: Edible oil is oxidized during processing and storage via autoxidation and photosensitized oxidation, in which triplet oxygen (3O2) and singlet oxygen (1O2) react with the oil, respectively. Autoxidation of oils requires radical forms of acylglycerols, whereas photosensitized oxidation does not require lipid radicals since 1O2 reacts directly with double bonds. Lipid hydroperoxides formed by 3O2 are conjugated dienes, whereas 1O2 produces both conjugated and nonconjugated dienes. The hydroperoxides are decomposed to produce off-flavor compounds and the oil quality decreases. Autoxidation of oil is accelerated by the presence of free fatty acids, mono- and diacylglycerols, metals such as iron, and thermally oxidized compounds. Chlorophylls and phenolic compounds decrease the autoxidation of oil in the dark, and carotenoids, tocopherols, and phospholipids demonstrate both antioxidant and prooxidant activity depending on the oil system. In photosensitized oxidation chlorophyll acts as a photosensitizer for the formation of 1O2; however, carotenoids and tocopherols decrease the oxidation through 1O2 quenching. Temperature, light, oxygen concentration, oil processing, and fatty acid composition also affect the oxidative stability of edible oil.

Mechanisms and Factors for Edible Oil Oxidation

Deep-fat frying produces desirable or undesirable flavor compounds and changes the flavor stability and quality of the oil by hydrolysis, oxidation, and polymerization. Tocopherols, essential amino acids, and fatty acids in foods are degraded during deep-fat frying. The reactions in deep-fat frying depend on factors such as replenishment of fresh oil, frying conditions, original quality of frying oil, food materials, type of fryer, antioxidants, and oxygen concentration. High frying temperature, the number of fryings, the contents of free fatty acids, polyvalent metals, and unsaturated fatty acids of oil decrease the oxidative stability and flavor quality of oil. Antioxidant decreases the frying oil oxidation, but the effectiveness of antioxidant decreases with high frying temperature. Lignan compounds in sesame oil are effective antioxidants in deep-fat frying.

https://onlinelibrary.wiley.com:443/doi/pdf/10.1111/j.1750-3841.2007.00352.x

Chemistry of deep-fat frying oils

Preface to the First Edition. Preface to the Second Edition. Contributors. List of Abbreviations. 1 Production and Trade of Vegetable Oils ( Frank D. Gunstone ). 1.1 Extraction, refining and processing. 1.2 Vegetable oils: Production, consumption and trade. 1.3 Some topical issues. 2 Palm Oil ( Siew Wai Lin ). 2.1 Introduction. 2.2 Composition and properties of palm oil and fractions. 2.3 Physical characteristics of palm oil products. 2.4 Minor components of palm oil products. 2.5 Food applications of palm oil products. 2.5.1 Cooking/frying oil. 2.6 Nutritional aspects of palm oil. 2.7 Sustainable palm oil. 2.8 Conclusions. 3 Soybean Oil ( Tong Wang ). 3.1 Introduction. 3.2 Composition of soybean and soybean oil. 3.3 Recovery and refining of soybean oil. 3.4 Oil composition modification by processing and biotechnology. 3.5 Physical properties of soybean oil. 3.6 Oxidation evaluation of soybean oil. 3.7 Nutritional properties of soybean oil. 3.8 Food uses of soybean oil. 4 Canola/Rapeseed Oil ( Roman Przybylski ). 4.1 Introduction. 4.2 Composition. 4.3 Physical and chemical properties. 4.4 Major food uses. 4.5 Conclusion and outlook. 5 Sunflower Oil ( Maria A. Grompone ). 5.1 Introduction. 5.2 Sunflower oil from different types of seed. 5.3 Physical and chemical properties. 5.4 Melting properties and thermal behaviour. 5.5 Extraction and processing of sunflower oil. 5.6 Modified properties of sunflower oil. 5.7 Oxidative stability of commercial sunflower oils. 5.8 Food uses of different sunflower oil types. 5.9 Frying use of commercial sunflower oil types. 6 The Lauric (Coconut and Palm Kernel) Oils ( Ibrahim Nuzul Amri ). 6.1 Introduction. 6.2 Coconut oil. 6.3 Palm kernel oil. 6.4 Processing. 6.5 Food uses. 6.6 Health aspects. 7 Cottonseed Oil ( Michael K. Dowd ). 7.1 Introduction. 7.2 History. 7.3 Seed composition. 7.4 Oil composition. 7.5 Chemical and physical properties of cottonseed oil. 7.6 Processing. 7.7 Cottonseed oil uses. 7.8 Co-product uses. 8 Groundnut (Peanut) Oil ( Lisa L. Dean, Jack P. Davis, and Timothy H. Sanders ). 8.1 Peanut production, history, and oil extraction. 8.2 Oil uses. 8.3 Composition of groundnut oil. 8.4 Chemical and physical characteristics of groundnut oil. 8.5 Health issues. 9 Olive Oil ( Dimitrios Boskou ). 9.1 Introduction. 9.2 Extraction of olive oil from olives. 9.3 Olive oil composition. 9.4 Effect of processing olives on the composition of virgin olive oils. 9.5 Refining and modification. 9.6 Hardening and interesterification. 9.7 Quality, genuineness and regulations. 9.8 Consumption and culinary applications. 10 Corn Oil ( Robert A. Moreau ). 10.1 Composition of corn oil. 10.2 Properties of corn oil. 10.3 Major food uses of corn oil. 10.4 Conclusions. 11 Minor and Speciality Oils ( S. Prakash Kochhar ). 11.1 Introduction. 11.2 Sesame seed oil. 11.3 Rice bran oil. 11.4 Flaxseed (linseed and linola) oil. 11.5 Safflower oil. 11.6 Argan kernel oil. 11.7 Avocado oil. 11.8 Camelina seed oil. 11.9 Grape seed oil. 11.10 Pumpkin seed oil. 11.11 Sea buckthorn oil. 11.12 Cocoa butter and CBE. 11.13 Oils containing a-linolenic acid (GLA) and stearidonic acid (SDA). 11.14 Tree nut oils. Useful Websites. Index.

http://health120years.com/cn/pdf/hd_Vegetable.Oils.pdf

Vegetable Oils in Food Technology: Composition, Properties, and Uses

Antioxidants delay or inhibit lipid oxidation at low concentration. Tocopherols, ascorbic acid, carotenoids, flavonoids, amino acids, phospholipids, and sterols are natural antioxidants in foods. Antioxidants inhibit the oxidation of foods by scavenging free radicals, chelating prooxidative metals, quenching singlet oxygen and photosensitizers, and inactivating lipoxygenase. Antioxidants show interactions, such as synergism (tocopherols and ascorbic acids), antagonism (α-tocopherol and caffeic acid), and simple addition. Synergism occurs when one antioxidant is regenerated by others, when one antioxidant protects another antioxidant by its sacrificial oxidation, and when 2 or more antioxidants show different antioxidant mechanisms.

Mechanisms of Antioxidants in the Oxidation of Foods

Lipid oxidation is important to food manufacturers especially when they increase unsaturated lipids in their products to improve nutritional profiles. Unfortunately, the number of antioxidants available to food manufacturers to control oxidative rancidity is limited and the approval of new antioxidants is unlikely due to economic barriers in obtaining government approval for new food additives. Therefore, new antioxidant technologies are needed for food oils. This paper reviews the current knowledge of lipid oxidation in foods with emphasis on how physical properties of food systems impact oxidation chemistry. In particular, the role of association colloids in bulk oils on lipid oxidation chemistry is discussed in an attempt to understand mechanisms of oxidation. Increasing the understanding of how physical properties impact lipid oxidation could lead to the development of novel antioxidant technologies that not only protect the oil against oxidation and increase shelf-life but also allow food manufacturers to include more nutritionally beneficial fatty acids in their products.

http://nfscfaculty.tamu.edu/talcott/courses/FSTC605/Papers%20Reviewed/Lipid%20Oxidation%20and%20Bulk%20oils.pdf

Role of Physical Structures in Bulk Oils on Lipid Oxidation

The processes of degumming, alkali refining, bleaching and deodorization removed 99.8% phospholipids, 90.7% iron, 100% chlorophyll, 97.3% free fatty acids and 31.8% tocopherols from crude soybean oil. The correlation coefficient between the removals of phosphorus and iron in soybean oil during processing was r = 0.99. The relative ratios of α-, β -, γ- and δ-tocopherols in crude oil, degummed oil, refined oil, bleached oil and deodorized soybean oil were almost constant, γ- and δ -tocopherols represented more than 94% of tocopherols in soybean oil. The order of oxidation stability of oil is crude > deodorized > degummed > refined > bleached oil.

Effects of processing steps on the contents of minor compounds and oxidation of soybean oil

Soybean oil purified by silicic acid column chromatography did not contain peroxides, free fatty acids, phospholipids or oxidized polar compounds. The purified soybean oil was thermally oxidized at 180°C for 96 hr in the presence of air. The thermally oxidized compounds (31.3%) were separated from the purified soybean oil by gradient elution silicic acid chromatography. Thermally oxidized compounds contained hydroxyl groups, carbonyl groups andtrans double bonds according to the infrared spectrum. Thermally oxidized compounds were added to soybean oil and purified soybean oil at 0, 0.5, 1.0, 1.5 and 2.0% to study the effects of these compounds on the oxidative stability of oil. The oxidative stabilities of oils were determined by gas chromatographic analysis of volatile compound formation and molecular oxygen disappearance in the headspace of oil bottles. The thermally oxidized compounds showed prooxidant effects on the oxidative stabilities of both refined, bleached and deodorized soybean oil and purified soybean oil. Duncan’s Multiple Range Test showed that thermally oxidized compounds had a significant effect on the volatile compound formatiion and oxygen disappearance in the headspace of oil at α=0.05.

S. H. Yoon

Papers

Effects of processing steps on the contents of minor compounds and oxidation of soybean oil

Effects of thermally oxidized triglycerides on the oxidative stability of soybean oil