As described previously, we fitted zero- and first-order reaction
there was no chemical bonding between the lipids and the wall models to the RR data to estimate the shelf life of the CEO micro-
material and that there was no observable lipid oxidation (Wang, capsules (Hu, Liu, Hao, Zhang, & He, 2013). The zero-order reac-
Vongsvivut, Adhikari, & Barrow, 2015). In another study, using atten- tion model had a higher correlation coefficient than the first-order
uated total reflectance infrared spectroscopy, it was reported that reaction one at 25 and 50°C and the correlation coefficients of both
folic acid was only physically entrapped inside starch capsules during models were close at 37°C (Table 5). It was, therefore, reasonable to
microencapsulation (Perez-Masia et al., 2015). conclude that the loss of CEO followed a zero-order kinetics model.

TA B L E 4   Retention rates of essential oil at different storage temperatures of microcapsules

Temperature 1 day 7 days 15 days 30 days 60 days 90 days

a,A a,A a,A a,B a,C
25°C 100 ± 0% 99.80 ± 0.11% 99.76 ± 0.13% 98.27 ± 0.15% 97.02 ± 0.14% 95.86% ± 0.11a,D
b,A a,A b,A a,B a,C
37°C 99.76 ± 0.1% 99.58 ± 0.13% 99.44 ± 0.11% 98.38 ± 0.14% 96.87 ± 0.14% 92.60 ± 0.13%b,D
50°C 99.69 ± 0.1%b,A 98.72 ± 0.15%b,B 97.87 ± 0.12%c,C 96.92 ± 0.13%b,D 94.02 ± 0.12%b,E 87.10 ± 0.11%c,FA

Note: Means followed by different capital letters within each row are significantly different (p < .05).
Means followed by different small cases within each column are significantly different (p < .05).

TA B L E 5   The kinetic models of

First-order kinetics reaction
CEO loss during storage at different
Zero-order kinetics reaction model model
temperature
Temperature Kinetics model R2 Kinetics model R2

25°C y = 0.0485t − 0.0763 .9771 y = 0.2288e 0.037t .8154

37°C y = 0.0761t − 0.3194 .9327 y = 0.3333e 0.0365t .9523
0.0335t
50°C y = 0.1292t − 0.0493 .9459 y = 0.7876e .8253
2
Note: R , correlation coefficient; t, the storage time (day); y, the loss of CEO (%).
Abbreviation: CEO, cinnamon essential oil.
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10 of 15       HU et al.

The time for the RR to decrease to 50% of its initial value was used as Changes in the composition of the CEO during storage were
a measure of the shelf life of the samples. The shelf life of the micro- quantified using UPLC-ESI-QTOF-MS/MS and GC-MS analysis. Nine
capsules was estimated to be 1,032 days at 25°C, 662 days at 37°C, substances were identified by UPLC-ESI-QTOF-MS/MS (Table 6 and
and 387 days at 50°C. The storage stability of the microcapsules Figure 6) and seven substances were identified by GC-MS (Table 7
was, therefore, better than that reported for the WPI-gum arabic and Figure 7). Three substances were identified by both methods:
system mentioned ealier (Pratiwi et al., 2016). This effect might be cinnamaldehyde, cinnamic acid, and benzyl cinnamate. The sub-
related to the fact that a denser (less poriferous) crust was formed stances identified by the two methods did not, therefore, fully
in the microcapsules prepared from WPI, maltodextrin, and sodium match, which might be because volatile substances with low polarity
alginate (Figure 3). did not fully ionized in the ESI, which hindered their detection in
the LC-MS system (Vaiano, Mari, Busardo, & Bertol, 2014). Another
possible reason for this phenomenon is that high boiling point sub-
3.4.3 | Oxidative product analysis stances were not fully volatilized in the GC.

The oxidative stability of the CEO was monitored using HPLC com-
bined with fluorescent detection (Figure 5). The overall fluorescence 3.4.4 | Possible oxidation pathway
intensity, as well the number of different fluorescent substances
generated, increased as the storage time and temperature increased. Our results indicate that the CEO chemically degraded during stor-
As expected, the fluorescent substances present in the free and mi- age at elevated temperatures, no matter it was microencapsulated or
croencapsulated CEO were the same before storage. However, they not. Therefore, the possible oxidation pathway should be analyzed
were different after storage. In particular, the fluorescence intensity for exploring a way to inhibit the oxidation reactions in future.
of the free CEO was appreciably higher than that of the encapsu- Previously, it has been reported that fatty acids, alkanes, ter-
lated CEO stored under similar conditions, indicating that microen- penes, and phenols can generate free radicals in the presence of
capsulation protected the CEO during storage. light, heat, or oxygen, which promote oxidation of essential oils

F I G U R E 5   (a) Free cinnamon essential oil (CEO) stored at 50°C for 1 day, (b) CEO stored at 50°C for 1 month, (c) microencapsulated
CEO stored at 50°C for 1 day and (d) microencapsulated CEO stored at 50°C for 1 month were analyzed by high-performance liquid
chromatography (HPLC) with Fluorescence Detection (FLD)
HU et al. |
      11 of 15

TA B L E 6   Partial ingredient identification of CEO from UPLC-ESI-QTOF-MS/MS

No. of Molecular [M-H]+

peak Compound formula (m/z) fragment ions (m/z) Molecular structure

2 Styrylglyoxal C10H8O2 161.0584 133.0682, 115.0533, 105.0325, 103.0534,

77.0378

3 Benzylideneacetone C10H10O 147.0425 131.04, 103.05, 77.03

4 Cinnamic acid C 9 H 8 O2 149.0582 131.04, 103.05, 77.0379, 51.02

6 Cinnamaldehyde C 9H 8 O 133.0682 115.0538, 105.06, 103.05, 91.05, 89.03,

79.03, 77.03, 65.03, 55.01

7 2-Naphthyl benzoate C17H12O2 249.0889 231.0891, 115.0531, 105.0321, 77.0375

8 Peroxycinnamic C18H14O2 295.0940 131.0475, 103.0527

anhydride

14 Benzyl cinnamate C16H14O2 239.1098 221.0943, 202.0753, 193.0989, 178.0753,

161.0579, 133.0634, 115.0526,
105.0320, 91.0526, 77.0371

18 Trans,trans- C17H14O 235.1098 215.0832, 202.0755, 157.0633, 128.0600,

dibenzylideneacetone 115.0524, 105.0317, 91.0525, 77.0370,
65.0379

19 2,3-Diphenyl-2- C18H16O 249.1252 215.0835, 128.0602, 115.0526, 105.0315,

cyclohexene-1-ketone 91.0526, 77.0375, 65.0379

Abbreviations: CEO, cinnamon essential oil; ESI, electrospray ionization source.

F I G U R E 6   Ultra-efficient liquid mass flow chart of cinnamon essential oil (CEO) under accelerated oxidation for 1 month
12 of 15      | HU et al.

(Choe & Min, 2006; Turek & Stintzing, 2013). Aromatics, aldehydes of cinnamon oil (Clinton et al., 1975). Initiated by heat or light, the
and ketones can also generate free radicals in the presence of heat cinnamaldehyde decomposes into radical 1 and peroxyl radicals 2 in
or light, which can promote oxidation of oils in the presence of oxy- the presence of oxygen. Two molecules of peroxyl radicals 2 turned
gen (Clinton, Kenley, & Traylor, 1975; Gould, Baretz, & Turro, 1987; into two molecules of radical 8 with release of one molecule of oxy-
Loury, 1972; Zaikov, Howard, & Ingold, 1969). Based on these re- gen. The radical 8 were so unstable that they bond with themselves
actions, a potential oxidation pathway of CEO was postulated to form peroxycinnamic anhydride or continued to break down
(Figure 8). into radical 5 (Clinton et al., 1975). Peroxyl radicals 2 could capture
Cinnamaldehyde and acetophenone (the main components in the hydrogen of cinnamaldehyde as described previously (Zaikov
CEO (Li et al., 2013)) are believed to be key players in the oxidation et al., 1969), resulting in the formation of peroxycinnamic acid 4 and
pathways. Previously, it has been postulated that peroxycinnamic radical 3. The formation of trans,trans-dibenzylideneacetone resulted
anhydride is one of the reaction products formed during oxidation from the binding of radical 3 and radical 5. A disproportionation re-
action could happen between peroxycinnamic acid and cinnamalde-
TA B L E 7   Partial ingredient identification of CEO from GS-MS hyde and generate cinnamic acid. It has been postulated that there are
Retention time Compound Qual also other possible ways for peroxyacid to be cleaved (Loury, 1972).
a Peroxycinnamic acid 4 might decomposed into hydroxyl radical, rad-
5.688 Benzaldehyde   96%
ical 5 and carbon dioxide. Phenylacetaldehyde was generated after
11.565 Cinnamaldehydea  97%
the binding of hydroxyl radical and radical 5, which was followed by
14.162 Cinnamic acida  97%
a keto-enol tautomerism. The mechanism responsible for phenylac-
22.070 Quinolineb  91%
etaldehyde turning into radical 7 can be attributed to the following
23.154 Benzyl cinnamatea  99%
pathway: cinnamaldehyde-radical 1—peroxyl radical 2—radical 8—
24.218 1,4-Diphenyl-1,4-butanedioneb  90% radical 5. Radical 7 and radical 8 bound with each other, which was
24.350 Benzocyclobuteneb  59% followed by the generation of benzyl cinnamate. Phenylacetaldehyde
Abbreviation: CEO, cinnamon essential oil. could also decompose into radical 7 and radical 9. The formation of
a
Compounds were identified by being compared with retention time styrylglyoxal was based on the combination of radical 9 and radical 1.
and results of GC-MS of standards. Acetophenone could be decomposed into radical 10 and methyl
b
Compounds were identified according to database. radical (Glazebrook & Pearson, 1939). The methyl radical bound with

F I G U R E 7   GC-MS chromatogram of cinnamon essential oil (CEO) under accelerated oxidation for 1 month
HU et al. |
      13 of 15

F I G U R E 8   Possible oxidation pathways of cinnamon essential oil (CEO) during storage

radical 1, which resulted in the formation of benzylideneacetone. C O N FL I C T O F I N T E R E S T

Radical 10 could attack acetophenone and become benzaldehyde The authors have declared no conflicts of interest for this article.
(Heller & Gordon, 1956), with radical 11 also forming. The genera-
tion of 1,4-diphenyl-1,4-butanedione was attributed to the binding AU T H O R C O N T R I B U T I O N S
of radicals 11. Qirui Hu has made substantial contributions to analysis and interpre-
tation of data and was involved in drafting the manuscript. Xia Li and
Renkou Wan have made substantial contributions to conception and
4 | CO N C LU S I O N design, and acquisition data. Zeyuan Deng has made contributions
to conception and design of the study and was involved in revising
This study examined the impact of wall material composition on manuscript critically for important intellectual content. Fang Chen,
the microencapsulation of CEO by spray drying. The WPI-to- Cheng-wei Yu, Jing Li and David Julian McClements were all involved
maltodextrin ratio had to be optimized to create microcapsules in revising manuscript critically for important intellectual content.
with good particle and encapsulation characteristics. The addition
of sodium alginate improved the properties of the CEO microcap- ORCID
sules. For this reason, an optimized mixture of WPI, maltodextrin, Cheng-Wei Yu  https://orcid.org/0000-0001-5337-9200
and sodium alginate was identified as a good wall material for micro- Jing Li  https://orcid.org/0000-0002-2271-7761
encapsulation of CEO. The optimized formulation (including mixed Zeyuan Deng  https://orcid.org/0000-0001-5650-1507
emulsifiers) led to a high EE (>93%) and high retention (>95%) of
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