Midterm Review Flashcards
What is the difference in terms of structure between liquid and solid waxes? Give examples of both.
Liquid wax: short-chain (ex: jojoba oil)
Solid wax: long-chain
In phospholipids, what is the structure called when X=OH?
Phosphatidic acid
In phospholipids, what is the structure called when X=O-CH2-CH2-NH2?
Phosphatidylethanolamine
In phospholipids, what is the structure called when X=O-CH2-CH2-N+(CH2)3
Phosphatidylcholine
In phospholipids, what is the structure called when X=O-CH2-CH(NH2)-COOH
Phosphatidylserine
In phospholipids, what is the structure called when X=sugar
Phosphatidylinositol
What are the three classes of phospholipids?
- Lecithins (Phosphatidylcholines)
- Cephalins (Phosphatidylethanolamines)
- Phosphatidyl inositols
How do short-chain fatty acids and long-chain fatty acids differ in terms of their contributions to flavour?
Short-chain FA: contribute to flavour
Long-chain FA: have no flavour per se BUT they will give a soapy flavour in the presence of salts
The presence of ________ can lower the smoke point of edible oils when used for frying.
free fatty acids
What does this structure correspond to?
CH3-(CH2)n-CH2-OH
How many carbons do they need to have at least?
- Alcohols
- At least 6 carbons
Short-chain ______ are often major contributors to flavour.
alcohols
How many carbons does a fundamental isoprene unit contain?
5 carbons
What are terpenes components of?
Components of the fragrant oils obtained from leaves, flowers and fruits
What are the main constituents of essential oils?
Monoterpenes, with sesquiterpenes
How many isoprene units and carbons do these terpene classes contain: A) Monoterpenes B) Sesquiterpenes C) Diterpenes D) Sesterterpenes E) Triterpenes
A) 2, 10 B) 3, 15 C) 4, 20 D) 5, 25 E) 6, 30
What is the main mechanism for oils becoming plastic fats?
cis -> trans conversion during hydrogenation
Differentiate unconjugated and conjugated double bonds.
Unconjugated: separated by methylene group (natural state of most fatty acids)
Conjugated: double bonds are next to each other, not interrupted by a methylene (CH2) group (not naturally found)
What does a mixed bonding system lead to? Where is that positioned?
- Leads to formation of an ACTIVE METHYLENE group
- Positioned between a conjugated and unconjugated double bonds
The omega nomenclature is based on two assumptions. What are they?
- All natural fatty acids are in the cis form
- The double bonds will be always be UNCONJUGATED
Arachidonic acid, C__, with __ unconjugated double bonds, the first double bond in position _, the next at _, _, and _, respectively
- C20
- 4 unconjugated double bonds
- 6, 9, 12, 15
What group does Erucic acid belong to?
Omega-9
What group does arachidonic acid belong to?
Omega-6
There are no simple, analytical methods for separating, isolating and identifying individual _________.
triglycerides
In plant seeds, what kind of lipids are used as a source of energy for germination?
Triglycerides
What lipid is responsible in part for the desirable flavour of aged cheese?
Short-chain fatty acids
How many carbons does the lauric acid group contain?
12
What are the sources of the lauric acid group?
- Oil palm (tropical oils)
- Palm kernal oil, coconut and babasu
How does palm kernal oil differ from palm oil?
- Palm kernal oil (extracted from palm oilseeds)
- Palm oil (from palm fruit), which is much more highly unsaturated and is not part of the lauric acid group
Are lauric acids solid or liquid at room temperature?
- Although largely saturated
- They are oils owing to the high proportion of C12 fatty acids in their triglycerides
What kind of fatty acids are resistant to oxidative rancidity? Which group is an example of this?
- Low degree of unsaturation
- Lauric acid
Most oils in this group tend to be categorized as industrial “drying oils”. Which group does this passage refer to?
Linolenic acid
Why are linolenic acids sometimes referred as “drying oils”?
Because of their ability to polymerize into a hard film if applied as a thin layer on surfaces (paint)
The polymerization capability is present in all _____________ oils, but those containing high levels of _____________ are more reactive
unsaturated oils, linolenic acid
What are common examples of the linolenic acid group?
Soybean, linseed, castor, hempseed and perilla oils
Processed soybean oil, if stored after extraction without modification, suffers from a problem commonly termed _______.
Reversion
What is reversion?
Relatively rapid transition from a bland, tasteless oil shortly after processing to a grassy, hay-like and then fishy flavour
How is reversion overcome? What fats are converted to what?
By hydrogenation to convert a substantial portion of linolenic to oleic and linoleic acids
Animal fat depot group has a higher ratio of what compared to the oleic-linoleic acid group?
Di-saturated (gs2u) and tri-saturated (gs3) glycerides
Some fish oil fatty acids can be highly unsaturated. Up to how many double bonds do they contain?
Up to 6 double bonds
What are two examples of the erucic acid group?
Rapeseed oil and mustard oil
How was rapeseed oil used originally?
Used extensively as a marine motor oil
What allows the separation of cis from trans isomers?
Silver ion chromatography
What kind of lipid is biodiesel?
Methyl esters
Which fatty acid group is useful in cosmetics?
Lauric acids
What is the fatty acid breakdown of olive oil?
- Oleic (75%) - M
- Palmitic (10%) - S
- Linoleic (10%) - U
What is the first step of the processing of oilseeds?
- Crush the oilseed
- Give the crush a heat treatment
What does the heat treatment of a crush do?
Aids in knocking out the enzymes lipase and lipoxygenase, which can cause a deteriorative reaction
What deteriorative reactions do lipases cause? How? What are they present in?
- Lipolysis
- Hydrolysis of the ester linkage between glycerol and a fatty acid in the TG
- Enzyme present in every living system
What deteriorative reactions do lipoxygenase cause? How?
- Autoxidation
- Oxidation of polyunsaturated fatty acid chains that have a cis,cis-1,4-pentadiene group (e.g. linoleic and linolenic)
In the case of fats and oils from animal and fish sources, what is the most common method of processing?
Rendering
What are the four steps most oils go through following extraction?
1) Settling/degumming
2) Refining
3) Bleaching
4) Deodorizing
What is the use of settling/degumming? What does it get rid of?
- Carbs, proteins and phospholipids hydrate and associate themselves with the aqueous phase
- Over time, aqueous phase separates from the oil, carrying with it the cellular debris, carbs and phospholipids
In the settling/degumming phase of soybean oil, what is recovered from the aqueous layer? Why?
- The phospholipids since soybeans contain 5-8% phospholipids (mainly lecithin)
- They have commercial value as emulsifiers
What does refining remove?
Removes the free fatty acids from the oil
What does bleaching remove?
Designed to remove the coloured material from the oil (carotenoids, chlorophyll, and pheophytin)
What does deodorization remove?
Removes the volatile compounds that give the oil off-flavours
In olive oil, what compounds are not removed for the best quality? Which steps are not used?
- Flavour and colour compounds
- Only pressed; bleaching and deodorization are not used
Define selectivity. It is a property of what?
- Preferentially hydrogenating more highly unsaturated fatty acids
- Property of the catalyst
What is proprietary?
Knowledge of conditions and selectivity characteristics provides control
What causes lard to be “grainy”?
In lard, the GS2U component is largely made up of oleopalmitostearin, which has a propensity to form large crystals.
How can the structure of lipids in human milk be reproduced artificially?
Enzymatic interesterification reaction using sn-1,3 specific lipase as a catalyst.
Why can fat have plasticity or spreadability?
Because a fat is made up of a liquid in a crystalline matrix
The crystalline matrix of fat forms a 3-D network that holds the system together by what force? How does it explain plasticity?
- Van der Waals forces
- Because they are weak forces, they can be broken and readily re-formed again
When a fat can be deformed readily, it is said to be in what range?
Plastic range
How is the solid fat content commonly determined?
- Dilatometry
- Nuclear magnetic resonance (NMR) measurements
What is plotted in dilatometry?
The specific volume is plotted as a function of temperature
What do the 3 curves in the specific volume over temperature graph represent?
A) Thermal expansion of the solid fat
B) Expansion due to a change in state
C) Thermal expansion of the liquid only
How does the pulsed NMR SFC measurement work?
- Sample of fat is placed in a magnetic field
- Radiofrequency (RF) pulse is applied perpendicular to the field to “tip” the spins
What is the signal accompanying the relaxation process of the 1H magnetic spins after they are disturbed by the RF pulse?
FID (free induction decay)
Which spins of the 1H nucleic relax more rapidly? Compared to what?
Spins in the solid state relax more rapidly than those in the liquid phase
What is polymorphism? What exhibits it?
- The occurrence of several different crystal forms for a single compound
- Triglycerides