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Rancidification
Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.
When these processes occur in food, undesirable odors and flavors can result. In processed meats these flavors are collectively known as warmed-over flavor. In certain cases the flavors can be desirable, as in aged cheeses.
Rancidification can detract from the nutritional value of food, as some vitamins are sensitive to oxidation. Oxidative degradation also occurs in other hydrocarbons, including lubricating oils, fuels, and mechanical cutting fluids.
Five pathways for rancidification are recognized:
Hydrolytic rancidity refers to the odor that develops when triglycerides are hydrolyzed and free fatty acids are released. This reaction of lipid with water may require a catalyst (such as a lipase, or acidic or alkaline conditions) leading to the formation of free fatty acids and glycerol. In particular, short-chain fatty acids, such as butyric acid, are malodorous. When short-chain fatty acids are produced, they serve as catalysts themselves, further accelerating the reaction, a form of autocatalysis.
Oxidative rancidity is associated with the degradation by oxygen in the air.
The double bonds of an unsaturated fatty acid can be cleaved by free-radical reactions involving molecular oxygen. This reaction causes the release of malodorous and highly volatile aldehydes and ketones. Because of the nature of free-radical reactions, the reaction is catalyzed by sunlight. Oxidation primarily occurs with unsaturated fats. For example, even though meat is held under refrigeration or in a frozen state, the poly-unsaturated fat will continue to oxidize and slowly become rancid. The fat oxidation process, potentially resulting in rancidity, begins immediately after the animal is slaughtered and the muscle, intra-muscular, inter-muscular and surface fat becomes exposed to oxygen of the air. This chemical process continues during frozen storage, though more slowly at lower temperature. Oxidative rancidity can be prevented by light-proof packaging, oxygen-free atmosphere (air-tight containers) and by the addition of antioxidants.
A double bond of an unsaturated fatty acid can be oxidised by oxygen from the air in reactions catalysed by plant or animal lipoxygenase enzymes, producing a hydroperoxide as a reactive intermediate, as in free-radical peroxidation. The final products depend on conditions: the lipoxygenase article shows that if a hydroperoxide lyase enzyme is present, it can cleave the hydroperoxide to yield short-chain fatty acids and dicarboxylic acids (several of which were first discovered in rancid fats).
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Rancidification
Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.
When these processes occur in food, undesirable odors and flavors can result. In processed meats these flavors are collectively known as warmed-over flavor. In certain cases the flavors can be desirable, as in aged cheeses.
Rancidification can detract from the nutritional value of food, as some vitamins are sensitive to oxidation. Oxidative degradation also occurs in other hydrocarbons, including lubricating oils, fuels, and mechanical cutting fluids.
Five pathways for rancidification are recognized:
Hydrolytic rancidity refers to the odor that develops when triglycerides are hydrolyzed and free fatty acids are released. This reaction of lipid with water may require a catalyst (such as a lipase, or acidic or alkaline conditions) leading to the formation of free fatty acids and glycerol. In particular, short-chain fatty acids, such as butyric acid, are malodorous. When short-chain fatty acids are produced, they serve as catalysts themselves, further accelerating the reaction, a form of autocatalysis.
Oxidative rancidity is associated with the degradation by oxygen in the air.
The double bonds of an unsaturated fatty acid can be cleaved by free-radical reactions involving molecular oxygen. This reaction causes the release of malodorous and highly volatile aldehydes and ketones. Because of the nature of free-radical reactions, the reaction is catalyzed by sunlight. Oxidation primarily occurs with unsaturated fats. For example, even though meat is held under refrigeration or in a frozen state, the poly-unsaturated fat will continue to oxidize and slowly become rancid. The fat oxidation process, potentially resulting in rancidity, begins immediately after the animal is slaughtered and the muscle, intra-muscular, inter-muscular and surface fat becomes exposed to oxygen of the air. This chemical process continues during frozen storage, though more slowly at lower temperature. Oxidative rancidity can be prevented by light-proof packaging, oxygen-free atmosphere (air-tight containers) and by the addition of antioxidants.
A double bond of an unsaturated fatty acid can be oxidised by oxygen from the air in reactions catalysed by plant or animal lipoxygenase enzymes, producing a hydroperoxide as a reactive intermediate, as in free-radical peroxidation. The final products depend on conditions: the lipoxygenase article shows that if a hydroperoxide lyase enzyme is present, it can cleave the hydroperoxide to yield short-chain fatty acids and dicarboxylic acids (several of which were first discovered in rancid fats).