Midterms [Lipids] Flashcards
Lipids
- naturally-occuring fat-like substances
- generally insoluble in water
- can be synthesized in the liver
Fats and oils
esters of long chain carboxylic acid
Fats
- solid at room temperature
- derived from from animal sources
Fats
- solid at room temperature
- derived from from animal sources
Oils
- liquid
- plants
Fatty acids
- smaller units of lipids
- long chain carboxylic acids (COOH)
Saturated fatty acids
- single bonds only
Unsaturated fatty acids
- has double bonds
In writing fatty acid names
- based on carbon atoms
- based on the number of double bonds (Cx:y)
Monounsaturated
- one double bond
Polyunsaturated
- two or more double bonds
x-Omega fatty acid
- x = At what carbon the the double bond is found
Structure of lipids
- polymers of fatty acids
- typically made of a glycerol backbone, 2 fatty acid tails (hydrophobic), and a phosphate group (hydrophilic)
Simple lipids
- fats, oils, and waxes
Compound lipids
- phospholipids, glycolipids, lipoproteins
Derived lipids
- carotenoids, steroids, bile acids
Carotenoids
- precursor/source of vitamin A
Esterification
- reaction between a carboxylic acid and an alcohol to form ester and water
Free fatty acids
- they occur primarily esterified to glycerol
Waxes
- esters of fatty acids and alcohols
Cholesteryl palmitate containing cholesterol
- wax found in the blood plasma
Essential fatty acids
- body cannot produce and must be added into or obtained from the diet
Non-essential fatty acids
body can produce or synthesize
Phospholipids (phosphatides)
- names as the derivative of the parent compound
Emulsifier
- stands in between oil and water and holds/combines them together
- makes an emulsion stable
Functions of emulsifiers
- promote emulsion stability
- stabilize aerated systems like ice cream, mayonnaise
How does emulsifiers work
- they reduce surface tension between the two immiscible phases
Cephalin
- contain ethanolamine or serine in place of choline in lecithin
- prevalent in brain tissue
Sphingomyelins
- with a fatty acid in amide linkage on the amino group
- concentrated in brain and tissue
Glycolipids
- portion of molecule is formed by carbohydrates
Sterols-cholesterol
- a high molecular weight cyclic alcohol found in high amounts in egg yolk
Bile acids
- found in the bile combined by the way of their carboxylic groups with the amino acid glycine
Triglycerides
- ester derived from glycerol and three fatty acids
Biological functions of lipids
- chemical messengers
- storage and provision of energy
- maintenance of temperature
Functions of lipids in foods
- contribute to many desirable qualities of foods
- texture, structure, mouthfeel, flavor, and color
Rancidity
- water and oil creates bad smell
Hydrolytic rancidity
- involves moisture/water
- ester linkages of lipids are subject to hydrolysis by enzymes
Oxidative rancidity
- involves oxygen
- dominant in unsaturated fatty acids
Lipid deterioration
- lipolysis seriously degrades the quality of fat systems
Antioxidants
- retard the rate of oxidation
Function of antioxidants
- they direct the breakdown of peroxides into stable substances that do not promote further oxidation
Mechanism of antioxidants
- RO + AH -> RH (AH = antioxidants)
- ROO + AH -> ROOH + A
Synthetic antioxidants
- butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), propyl gallate (PG), and tert-butyl-hydroquinone (TBHQ)
Natural antioxidants
- ascorbic acid, tocopherols, carotene
Methods measuring lipid quality
- saponification value/number
- iodine value/number
- refractive value
- acid value
- peroxide value
Saponification
- product of soap using fat with a reaction of an alkali
Saponification value/number
- helps to know the amount of free fatty acids
- number of milligrams of potassium hydroxide (KOH) required to saponify one gram of fat under a specified condition
- know hydrolytic rancidity
Potassium laurate
- Alcohol + Alkaline = potassium salt
Steps in saponification
- Draw the structure to show the reaction
- Label each part of the reaction
- Calculate for molecular weight (H=1, C =12, O=16, K=39)
- Ratio and proportion
- Find how many g of KOH to saponify 1g of trilaurin
Iodine number
- number of grams of iodine that can saturate the double bonds of a fat or oil
- determine the amount of unsaturation in fats, oils, and waxes
More unsaturated
- more liquid (oil)
More saturated
- more solid (fat)
Calculations of iodine number
- Draw the structure
- Calculate the molecular weight
- Show the reaction
- Round off to the whole number
Acid number
- measure of the number of carboxylic acid groups in a chemical compound, such as fatty acid, or in a mixture of compounds
Refractive index
- a physical attribute of triglycerides
- indicated the possible chances of rancidity development in oil
- the higher the RI, the higher the chances of spoilage due to oxidation
Peroxide value
- the amount of peroxide oxygen per 1 kilogram of fat or oil
- indicator of deterioration of fats
- can be used to estimate oxidation of fats
Modification of lipids
- to improve their functional properties such as oxidative stability, flavor properties, nutrient content
Hydrogenation
- addition of hydrogen to split double bonds and produce single bonds
- unsaturated to saturated at 60C with catalyst
Reasons for hydrogenation
- provides a semi-solid fat at room temperature from an oil source
- increase oxidative stability during storage
- typical products that result include shortening and margarine
Interesterification
- involves rearranging the fatty acids in a triglyceride in such a way that they become distributed randomly among the triacylglycerol molecules of fat
- change the overall melting profile, spreadability, and solid-fat content temperature profile
Chemical Interesterification
- use sodium methoxide as a catalyst
- to shift the fatty acid of the triglycerides
- randomly darken the oils
Enzymatic Interesterification
- using lipases from bacterial, yeast, and fungal sources
- require less severe reaction conditions, easily purified products
- expensive
Application Interesterification
- modification of lard (pork fat)
- grainy texture, poor appearance, and poor creaming capacity
Fractionation
- change the physical properties and the nutritional value into a higher melting and a low melting or even liquid fraction
- done either by dry process
- means altering the proportion of solid to liquid
Application of Fractionation
- manufacturers of margarines and cooking fats because it can partly replace the incorporation of hydrogenated fats
- reduction of trans fats
Chemistry of frying
- exchange of water in food and oil
- results in distinctive fried flavors and undesirable off-flavors if the oil is overly deteriorated
Off-flavors in frying via
- hydrolysis
- oxidation
- polymerization reactions
Factors that control hydrolysis of triacylglycerols and glycerols
- oil temperature
- interface area between oil and aqueous phases
- water level
- steam level
Polymerization
- reaction takes place during frying
Degradation products..
- negatively affect not only flavor and safety but also color and texture of the fried products