Lipids Flashcards
Are lipids are homogeneous group or heterogeneous?
Heterogeneous group
What common properties do lipids share?
- Insolubility in aqueous or water based solutions
2. Solubility in organic or non-polar solvents
What is one of the best organic solvents?
Chloroform
How does the solubility of short-chained fatty acids compare to long-chained fatty acids? Why?
- Solubility decreases as the length of the carbon chain increases
- Charge distribution is relatively stronger
Which fatty acids are infinitely soluble in water?
Acetic acid (2C) Butanoic acid (4C)
Which fatty acids are soluble in chloroform (organic solvent)? How does the solubility chain with increase in size? Why?
- 10 C are ++ soluble (normal saturated fatty acids)
- Increase size, decrease solubility
- Long hydroC chain = Van der Waals interaction, will keep molecules together
What are normal saturated fatty less soluble in?
Acetonitrile
Name the 5 biological functions of lipids.
1) Storage of energy
2) Membrane structure
3) Signaling molecules
4) Cofactors for enzymes
5) Antioxidants
6) Pigments
Why are lipids good molecules for storage of energy?
Reduced compounds: lots of available energy
Hydrophobic nature: good packing, Why?
How do lipids act as signaling molecules?
Hormones (steroids)
Vitamins A and D (hormone precursors)
What colour is canthaxanthin? Zeaxanthin?
Canthaxanthin = bright red Zeaxanthin = bright yellow
What is the major difference between complex lipids and biologically active lipids?
Complex lipids: fatty acids
Biologically active lipids: no fatty acid
What is special about prostaglandins?
Derived from FA, do NOT contain FA
What are the two main groups of complex lipids, how do they differ?
Storage Lipids: non-polar
Structural Lipids: polar lipids
Name 2 storage lipids.
Triglycerides and Waxes
Name 2 structural lipids.
Phospholipids and sphingolipids
Name 2 biologically active lipids.
Prostaglandins and steroids
What kind of molecules are fatty acids? What are their chains composed of?
- Amphipathic molecules
- Hydrocarbon chains
- 3 to 35 carbons and a carboxylic acid group
Are lipids even or uneven in number? How?
- Even in number
- Nb of carbons + carboxylic group = makes it even
How can fatty acids be written in terms of structure?
CH3-(R)n-COOH , where R= CH2
n = or > 2.
What is the most common fatty acid chain length?
C14 to C18
Which fatty acid is infinitely soluble in water? How does solubility change with increased hydrocarbon chain?
- Butanoic acid (4C)
- Solubility decreases
Where is butanoic acid found in?
High concentration in breast milk -> promotes development of stem cells + metaboism
Is Lauric acid soluble in water? What is its main function?
- Partially soluble in water to the extent of 0.06 per gram of water
- Antimicrobial (soaps)
What kind of fatty acids form waxy solids at room temperature?
Fatty acids with C10 or higher saturated hydrocarbon chains
What kind of fatty acids form oily liquids at room temperature?
Fatty acids with C9 or lower saturated or unsaturated hydrocarbon chains
What is the difference between the systematic and common names of fatty acids?
- Systematic: chemist
- Common: based on the source
Are most natural fatty acids branched or unbranched? What is the prefix?
- Unbranched
- Prefix: n indicates normal or unbranched
What is the pKa of COOH group? At pH 7, how are the fatty acids?
- Below 5
- Fully ionized
What are saturated double bonds? Unsaturated?
Saturated: no double bonds
Unsaturated: one or more double bonds
What do cis-double bonds affect in terms of positioning?
- The positions of fatty acids tails relative to the plan of saturated lipid tails of the same length
- Produce more kinks or bents
Which are more packed: saturated fatty acids or unsaturated?
Saturated fatty acids are more packed
What does less ordered packing lead to?
- Weaker intermolecular interactions (Van der Waal)
- Lower melting point for unsaturated fatty acids
What does configuration mean? Conformation? What is cis/trans?
Configuration: breaking covalent bonds
Conformation: weak bonds being broken
Cis/Trans is a configuration change
How do you name fatty acids? Where do you start counting?
- # C: #DB (△positions of DB)
- numbered starting with COOH, as carbon #1
What are fatty acids physical properties defined by?
Their hydrocarbon length and degree of saturation
Naturally occurring double bonds have which configuration?
Naturally: cis-configuration
How does the packing of trans unsaturated fatty acids compare to cis unsaturated fatty acids?
Trans looks like saturated in terms of packing, can pack tighter than unsaturated and have higher melting points
How are trans fatty acids formed?
by partial hydrogenation of unsaturated fatty acids and cis-double bond Isomerization to Trans-double bonds.
Name 2 reasons why saturated (animal fat) and trans fats (animal or plants) are bad for health.
1) Saturated Fatty acids increase blood cholesterol levels by providing proper packing domains for cholesterol.
2) Trans-fats do the same, together with increased rigidity around the double bonds
Name 3 reasons why high cholesterol and higher incidence of heart disease are related.
1) Reduced membrane Fluidity
2) Reduced membrane Flexibility
3) Reduced membrane protein Functions
How does solubility and melting point change as the chain length increases?
Solubility: decreases
Melting point: Increases
Why do saturated and unsaturated fatty acids pack differently?
Saturated: orderly way
extensive favorable interactions (Van der Waals)
Unsaturated: pack less regular due to the kink
Less extensive favorable interactions
Why is partial hydrogenation a problem?
- Trans fats
- Reduces the mobility of the FA
- Cholesterol will stick more easily
What kind of lipids are fatty acids found in? What are the responsible for in aqueous solutions?
- Found in complex lipids
- Responsible for the formation of micelles in aqueous solutions
What do acylglycerols result from?
Condensation Reaction between one glycerol sugar with one, two or three fatty acids
In acylglycerols: glycerol and fatty acids are linked by what?
Ester linkage
Lipids containing fatty acids with unsaturated hydrocrabon chain of 20 carbons and 2 cis-double bonds are likely to be what?
Oil at room temperature
Fatty acids with trans-unsaturated hydrocarbon chains of 10 C + 3 double bonds have an approximate melting temperature of?
+ 30oC the double bonds make it have a high melting temperature
What is the ester bond that you form in triacylglycerides in terms of polarity?
Apolar - forms an aggregate if dropped into water, no micelles
How many ester bonds do triacylglycerols have?
3 ester bonds
Compare a simple and a complex/mixed triglyceride.
Simple: if all the fatty acids are the length
Complex: if the fatty acids are different lengths and saturation
Does a simple triacylglyceride have a asymmetric centre? Does mixed?
Simple: NO, no chiral carbon
Mixed: Yes at carbon number 2
What are the solubility and melting point of triacylglycerides determined by?
determined by the nature of the fatty acids that are attached to the glycerol backbone. Whether it is long, saturated or unsaturated will determine the physical property of the triacylglyceride. In the same way that FA determine their own physical properties
Why are triacylglycerides good at storage of lipids?
apolar structure, no water associated with it and a highly reduced structure
What kind of lipid is the most abundant form of metabolic storage in animal cells (fat cells) and in plants (seeds)
Triacylglycerols
Animal and plant triacylglycerols are present in what form?
Insoluble forms
Are triacylglycerols fat or oil?
Both
animal triglycerides are solid, while plant and fish triglycerides are oil at room temp
- Oil is unsaturated,
How do triacylglycerols compare to sugar in terms of energy storage?
Triacylglycerol are considered light-source of energy compared to sugar
Name the 2 reasons why triacylglycerols are key in mammalian survival.
1) Energy storage
2) Hygiene (fat dripping on ash formed bubbles)
Name 2 advantages of fats over polysaccharides.
- Acylglycerides carry more energy per carbon because they are more reduced
- Fatty acids carry less water along because they are nonpolar
How do glucose, glycogen and acylglycerides compare in terms of energy storage?
- Glucose and glycogen are short-term energy needs, quick delivery
= Acylglycerides are for long term (months) energy needs, good storage, slow delivery
Where are triacylglycerols digested? By what?
in the small intestine by the enzyme pancreatic lipase
Where are mono-acylglycerols absorbed? Converted to what? Assembled to what?
absorbed by intestinal cells and converted to
tri-acylglycerols and assembled into lipoproteins
The treatment of triacylglycerols with a SB or SA leads to what?
The hydrolysis of the ester bond between glycerol and fatty acids
- Creates soaps, hand soap, shaving cream
Name 2 ways to hydrolyze acylglycerols. How do they differ?
1) Physiologically with lipases -> energy production
2) Chemical with SA and SB -> fatty acid salts and glycerol used for soaps
How are waxes formed?
by a condensation reaction between long fatty acids
and alcohol hydrocarbon chains
Which lipids do not contain a glycerol backbone?
- Waxes
- Sphingolipids
- Biologically active lipids (prostaglandins, steroids)
What is the melting temperature of waxes? How does it differ from triacylglycerides?
- 60-100oC
- Higher than TG due to their very long hydrocarbon chain
What do waxes act as? What kind of coating do they have?
- Act as metabolic fuel
- Water impermeable coating
What can waxes be broken down with? What does it produce?
Broken down with SA and SB to fatty acids and alcohol hydrocarbons
- You will get some kind of soap, FA can form micelles