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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 inde nitely in a series of hydrogen abstraction that can potentially involve hundreds of lipid molecules from a 1 single initiation. 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 2 3 5 value and even generate toxic compounds, all of which shorten the shelf life of food products. To inhibit lipid oxidation, antioxidants are traditionally added into food formulation to quench lipid 4 free radicals, stop chain reactions and extend shelf life. An innovative technology for adding an antioxidant into food using the package as a delivery system is 5 known as controlled release packaging (CRP) in which the antioxidant is incorporated into the package and then released onto the food surface, where most lipid oxidation occurs, in continually replenished 6 small amounts to retard lipid oxidation. 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.

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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 7,8 packages of dry foods such as breakfast cereal. However, the current trend is to replace BHT and other potentially toxic synthetic additives with natural compounds, as the society prefers natural 8 products and greener labels. 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 9 and a phenolic group responsible for antioxidant activity. Sesamol has been shown to be a highly 10 11 effective antioxidant for inhibiting oxidation in lard and food oils and for stabilizing oils against 12 13 thermal degradation during frying and microwave heating. It has been shown that 100 mg/kg sesamol 14 and tocopherol reduced lipid oxidation and irradiation-induced off- avours in ground beef and 200 mM 15 sesamol stabilized irradiated pork homogenates and patties. 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 Scienti c Inc. (Suwanee, GA, USA). A commercial oat-based cereal was supplied by a major food company, not named for con dentiality 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

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

Antioxidant
Sesamol Sesamol BHT

Initial loading (mg/kg)


2000 1000 2000

Extractable antioxidant (mg/kg)


1218 11 646 18 1606 29

Film structure (layers)


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

Film A LLDPE HDPE+sesamol HDPE

Film B HDPE HDPE+sesamol EVA

Film C HDPE HDPE+BHT 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 16 chloride using the method of Obinata. 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 Scienti c Inc., New Brunswick, NJ, USA). Sesamol and BHT concentrations in the solvent were quanti ed 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. Packag. Technol. Sci. 2013; 26: 3138 DOI: 10.1002/pts

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incubated in an environmental chamber (C25KC, New Brunswick Scienti c 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) 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 UV Vis spectrophotometer, Shimadzu Co., Kyoto, Japan). Molar concentrations of dienes were calculated using an absorption coef cient of 19,20 26 000 l/mol cm. The length of the induction period (time at which active oxidation commenced) 21,22 was used as an index to evaluate the antioxidant effect of sesamol lms. 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 modi ed from Brunton and 23,24 Okabe 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 Scienti c 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 identi cation, and 2-methyl-pentanal (98%) was added to each sample as an internal quanti cation 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, Young s 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 25 D 882-883. 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 26 specular transmittance of the lms at 555 nm.
Copyright 2012 John Wiley & Sons, Ltd. Packag. Technol. Sci. 2013; 26: 3138 DOI: 10.1002/pts
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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. 27 Lee et al. 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 8 at 45 C and 50% relative humidity. Wessling et al. 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 pro le of sesamol; = sesamol release at 30 C and = sesamol release at 10 C.


Copyright 2012 John Wiley & Sons, Ltd. Packag. Technol. Sci. 2013; 26: 3138 DOI: 10.1002/pts

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0.450 Concentrationofconjugateddienes (mol/l) 0.400 0.350 0.300 0.250 0.200 0.150 0.100 0.050 0.000 0 2

X. ZHU ET AL.

68 10 Time (days)

12

14

0.450 Concentrationofconjugateddienes (mol/l) 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 suf cient 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 28 hexanal concentrations, an indicator of lipid oxidation. 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. Packag. Technol. Sci. 2013; 26: 3138 DOI: 10.1002/pts

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Table 2. Mechanical and optical properties of lms with and without antioxidants. Controls (no antioxidant) Film A Film B/C Film A Sesamol and BHT 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) Young s 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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Packag. Technol. Sci. 2013; 26: 3138 DOI: 10.1002/pts