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PACKAGING TECHNOLOGY AND SCIENCE

Packag. Technol. Sci. 2013; 26: 3138


Published online 13 March 2012 in Wiley Online Library (wileyonlinelibrary.com) DOI: 10.1002/pts.1964

Antioxidant Effects of Sesamol Released from Polymeric Films on


Lipid Oxidation in Linoleic Acid and Oat Cereal
By Xuntao Zhu, Karen Schaich, Xi Chen and Kit Yam*
Department of Food Science, School of Environmental and Biological Sciences, Rutgers, The State University of New
Jersey, 65 Dudley Rd., New Brunswick, NJ 08901-8520, USA

The antioxidant effects of sesamol lms were evaluated using a food simulant (linoleic acid) and a real food
(oat cereal). Sesamol was melt blended with high density polyethylene, linear low density polyethylene and
ethylene-vinyl acetate resins using co-extrusion to produce sesamol lms of multilayer structure; for
comparison, lms containing butylated hydroxytoluene (BHT) or no additive (as control) were also produced.
At least 60% of the initial amount of sesamol remained in the lms after extrusion. The release of sesamol
from the sesamol lms was about six times faster at 30 C than at 10 C. The antioxidant effectiveness of
sesamol and BHT was evaluated on the basis of induction period of lipid oxidation, conjugated dienes (for
linoleic acid), hexanal (for oat breakfast) and sensory evaluation. Compared with the control lm, the sesamol
lms extended the induction period of linoleic acid by ve and eight times at 40 C and 23 C, respectively.
After 12 month storage at 23 C, hexanal formation was 59% less in cereal packaged with sesamol lms than
that packaged with control lm. Rancid odours were detected in cereal packaged with control lms, but not
with sesamol or BHT lms. The incorporation of sesamol had only slight effects on tensile properties and
transparency. Copyright 2012 John Wiley & Sons, Ltd.
Received 9 January 2012; Revised 26 January 2012; Accepted 13 February 2012
KEY WORDS: sesamol; lipid oxidation; controlled release packaging

INTRODUCTION
Lipid oxidation is a major deterioration mode limiting shelf lives of fat-containing foods. This free
radical chain reaction, once started by initiators such as light and metal, keeps itself going indenitely
in a series of hydrogen abstraction that can potentially involve hundreds of lipid molecules from a
single initiation.1 Alkoxyl radicals from decomposition of intermediate hydroperoxides undergo
scission reactions and form aldehydes and ketones that are responsible for the characteristic rancid
off-odours and avours of rancid products. Reactions of lipid free radicals and secondary oxidation
products with proteins and other food components degrade functionality, cause loss of nutritional
value and even generate toxic compounds,2 all of which shorten the shelf life of food products.35
To inhibit lipid oxidation, antioxidants are traditionally added into food formulation to quench lipid
free radicals, stop chain reactions and extend shelf life.4
An innovative technology for adding an antioxidant into food using the package as a delivery system is
known as controlled release packaging (CRP)5 in which the antioxidant is incorporated into the package
and then released onto the food surface, where most lipid oxidation occurs, in continually replenished
small amounts to retard lipid oxidation.6 For a volatile antioxidant, the release involves the sequential
steps of diffusion of the antioxidant through the polymer bulk phase toward the polymer surface,
* Correspondence to: Kit Yam, Department of Food Science, School of Environmental and Biological Sciences, Rutgers,
The State University of New Jersey, 65 Dudley Rd., New Brunswick, NJ 089018520, USA.
E-mail: yam@aesop.rutgers.edu
Copyright 2012 John Wiley & Sons, Ltd.

32

X. ZHU ET AL.

evaporation of the antioxidant from the polymer surface to the package headspace and sorption of the
antioxidant onto the food surface.
Butylated hydroxytoluene (BHT) is a synthetic volatile antioxidant that has long been added to
packages of dry foods such as breakfast cereal.7,8 However, the current trend is to replace BHT and
other potentially toxic synthetic additives with natural compounds, as the society prefers natural
products and greener labels.8 Sesamol, an important component from sesame seed and oil, is a potent
antioxidant with chemical structure (Figure 1) containing a benzodioxole group responsible for solubility
and a phenolic group responsible for antioxidant activity.9 Sesamol has been shown to be a highly
effective antioxidant for inhibiting oxidation in lard10 and food oils11 and for stabilizing oils against
thermal degradation during frying12 and microwave heating.13 It has been shown that 100 mg/kg sesamol
and tocopherol reduced lipid oxidation and irradiation-induced off-avours in ground beef14 and 200 mM
sesamol stabilized irradiated pork homogenates and patties.15 Because sesamol is a highly effective
natural antioxidant, relatively inexpensive and available compared with other natural antioxidants,
it is a good candidate to replace synthetic antioxidants such as BHT in CRP applications.
The objective of this study was to evaluate the antioxidant effectiveness of sesamol lms to inhibit lipid
oxidation in packaged foods. To achieve this objective, the following tasks were performed: (a) determine
the release kinetics of sesamol from the polymer lms into headspace, (b) evaluate the antioxidant
effectiveness of sesamol lms on a food simulant (linoleic acid) and a real food (oat-based breakfast
cereal), and compare it with those of the control (no antioxidant) and BHT lms and (c) evaluate the
effects of incorporating sesamol on the tensile properties and transparency of the lms.
MATERIALS AND METHODS
Materials
Barefoot resins (containing minimum plastics additives) of high-density polyethylene (HDPE), linear
low-density polyethylene (LLDPE) and ethylene-vinyl acetate (EVA) were provided by Berry Plastics
(Chippewa Falls, WI, USA). BHT (99%), hexanal (99%) and 2-methyl-pentanal (98%) were purchased
from Sigma-Aldrich Co. (Milwaukee, WI, USA). Sesamol (98%), linoleic acid (99%) and all organic
solvents (high-performance liquid chromatography grade) were purchased from Fisher Scientic
Inc. (Suwanee, GA, USA). A commercial oat-based cereal was supplied by a major food company,
not named for condentiality reason. The cereal contained only endogenous antioxidants with no
additional antioxidants in the formulation.
Film production
Sesamol resin concentrates were prepared by melt blending sesamol with LLDPE, HDPE and EVA
resins using a twin-screw extruder. The resin concentrates were then dry mixed with appropriate
amounts of virgin resins using a ribbon mixer to dilute the sesamol concentration to 1000 or
2000 mg/kg. The lms in Table 1 were produced using a co-extruder (Davis-Standard, Pawcatuck,
CT, USA) operating at a die temperature of 221 C and a screw speed of 70 rpm. Films containing
no antioxidant (as control) and BHT were also produced for comparison purpose. The lm structures
are shown in Figure 2 in which the thickness ratio of the three layers was approximately 20/60/20.

Figure 1. Structure of sesamol.


Copyright 2012 John Wiley & Sons, Ltd.

Packag. Technol. Sci. 2013; 26: 3138


DOI: 10.1002/pts

ANTIOXIDANT EFFECT OF SESAMOL

33

Table 1. Extractable antioxidants and layer structures of lms used in this study.
Film
A
B
C

Antioxidant

Initial loading (mg/kg)

Extractable
antioxidant (mg/kg)

Film structure (layers)

Sesamol
Sesamol
BHT

2000
1000
2000

1218  11
646  18
1606  29

LLDPE/HDPE/HDPE
HDPE/HDPE/EVA
HDPE/HDPE/EVA

Film A

Film B

Film C

LLDPE

HDPE

HDPE

HDPE+sesamol

HDPE+sesamol

HDPE+BHT

HDPE

EVA

EVA

Figure 2. Structure of antioxidant lms.


Antioxidant retention in lms
The amounts of sesamol and BHT retained in the lms were determined by extraction with methylene
chloride using the method of Obinata.16 Films were cut into approximately 1  1 cm square pieces and
immersed into 40 ml methylene chloride inside a 250 ml Erlenmeyer ask. The ask was rotary agitated
at 100 rpm at 37 C for 24 h in a shaking incubator (C25KC, New Brunswick Scientic Inc., New
Brunswick, NJ, USA). Sesamol and BHT concentrations in the solvent were quantied using gas
chromatography (GC; Agilent 6890N, Agilent Inc., Santa Clara, CA, USA) with ame ionization detector
(FID) and HP-5 capillary column (60 m, ID 0.32 mm, Agilent Inc., Santa Clara, CA, USA). One
microlitre sesamol or BHT samples was injected into the GC by split injection (split ratio 10:1). The initial
oven temperature was 40 C (held 1 min). The oven temperature was raised at a rate of 8 C/min to 180 C
(held 1 min) then to 250 C (held 5 min) with nitrogen as the carrier gas at a ow rate of 1 ml/min.
Concentrations of sesamol and BHT were calculated from standard curves prepared from pure sesamol
(98%) and BHT (99%).
Release of sesamol from lms into package headspace
Film A was cut into square pieces (20  20 cm). The squares were then suspended in one-quart
(0.946 l) canning jars by attaching them to the underside of the jar lids with adhesive tapes and strings.
The experiment setup was similar to that shown in Figure 3, except no food stimulant (linoleic acid)
was placed in the jars. The lids were sealed with silicone gel to prevent gas leak. The jars were

sesamol film
linoleic acid

Figure 3. Experimental setup for testing antioxidant effect of sesamol lms on linoleic acid.
Copyright 2012 John Wiley & Sons, Ltd.

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DOI: 10.1002/pts

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X. ZHU ET AL.

incubated in an environmental chamber (C25KC, New Brunswick Scientic Inc., New Brunswick,
NJ, USA) at 10 C and 30 C in the dark and were periodically removed for analysis. One gram
lm sample from each square lm was cut out, and the amount of sesamol retained in the
lm was measured by the method of solvent extraction mentioned previously. The amount of
sesamol released was calculated by subtracting the amount of retained sesamol from the initial
sesamol in the lm.
Antioxidant effect of sesamol lms on linoleic acid as food simulant
The experimental setup shown in Figure 3 (adopted from Jongjarionrak and Nerin)17,18 was used to test
the effect of released sesamol on inhibiting lipid oxidation in a food simulant, linoleic acid. One gram of
lm A and control lm (with no antioxidant) was hung in a 1 l sealed jars containing 10.0 g linoleic
acid stored in dark at 23 C and 40 C. The linoleic acid was periodically sampled and diluted with
cyclohexane, and the extent of oxidation in it was determined by quantifying conjugated dienes measured
optically at 234 nm using a spectrophotometer (UV-1700 UVVis spectrophotometer, Shimadzu Co.,
Kyoto, Japan). Molar concentrations of dienes were calculated using an absorption coefcient of
26 000 l/mol cm.19,20 The length of the induction period (time at which active oxidation commenced)
was used as an index to evaluate the antioxidant effect of sesamol lms.21,22

Antioxidant effect of sesamol and BHT lms on oat cereal


Flexible pouches (30  22 cm) were fabricated from lms B and C to investigate the effectiveness of
sesamol and compare the performance of sesamol with BHT. Each pouch was lled with 200 g of
cereal and then heat sealed with an impulse heat sealer (12AS, Sencorp System, Inc., Hyannis,
MA, USA). All pouches were stored in dark at 23 C. After 1 year, the extent of lipid oxidation was
determined using the solid phase micro-extraction (SPME) GC method modied from Brunton and
Okabe23,24 to estimate hexanal (a volatile secondary lipid oxidation product) concentrations in the
pouches. For hexanal extraction, cereal samples (1.0 g each) were placed in 20 ml headspace vials
(I-Chem, Chase Scientic Glass, Inc., Rockwood, TN, USA), tightly sealed and immersed in a water
bath (70 C). An SPME bre (Carboxen/PDMS, Sigma-Aldrich Co. Milwaukee, WI, USA) was
inserted into each vial for 5 min; the bre was then removed from the vial and inserted into the
injection port of a GC with a FID detector and HP-5 capillary column. Volatile compounds from
the cereal extracted by SPME were separated with temperature programming with an initial oven
temperature of 80 C (hold 1 min), increased to 180 C at a rate of 8 C/min (held 1 min) and increased
to 250 C (held 5 min). Carrier gas was nitrogen at a ow rate of 1 ml/min. Hexanal (99%) was used as
a retention time standard for identication, and 2-methyl-pentanal (98%) was added to each sample as
an internal quantication standard for normalization of FID detector response. The concentration of
hexanal (micromoles hexanal per kilogram cereal, mmole/kg) in the cereal was determined from a
standard curve of pure hexanal. Intensity and character of odours from cereal samples in different
packaging were also compared using an informal sensory panel consisting of approximately 10
students and professors in our laboratory.

Physical properties (thickness, tensile strength and transparency) of antioxidant lms


The average lm thickness was calculated from measurements at 10 random locations using a digital
micrometer (Digitrix, Fowler & NSK Co., Tokyo, Japan). Tensile properties including tensile strength,
Youngs modulus and toughness of the lms were determined using a TA-XT2i instrument and
Texture Expert Exceed software (Stable Microsystems, Godalming, Surrey, UK) according to ASTM
D 882-883.25 The lm specimens, 50  20 mm strips, were conditioned in an environmental chamber
at 52  2% relative humidity at 25 C for 1 week prior to testing. For each lm, ve specimens were
tested and averaged. Transparency was determined according to ASTM D 1746-70 by measuring
specular transmittance of the lms at 555 nm.26
Copyright 2012 John Wiley & Sons, Ltd.

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DOI: 10.1002/pts

ANTIOXIDANT EFFECT OF SESAMOL

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RESULTS AND DISCUSSION


Antioxidant retention in lms
As shown in Table 1, the sesamol lms (lms A and B) retained 1218 mg/kg and 646 mg/kg sesamol,
corresponding to 39% and 35% losses of sesamol, respectively. As a comparison, the BHT-containing
lm C retained 1606 mg/kg BHT, corresponding to 20% loss of BHT. The losses were probably
caused partly by the extrusion process during which some of the antioxidant was vaporized into air
when the extrudate exited the die and partly by the dry mixing process during which some of the
antioxidant was left in the mixer. Because the boiling points of sesamol and BHT (272 C and
265 C, respectively) are comparable, the higher loss of sesamol was somewhat unexpected.
Release of sesamol from lm into package headspace
Film A containing 1218 mg/kg sesamol was exposed to air inside enclosed jars to simulate the release
of sesamol from lm matrix to package headspace. As shown in Figure 4, sesamol vaporized from
polymer matrix rapidly, losing 60% of sesamol from the lm matrix within 6 h at 10 C and within
1 h at 30 C. These results demonstrate that migration of sesamol from packaging lms to package
headspace is fast and temperature dependent. They also imply that different lm structures may be
needed for foods stored at different temperatures and that shifts in temperatures during storage will
change rates at which sesamol is released from lms. This is probably advantageous because increases
in oxidation with temperature will be compensated by parallel increases in antioxidant release. Other
polymers should also be tested in the future to slow down the release of sesamol to obtain a better
control of its release kinetics for CRP application to meet the requirements of different food products.
Antioxidant effect of sesamol lm on linoleic acid
When incubated with linoleic acid in a closed system, released sesamol from lm A extended the
induction periods of linoleic acid from 1.3 days (control) to 10.6 days at 23 C and from 6.6 h (control)
to 35.1 h at 40 C (Figure 5). Thus, sesamol released from polymer lms extended the induction period
of linoleic acid oxidation by 529% and 793% relative to control lms at 40 C and 23 C, respectively.
Because there is no direct contact of lm with linoleic acid, sesamol must rst evaporate from the lm
into the headspace and then condense onto linoleic acid to inhibit its oxidation.
Lee et al.27 reported that a laminated pouch consisting of an HDPE layer and a heat seal layer
impregnated with BHT retarded linoleic acid oxidation, while lms containing 73 mg/kg a-tocopherol
failed to do so in a model of packaged solid food containing 0.36% (w/w) of linoleic acid in 1 kg food
at 45 C and 50% relative humidity. Wessling et al.8 also found that BHT was released from LDPE lm
and extended the shelf life of cereal food, while a-tocopherol was not released from LDPE lms and
thus was ineffective with dry products. These observations suggest that packaging lms containing
volatile antioxidants such as sesamol and BHT can provide distinct advantages for food products that
have little direct contact with packaging lms.

Figure 4. Release prole of sesamol; = sesamol release at 30 C and = sesamol release at 10 C.
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Concentration of conjugated dienes


(mol/l)

0.450

0.400
0.350
0.300
0.250
0.200
0.150
0.100
0.050
0.000
0

6
8
Time (days)

10

12

14

Concentration of conjugated dienes


(mol/l)

0.450

0.400
0.350
0.300
0.250
0.200
0.150
0.100
0.050
0.000
0

10

20

30
40
Time (hrs)

50

60

70

Figure 5. Effect of sesamol lm on formation of conjugated dienes in linoleic acid at 23 C (A) and
40 C (B); = control and = sesamol lm.
Antioxidant effect of sesamol and BHT lms on oat cereal
Figure 6 shows the hexanal concentrations in the cereal pouches estimated using the SPME method.
Although this method might not provide absolute values for hexanal concentrations, it is sufcient
to indicate the relative concentrations of hexanal among the samples for comparison purpose.
After 1 year of storage at 23 C in dark, cereal packed in different lms showed distinctly different
hexanal concentrations, an indicator of lipid oxidation.28 Hexanal levels were 85% lower in the BHT
pouches and 59% lower in the sesamol pouches than that in the control pouches (p < 0.05) (Figure 6).
Because the amount of sesamol was less than half the amount of BHT in the pouches, the antioxidant
effectiveness of BHT and sesamol pouches were comparable. The informal sensory evaluation
concluded that no off-odours were detected in the BHT or sesamol pouches, while strong rancid odour
was detected in the control pouches. This shows that even though the antioxidants volatilized from the

Figure 6. Hexanal concentration extracted by SPME in cereal packaged by different lms after 1 year
of storage.
Copyright 2012 John Wiley & Sons, Ltd.

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Table 2. Mechanical and optical properties of lms with and without antioxidants.
Controls (no antioxidant)
Film A

Film B/C

Sesamol and BHT


Film A

Film B

Film C

Film thickness (mm)


76.2 (2.5)
75.4 (1.5)
73.8 (2.9)
76.2 (2.5)
73.7 (2.5)
Tensile strength (MPa) 1.15E4 (1.17E3) 1.34E4 (737) 1.02E4 (295) 1.42E4 (387) 1.40E4 (524)
Youngs modulus (MPa) 4.99 (0.79)
7.41 (0.60)
4.22 (0.35)
7.94 (0.55)
7.83 (0.97)
Toughness (MPa)
59.3 (2.8)
67.1 (6.0)
54.0 (0.9)
70.4 (3.5)
69.0 (3.9)
Transparency (%)
76.3 (0.9)
38.3 (1.4)
76.3 (0.8)
40.9 (1.2)
36.9 (1.5)
In controls, lms A and B/C represent the control lms with the same polymer composition as lms A, B and C. Standard
deviations are reported in brackets.

packaging lms within hours, the effect continued for an extended period. The BHT and sesamol
samples were indistinguishable by taste and odour after 1 year, suggesting that sesamol may be an
effective alternative to BHT for stabilizing cereal products.
Physical properties
Table 2 shows that there are slight variations in thickness of the lms produced, which is common for
lm production. When these variations are taken into account, the data show that the addition of
sesamol or BHT has slight or no practical impact on the tensile and optical properties.

CONCLUSION
Sesamol could be successfully incorporated into packaging lms with at least 60% of the added amounts
retained in the lms after production. The release of sesamol from the lm was completed within 25 h at
10 C and 30 C. Despite the fast release, sesamol antioxidant action continued over extended periods for
both linoleic acid and cereal samples. After a year of storage, cereal samples packaged with sesamol lms
were substantially better than those packaged with controlled lms and were comparable with those
packaged with BHT lms in terms of lower hexanal concentration and rancid odours. The incorporation
of sesamol affected the tensile and optical properties of the lms only slightly.

ACKNOWLEDGEMENTS
This work was partly supported by National Research Initiative Grant 2006-35503-17568 from the USDA
Cooperative State Research, Education, and Extension Service Program on Improving Food Quality and Value,
as well as partly supported by a grant from the US Army Natick Research, Development, and Engineering
Laboratory through a grant to Berry Plastics. The authors thank Saikiran Chaluvadi and Vara Prasad Prodduk
for assistance in preparing this paper.

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