Chemical Properties of Food Chapter

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Questions and Answers

What is the primary objective of hydrogenating liquid oils?

To convert them into a semi-solid fat suitable for use in spreads.

How does hydrogenation affect the content of polyunsaturated fatty acids?

It reduces the content of polyunsaturated fatty acids significantly.

What are the two key changes in physical properties resulting from hydrogenation?

An increase in melting point and an increase in oxidative stability.

What is formed during the hydrogenation of linoleate?

<p>A mixture of cis and trans 18:1 isomers, referred to as 'oleate'.</p> Signup and view all the answers

Why are partially hydrogenated vegetable oils a major source of trans acids?

<p>Because they contain a considerable proportion of trans 18:1 fatty acids formed during the hydrogenation process.</p> Signup and view all the answers

What health implications are associated with trans acids?

<p>They raise LDL levels and lower HDL levels in the body.</p> Signup and view all the answers

What alternatives to hydrogenation have been explored due to concerns over trans acids?

<p>Modifications of the hydrogenation process and interesterification of suitable blends.</p> Signup and view all the answers

What is the significance of labeling trans acids in some countries?

<p>It helps consumers make informed choices regarding their dietary intake of trans fats.</p> Signup and view all the answers

What complicates the inhibition of oxidation in foods and biological systems?

<p>The presence of emulsions of lipids and aqueous systems complicates oxidation inhibition.</p> Signup and view all the answers

Why is the detailed structure of hydroperoxides significant?

<p>It controls the chemical structure of volatile short-chain compounds, influencing flavor and odor.</p> Signup and view all the answers

What role do antioxidants play in the stability of oils and fats?

<p>Antioxidants protect oils and fats against autoxidation, thus enhancing their stability.</p> Signup and view all the answers

How do natural antioxidants differ from synthetic ones in food products?

<p>Natural antioxidants are often already present in oils, while synthetic antioxidants must be added to meet demand.</p> Signup and view all the answers

How do the oxidation rates of trienes compare to dienes?

<p>Trienes oxidize faster than dienes, producing volatile aldehydes with lower threshold values.</p> Signup and view all the answers

Why is total tocol content insufficient for measuring antioxidant activity?

<p>Different tocols have varying antioxidant activities, making total content alone an inadequate measure.</p> Signup and view all the answers

What happens to a fatty molecule during oxidation?

<p>One fragment remains attached to glycerol while the methyl end offers a volatile component.</p> Signup and view all the answers

What are the three stages of autoxidation?

<p>The three stages are initiation, propagation, and termination.</p> Signup and view all the answers

What can happen to antioxidants during the refining process of oils?

<p>Some natural antioxidants may be lost during refining, resulting in less stable refined oils.</p> Signup and view all the answers

What is the ratio of reaction rates between the autoxidation of oleate and linolenate?

<p>The ratio of reaction rates is 30,000 for oleate and 900 for linolenate.</p> Signup and view all the answers

Why is it important to manage the concentration of synthetic antioxidants in foods?

<p>Higher concentrations may cause tocopherols to act as pro-oxidants, undermining their protective role.</p> Signup and view all the answers

What should be considered regarding the distribution of antioxidants in emulsions?

<p>The distribution of antioxidants and pro-oxidants between oil and water phases is crucial for stability.</p> Signup and view all the answers

Why might some aldehydes remain in the oil after refining?

<p>Short-chain fragments attached to glycerol are likely to remain post-refining.</p> Signup and view all the answers

How can the reaction of hydroperoxides with metal ions be prevented?

<p>Keeping hydroperoxides and metal ions apart can be assisted by controlling pH and selecting appropriate emulsifiers.</p> Signup and view all the answers

What can be inferred about the relationship between oxygen species in oxidation?

<p>Triplet state oxygen is involved in autoxidation while singlet state oxygen is linked to photo-oxidation.</p> Signup and view all the answers

What are some sources of natural antioxidants found in plants?

<p>Natural antioxidants can be found in the leaves or seeds of certain plants.</p> Signup and view all the answers

What is the primary source of fats consumed in the US, and what type of fatty acid is predominant in it?

<p>Soybean oil is the primary source of fats, and it is rich in polyunsaturated fatty acids.</p> Signup and view all the answers

According to US legislation, what claim can be made about products with less than 0.5 g of non-conjugated trans acids per 14 g serving?

<p>These products may be labeled as containing zero trans fats.</p> Signup and view all the answers

What is 'hardstock' and how is it typically produced?

<p>'Hardstock' is produced through complete hydrogenation of unsaturated acids to convert them to saturated analogues.</p> Signup and view all the answers

What molecular changes can occur during the hydrogenation process?

<p>Changes include hydrogenation of unsaturated centers, stereomutation to higher-melting trans isomers, and double bond migration.</p> Signup and view all the answers

During the conversion of diene to monoene and to saturated acid/ester, what is the role of intermediate states such as DH and MH?

<p>Intermediate states DH and MH are formed during the half hydrogenated stages and are essential for the conversion process.</p> Signup and view all the answers

Which step is rate-determining in the conversion of D to M and why is it significant?

<p>The first step in the conversion of D to M is rate-determining, which results in low levels of DH.</p> Signup and view all the answers

What can happen to the levels of DH if hydrogen is present in very low concentration?

<p>The levels of DH will be low, and the conversion of DH back to D will be slow.</p> Signup and view all the answers

What is the typical iodine value (IV) of hardstock and what does this indicate?

<p>The typical iodine value of hardstock is around 2, indicating very low levels of unsaturated fatty acids.</p> Signup and view all the answers

What is the primary vitamin E form found in soybean oil?

<p>The primary vitamin E form found in soybean oil is $γ$-tocopherol.</p> Signup and view all the answers

Can you identify the oil with the highest total vitamin E content?

<p>Wheat germ oil has the highest total vitamin E content at 254 mg/100 g.</p> Signup and view all the answers

Which oil contains tocotrienols in addition to tocopherols?

<p>Palm oil contains both tocopherols and tocotrienols.</p> Signup and view all the answers

What distinguishes sesame oil from others mentioned in the content?

<p>Sesame oil is distinguished by its content of compounds such as sesamin, sesamolin, and sesaminol.</p> Signup and view all the answers

Which vegetable oil has the lowest vitamin E content according to the information provided?

<p>Butter has the lowest vitamin E content with only 2 mg/100 g.</p> Signup and view all the answers

What undesirable changes can occur to unsaturated fatty acids when heated above 180ºC?

<p>Cyclisation, geometrical isomerism, and polymerisation can occur.</p> Signup and view all the answers

How does the vitamin E content of olive oil compare to that of corn oil?

<p>Olive oil contains 22 mg/100 g of vitamin E, while corn oil contains 78 mg/100 g.</p> Signup and view all the answers

What is the total vitamin E content calculated in international units (IU) used for?

<p>The total vitamin E content calculated in IU accounts for the effect of each tocol on vitamin E activity.</p> Signup and view all the answers

How does the stereoisomerism of linolenic acid compare to that of linoleate at elevated temperatures?

<p>Linolenic acid undergoes stereoisomerism quicker than linoleate at temperatures above 220ºC.</p> Signup and view all the answers

What is the tocopherol content in cottonseed oil?

<p>Cottonseed oil has a tocopherol content of 78 mg/100 g.</p> Signup and view all the answers

What happens during the hydrolysis of glycerol esters?

<p>Glycerol esters are broken down into fatty acids and glycerol.</p> Signup and view all the answers

What is lipolysis and how does it relate to hydrolysis?

<p>Lipolysis refers to the hydrolysis of fats by lipases, splitting glycerol esters into fatty acids and glycerol.</p> Signup and view all the answers

Why are polyunsaturated fatty acids with an all-cis pattern important nutritionally?

<p>Their all-cis pattern is essential for maintaining their nutritional value.</p> Signup and view all the answers

What are the implications of polymerisation of polyunsaturated fatty acids during heating?

<p>Polymerisation results in the formation of dimers, trimers, and oligomers with increased molecular weight.</p> Signup and view all the answers

What analytical methods might be necessary to detect changes in heated polyunsaturated fatty acids?

<p>Special analytical methods tailored to identify specific changes like isomerism and polymerisation may be needed.</p> Signup and view all the answers

At what temperature is the risk of oxidative changes in polyunsaturated fatty acids heightened?

<p>The risk increases significantly at temperatures exceeding 180ºC.</p> Signup and view all the answers

Flashcards

Hydrogenation of Oils

A process that converts liquid oils into semi-solid fats, used to create spreads.

Trans Fatty Acids

A type of unsaturated fatty acid with a specific structure. They are more stable and increase the melting point of fats.

Spreadability

The ability of a fat to spread easily at room temperature.

Interesterification

The process of changing the arrangement of fatty acids within a fat molecule.

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Oxidation of Fats

The process of breaking down fats into simpler molecules, leading to rancidity.

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Saturated Fats

A type of fat that is solid at room temperature, often found in animal products.

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Unsaturated Fats

A type of fat that is liquid at room temperature, often found in plant products.

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Essential Fatty Acids

Fats that are essential for our bodies but cannot be produced by our bodies, and must be obtained from diet.

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Hydrogenation

The process of converting a liquid oil into a solid fat by adding hydrogen atoms to its unsaturated fatty acids.

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Cis Fatty Acid

A type of unsaturated fatty acid with a hydrogen atom on the same side of the double bond. These are typically found in natural fats and oils.

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Hydrolysis

The process of breaking down a complex fat (triglyceride) into simpler molecules (glycerol and fatty acids) by adding water molecules.

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Iodine Value (IV)

A measure of the degree of unsaturation in a fat or oil. It is determined by the amount of iodine that can be absorbed by the fat.

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Complete Hydrogenation

The conversion of unsaturated fatty acids into saturated fatty acids by adding hydrogen atoms, which eliminates double bonds. This process can also create trans fats.

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Trans Fat

A type of fat that is created during the hydrogenation process. Trans fats are considered unhealthy and can increase the risk of heart disease.

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Antioxidants

Substances that protect oils and fats from oxidation, which can make them rancid.

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Autoxidation

The process of oxygen reacting with fats or oils, leading to rancidity.

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Tocols

A group of natural compounds found in oils that act as antioxidants.

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Pro-oxidants

Compounds that can speed up oxidation in certain situations, potentially counteracting the effects of antioxidants.

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Induction period

The period during which an oil is stable and doesn't readily oxidize.

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Quencher molecules

Compounds that can inhibit or slow down the oxidation process.

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Refining

The process of removing impurities from oils, which can sometimes reduce their natural antioxidant content.

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Distribution of antioxidants

The distribution of antioxidants and pro-oxidants between the oil and water phases in an emulsion.

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Hydroperoxides in Oxidation

Hydroperoxides are formed when unsaturated fatty acids, like oleate, linoleate, and linolenic acid, undergo oxidation. The specific structure of these hydroperoxides influences the formation of volatile short-chain compounds, each having its own unique flavor and odor.

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Linolenic Ester Oxidation

Linolenic esters, which contain three double bonds (trienes), oxidize faster than dienes (two double bonds). The volatile aldehydes produced from linolenic acid have lower odor thresholds, meaning they are more noticeable at lower concentrations.

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Oxidation and Volatile Compounds

The oxidation of fatty molecules can lead to the formation of volatile compounds. One fragment, called the core aldehyde, remains attached to glycerol. The other fragment, at the methyl end of the molecule, is released as a volatile component. This volatile component can often cause undesirable flavors and aromas in oils.

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Refining and Core Aldehyde

In the oxidation process, the volatile component of a broken fatty molecule can be removed during refining. However, the core aldehyde that remains attached to glycerol will likely persist in the oil.

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Autoxidation Process

Autoxidation is a radical chain process that involves three stages: initiation, propagation, and termination. In initiation, free radicals are formed. During propagation, these radicals react with molecules, leading to the formation of more radicals. Termination occurs when two radicals combine to form a stable molecule.

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Oxidation Rates

The rate of autoxidation and photo-oxidation varies depending on the type of fatty acid. Linolenate oxidizes much faster than linoleate and oleate, indicating a higher susceptibility to oxidation.

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Oxygen and Oxidation Rate

During autoxidation, the presence of oxygen is crucial. Autoxidation rates are significantly higher in the presence of oxygen. Additionally, the type of oxygen, triplet or singlet, also influences the rate of oxidation.

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Photo-oxidation vs. Autoxidation

The ratio of reaction rates between photo-oxidation and autoxidation highlights the sensitivity of different fatty acids to light and oxygen. Linolenate is significantly more susceptible to photo-oxidation compared to oleate and linoleate, indicating a strong sensitivity to light.

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Alpha-tocopherol (␣-tocopherol)

The most abundant form of vitamin E found naturally in foods - it has the highest biological activity compared to other forms of vitamin E.

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Tocotrienols

A class of vitamin E molecules that contribute to its antioxidant properties; they have different structures and biological activities compared to tocopherols.

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International Units (IU) of vitamin E

The total amount of vitamin E in a food or supplement, calculated according to the biological activity of each different form of vitamin E.

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Gamma-tocopherol (␥-tocopherol)

A specific type of vitamin E that has been extensively studied for its potential health benefits, especially in promoting heart health.

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Avenanthramides

An antioxidant found in oats, known for its potential benefits in reducing inflammation and cholesterol levels.

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Sesaminol

A compound found in sesame seeds and oil, known for its potential to lower blood pressure and cholesterol.

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Oryzanols

A group of compounds found in rice bran oil, known for their antioxidant and potentially anti-inflammatory properties.

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Avenasterols

A group of compounds found in oats, known for their potential to reduce inflammation and improve blood sugar control.

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Hydrolysis of Fats

The process of breaking down fats into simpler molecules by adding water, often resulting in fatty acids and glycerol.

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Deodorization of Oils

The process of removing undesirable substances from fats and oils, such as free fatty acids, by using steam under pressure.

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Thermal Degradation of Fats

The breakdown of fats into smaller molecules, often triggered by heat or oxidation, leading to changes in the chemical composition of the fat.

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Geometric Isomerism of Fats

The process of changing the shape or arrangement of fatty acids, often resulting in the formation of cyclic structures or trans isomers, influencing the properties of the fat.

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Study Notes

Chemical Properties of Food

  • This chapter covers significant chemical reactions in the food industry, including hydrogenation, oxidation, thermal changes in double bond systems, and acid/ester reactions.

Hydrogenation

  • Hydrogenation is a reaction between unsaturated centers in oils/fats in the presence of a metallic catalyst.
  • This is a heterogeneous reaction (solid, liquid, and gas) occurring on a solid catalyst surface at specific temperature and pressure.
  • Hydrogenation changes physical, chemical, and nutritional properties of the products.
  • Millions of tonnes of soybean and other unsaturated vegetable oils (oleic, linoleic, linolenic acids) and fish oils are hydrogenated annually.
  • This process is practiced in three ways:
    • Brush hydrogenation: A short reaction to reduce linolenic esters in soybean and rapeseed/canola oils, increasing shelf life. This results in minimal trans isomer formation.
  • Partial hydrogenation: A significant method to process oils and fats converting a liquid oil into a semi-solid fat (e.g., spreads). It reduces polyunsaturated fatty acids and may form trans 18:1.

Atmospheric Oxidation

  • Unsaturated fats can react with oxygen (air), leading to rancidity.
  • This process occurs in two forms:
    • Autoxidation: A reaction with oxygen in the absence of light.
    • Photo-oxidation: A reaction with oxygen in the presence of light.
  • Oxidation leads to various products including hydroperoxides, short-chain molecules (e.g. aldehydes), and other compounds affecting odor, flavor, and stability.
  • The presence of antioxidants, copper, iron, and heat can impact the oxidation process.
  • The rate of oxidation is affected by the level and nature of unsaturation in the fats.

Thermal Changes

  • Elevated temperatures (>180°C) can cause undesirable changes in unsaturated fats, particularly those with multiple double bonds (e.g., linolenic acid, EPA, DHA).
  • Thermal changes involve:
    • Cyclization.
    • Geometrical isomerism (cis-trans).
    • Polymerization.
  • These changes are undesirable nutritionally as they can modify the structure of the polyunsaturated fatty acids.

Reactions of Carboxyl/Ester Functions

  • Oils and fats (glycerol esters) are reactive and can be modified through various processes:
    • Hydrolysis: The splitting of esters using water, producing fatty acids and glycerol. This can be catalyzed by acids, bases, or enzymes (lipases).
    • Alcoholysis: The reaction of esters with an alcohol, producing other esters.
    • Acidolysis: The reaction of esters with an acid, producing other esters.
    • Interesterification: The interchange of acyl groups between different ester molecules. This can be used to change the properties of oils & fats.

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